Azobenzene photomechanics: prospects and potential applications
- Zahid Mahimwalla,
- Kevin G. Yager,
- Jun-ichi Mamiya,
- Atsushi Shishido,
- Arri Priimagi,
- Christopher J. Barrett
- … show all 6 hide
Purchase on Springer.com
$39.95 / €34.95 / £29.95 *
* Final gross prices may vary according to local VAT.
Abstract
The change in shape inducible in some photo-reversible molecules using light can effect powerful changes to a variety of properties of a host material. This class of reversible light-switchable molecules includes molecules that photo-dimerize, such as coumarins and anthracenes; those that allow intra-molecular photo-induced bond formation, such as fulgides, spiro-pyrans, and diarylethenes; and those that exhibit photo-isomerization, such as stilbenes, crowded alkenes, and azobenzenes. The most ubiquitous natural molecule for reversible shape change, however, and perhaps the inspiration for all artificial bio-mimics, is the rhodopsin/retinal protein system that enables vision, and this is the quintessential reversible photo-switch for performance and robustness. Here, the small retinal molecule embedded in a cage of rhodopsin helices isomerizes from a cis geometry to a trans geometry around a C=C double bond with the absorption of just a single photon. The modest shape change of just a few angstroms is quickly amplified and sets off a cascade of larger shape and chemical changes, eventually culminating in an electrical signal to the brain of a vision event, the energy of the input photon amplified many thousands of times in the process. Complicated biochemical pathways then revert the trans isomer back to cis, and set the system back up for another cascade upon subsequent absorption. The reversibility is complete, and many subsequent cycles are possible. The reversion mechanism back to the initial cis state is complex and enzymatic, hence direct application of the retinal/rhodopsin photo-switch to engineering systems is difficult. Perhaps the best artificial mimic of this strong photo-switching effect however in terms of reversibility, speed, and simplicity of incorporation, is azobenzene. Trans and cis states can be switched in microseconds with low-power light, reversibility of 105 and 106 cycles is routine before chemical fatigue, and a wide variety of molecular architectures is available to the synthetic materials chemist, permitting facile anchoring and compatibility, as well as chemical and physical amplification of the simple geometric change. This review article focuses on photo-mechanical effect taking place in various material systems incorporating azobenzene. The photo-mechanical effect can be defined as reversible change in shape by absorption of light, which results in a significant macroscopic mechanical deformation, and reversible mechanical actuation, of the host material. Thus, we exclude simple thermal expansion effects, reversible but non-mechanical photo-switching or photo-chemistry, as well as the wide range of optical and electro-optical switching effects for which good reviews exist elsewhere. Azobenzene-based material systems are also of great interest for light energy harvesting applications across much of the solar spectrum, yet this emerging field is still in an early enough stage of research output as to not yet warrant review, but we hope that some of the ideas put forward here toward promising future directions of research, will help guide the field.
Look
Inside
Within this Article
- Introduction
- Photoinduced motions and movements
- Photomechanical actuation
- Applications in robotics and micromechanics
- Conclusions and outlook
- References
- References
Related Content
Supplementary Material (0)
References (282)
- Delaire JA, Nakatani K (2000) Linear and nonlinear optical properties of photochromic molecules and materials. Chem Rev 100(5):1817–1846 CrossRef
- Yesodha SK, Sadashiva Pillai CK, Tsutsumi N (2004) Stable polymeric materials for nonlinear optics: a review based on azobenzene systems. Prog Polym Sci 29(1):45–74 CrossRef
- Aoki Ki, Nakagawa M, Ichimura K (2000) Self-assembly of amphoteric azopyridine carboxylic acids: organized structures and macroscopic organized morphology influenced by heat, ph change, and light. J Am Chem Soc 122(44):10997–11004 CrossRef
- Kadota S, Aoki K, Nagano S, Seki T (2005) Photocontrolled microphase separation of block copolymers in two dimensions. J Am Chem Soc 127(23):8266–8267 CrossRef
- Effing JJ, Kwak JCT (1995) Photoswitchable phase separation in hydrophobically modified polyacrylamide/surfactant systems. Angew Chem Int Ed 34(1):88–90 CrossRef
- Yamamoto H, Nishida A, Takimoto T, Nagai A (1990) Photoresponsive peptide and polypeptide systems. VIII. Synthesis and reversible photochromism of azo aromatic poly(l-ornithine). J Polym Sci Part A Pol Chem 28(1):67–74 CrossRef
- Arai K, Kawabata Y (1995) Changes in the sol-gel transformation behavior of azobenzene moiety-containing methyl cellulose irradiated with UV light. Macromol Rapid Commun 16(12):875–880 CrossRef
- Ebralidze TD, Mumladze AN (1990) Light-induced anisotropy in azo-dye-colored materials. Appl Opt 29(4):446–447 CrossRef
- Higuchi M, Minoura N, Kinoshita T (1994) Photocontrol of micellar structure of an azobenzene containing amphiphilic sequential polypeptide. Chem Lett 2:227–230 CrossRef
- Higuchi M, Minoura N, Kinoshita T (1995) Photoinduced structural and functional changes of an azobenzene containing amphiphilic sequential polypeptide. Macromolecules 28(14):4981–4985 CrossRef
- Steinem C, Janshoff A, Vollmer MS, Ghadiri MR (1999) Reversible photoisomerization of self-organized cylindrical peptide assemblies at air-water and solid interfaces. Langmuir 15(11):3956–3964 CrossRef
- Vollmer MS, Clark TD, Steinem C, Ghadiri MR (1999) Photoswitchable hydrogen-bonding in self-organized cylindrical peptide systems. Angew Chem Int Ed 38(11):1598–1601 CrossRef
- Yagai S, Nakajima T, Kishikawa K, Kohmoto S, Karatsu T, Kitamura A (2005) Hierarchical organization of photoresponsive hydrogen-bonded rosettes. J Am Chem Soc 127(31):11134–11139 CrossRef
- Pouliquen G, Tribet C (2005) Light-triggered association of bovine serum albumin and azobenzene-modified poly(acrylic acid) in dilute and semidilute solutions. Macromolecules 39(1):373–383 CrossRef
- Camorani P, Fontana MP (2006) Optical control of structural morphology in azobenzene containing polymeric liquid crystals. Phys Rev E 73(1):011703–011706 CrossRef
- Norikane Y, Hirai Y, Yoshida M (2011) Photoinduced isothermal phase transitions of liquid-crystalline macrocyclic azobenzenes. Chem Commun 47(6):1770–1772 CrossRef
- Wang G, Tong X, Zhao Y (2004) Preparation of azobenzene-containing amphiphilic diblock copolymers for light-responsive micellar aggregates. Macromolecules 37(24):8911–8917 CrossRef
- Ravi P, Sin SL, Gan LH, Gan YY, Tam KC, Xia XL, Hu X (2005) New water soluble azobenzene-containing diblock copolymers: synthesis and aggregation behavior. Polymer 46(1):137–146 CrossRef
- Sin SL, Gan LH, Hu X, Tam KC, Gan YY (2005) Photochemical and thermal isomerizations of azobenzene-containing amphiphilic diblock copolymers in aqueous micellar aggregates and in film. Macromolecules 38(9):3943–3948 CrossRef
- Yoshida E, Ohta M (2005) Preparation of light-stable micelles with azo dyes from a nonamphiphilic random block copolymer. Colloid Polym Sci 283(8):872–879 CrossRef
- Yoshida E, Ohta M (2005) Preparation of micelles with azobenzene at their coronas or cores from nonamphiphilic diblock copolymers. Colloid Polym Sci 283(5):521–531 CrossRef
- Sakai H, Matsumura A, Saji T, Abe M (2001) Active control of vesicle formation with photoelectrochemical switching. Stud Surf Sci Catal 132:505–508 CrossRef
- Tong X, Wang G, Soldera A, Zhao Y (2005) How can azobenzene block copolymer vesicles be dissociated and reformed by light? J Phys Chem B 109(43):20281–20287 CrossRef
- Willner I, Rubin S (1996) Control of the structure and functions of biomaterials by light. Angew Chem Int Ed 35(4):367–385 CrossRef
- Beharry AA, Woolley GA (2011) Azobenzene photoswitches for biomolecules. Chem Soc Rev 40(8):4422–4437 CrossRef
- Montagnoli G, Pieroni O, Suzuki S (1983) Control of peptide chain conformation by photoisomerising chromophores: enzymes and model compounds. Polym Photochem 3(4):279–294 CrossRef
- Yamamoto H, Nishida A (1991) Photoresponsive peptide and polypeptide systems. Part 9. Synthesis and reversible photochromism of azo aromatic poly(l-a,g-diaminobutyric acid). Polym Int 24(3):145–148 CrossRef
- Fissi A, Pieroni O, Balestreri E, Amato C (1996) Photoresponsive polypeptides. Photomodulation of the macromolecular structure in poly(N((phenylazophenyl)sulfonyl)-l-lysine). Macromolecules 29(13):4680–4685 CrossRef
- Fissi A, Pieroni O, Ciardelli F (1987) Photoresponsive polymers—azobenzene-containing poly(l-lysine). Biopolymers 26(12):1993–2007 CrossRef
- Lee W-S, Ueno A (2001) Photocontrol of the catalytic activity of a beta-cyclodextrin bearing azobenzene and histidine moieties as a pendant group. Macromol Rapid Commun 22(6):448–450 CrossRef
- Pearson D, Downard AJ, Muscroft-Taylor A, Abell AD (2007) Reversible photoregulation of binding of α-chymotrypsin to a gold surface. J Am Chem Soc 129(48):14862–14863 CrossRef
- Shinkai S, Minami T, Kusano Y, Manabe O (1983) Photoresponsive crown ethers. 8. Azobenzenophane-type switched-on crown ethers which exhibit an all-or-nothing change in ion-binding ability. J Am Chem Soc 105(7):1851–1856 CrossRef
- Jung JH, Takehisa C, Sakata Y, Kaneda T (1996) p-(4-Nitrophenylazo)phenol dye-bridged permethylated a-cyclodextrin dimer: synthesis and self-aggregation in dilute aqueous solution. Chem Lett 2:147–148 CrossRef
- Yamamura H, Kawai H, Yotsuya T, Higuchi T, Butsugan Y, Araki S, Kawai M, Fujita K (1996) A cyclodextrin derivative with cation carrying ability: heptakis(3,6-anhydro)-b-cyclodextrin 2-O-p-phenylazobenzoate. Chem Lett 9:799–800 CrossRef
- Singh AK, Das J, Majumdar N (1996) Novel bacteriorhodopsin analogs based on azo chromophores. J Am Chem Soc 118(26):6185–6191 CrossRef
- Chen SH, Mastrangelo JC, Shi H, Blanton TN, Bashir-Hashemi A (1997) Novel glass-forming organic materials. 3. Cubane with pendant nematogens, carbazole, and disperse red 1. Macromolecules 30(1):93–97 CrossRef
- Chen SH, Mastrangelo JC, Shi H, Bashir-Hashemi A, Li J, Gelber N (1995) Novel glass-forming organic materials. 1. Adamantane with pendant cholesteryl, disperse red 1, and nematogenic groups. Macromolecules 28(23):7775–7778 CrossRef
- Ichimura K (2000) Photoalignment of liquid-crystal systems. Chem Rev 100(5):1847–1873 CrossRef
- Kumar GS, Neckers DC (1989) Photochemistry of azobenzene-containing polymers. Chem Rev 89(8):1915–1925 CrossRef
- Rau H (1990) Photoisomerization of azobenzenes. In: Rebek J (ed) Photochemistry and photophysics, vol 2. CRC Press, Boca Raton, FL, pp 119–141
- Schulze FW, Petrick HJ, Cammenga HK, Klinge H (1977) Thermodynamic properties of the structural analogs benzo[c]cinnoline, trans-azobenzene, and cis-azobenzene. Z Phys Chem 107(1):1–19 CrossRef
- Mita I, Horie K, Hirao K (1989) Photochemistry in polymer solids. 9. Photoisomerization of azobenzene in a polycarbonate film. Macromolecules 22(2):558–563 CrossRef
- Monti S, Orlandi G, Palmieri P (1982) Features of the photochemically active state surfaces of azobenzene. Chem Phys 71(1):87–99 CrossRef
- Kobayashi T, Degenkolb EO, Rentzepis PM (1979) Picosecond spectroscopy of 1-phenylazo-2-hydroxynaphthalene. J Phys Chem 83(19):2431–2434 CrossRef
- Lednev IK, Ye T-Q, Hester RE, Moore JN (1996) Femtosecond time-resolved UV–Visible Absorption spectroscopy of trans-azobenzene in solution. J Phys Chem 100(32):13338–13341 CrossRef
- Brown EV, Granneman GR (1975) Cis-trans isomerism in pyridyl analogs of azobenzene—kinetic and molecular-orbital analysis. J Am Chem Soc 97(3):621–627 CrossRef
- Haberfield P, Block PM, Lux MS (1975) Enthalpies of solvent transfer of transition-states in cis-trans isomerization of azo-compounds - rotation vs nitrogen inversion mechanism. J Am Chem Soc 97(20):5804–5806 CrossRef
- Kerzhner BK, Kofanov VI, Vrubel TL (1983) Photoisomerization of aromatic azo compounds adsorbed on a hydroxylated surface. Zh Obshch Khim 53(10):2303–2306
- Funke U, Gruetzmacher HF (1987) Dithiadiaza[n.2]paracyclophenes. Tetrahedron 43(16):3787–3795 CrossRef
- Hartley GS (1937) Cis form of azobenzene. Nature 140:281 CrossRef
- Hartley GS (1938) Cis form of azobenzene and the velocity of the thermal cis–trans conversion of azobenzene and some derivatives. J Chem Soc 1938:633–642 CrossRef
- Fischer E (1967) Calculation of photostationary states in systems A-B when only A is known. J Phys Chem 71(11):3704–3706 CrossRef
- Rau H, Greiner G, Gauglitz G, Meier H (1990) Photochemical quantum yields in the A-B system when only the spectrum of A is known. J Phys Chem 94(17):6523–6524 CrossRef
- Gabor G, Fischer E (1971) Spectra and cis–trans isomerism in highly dipolar derivatives of azobenzene. J Phys Chem 75(4):581–583 CrossRef
- Eisenbach CD (1980) Cis-trans isomerization of aromatic azo chromophores, incorporated in the hard segments of poly(ester urethane)s. Macromol Rapid Commun 1(5):287–292 CrossRef
- Hair SR, Taylor GA, Schultz LW (1990) An easily implemented flash-photolysis experiment for the physical-chemistry laboratory—the isomerization of 4-anilino-4’-nitroazobenzene. J Chem Educ 67(8):709–712 CrossRef
- Beltrame PL, Paglia ED, Castelli A, Tantardini GF, Seves A, Marcandalli B (1993) Thermal cis-trans-isomerization of azo dyes in poly(methyl methacrylate) matrix—a kinetic-study. J Appl Polym Sci 49(12):2235–2239 CrossRef
- Magennis SW, Mackay FS, Jones AC, Tait KM, Sadler PJ (2005) Two-photon-induced photoisomerization of an azo dye. Chem Mater 17(8):2059–2062 CrossRef
- Rau H, Lueddecke E (1982) On the rotation-inversion controversy on photoisomerization of azobenzenes. experimental proof of inversion. J Am Chem Soc 104(6):1616–1620 CrossRef
- Naito T, Horie K, Mita I (1991) Photochemistry in polymer solids. 11. The effects of the size of reaction groups and the mode of photoisomerization on photochromic reactions in polycarbonate film. Macromolecules 24(10):2907–2911 CrossRef
- Liu ZF, Morigaki K, Enomoto T, Hashimoto K, Fujishima A (1992) Kinetic studies on the thermal cis-trans isomerization of an azo compound in the assembled monolayer film. J Phys Chem 96(4):1875–1880 CrossRef
- Altomare A, Ciardelli F, Tirelli N, Solaro R (1997) 4-Vinylazobenzene: polymerizability and photochromic properties of its polymers. Macromolecules 30(5):1298–1303 CrossRef
- Ho C-H, Yang K-N, Lee S-N (2001) Mechanistic study of trans-cis isomerization of the substituted azobenzene moiety bound on a liquid-crystalline polymer. J Polym Sci, Part A: Polym Chem 39(13):2296–2307 CrossRef
- Xie S, Natansohn A, Rochon P (1993) Recent developments in aromatic azo polymers research. Chem Mater 5(4):403–411 CrossRef
- Jursic BS (1996) Ab initio and density functional theory study of the diazene isomerization. Chem Phys Lett 261(1–2):13–17 CrossRef
- Angeli C, Cimiraglia R, Hofmann H-J (1996) On the competition between the inversion and rotation mechanisms in the cis-trans thermal isomerization of diazene. Chem Phys Lett 259(3–4):276–282 CrossRef
- Natansohn A, Rochon P (2002) Photoinduced motions in azo-containing polymers. Chem Rev 102(11):4139–4176 CrossRef
- Viswanathan NK, Balasubramanian S, Li L, Tripathy SK, Kumar J (1999) A detailed investigation of the polarization-dependent surface-relief-grating formation process on azo polymer films. Jpn J Appl Phys 38(10):5928–5937 CrossRef
- Yager KG, Barrett CJ (2001) All-optical patterning of azo polymer films. Curr Opin Solid State Mater Sci 5(6):487–494 CrossRef
- Uznanski P, Kryszewski M, Thulstrup EW (1991) Linear dichroism and trans-cis photo-isomerization studies of azobenzene molecules in oriented polyethylene matrix. Eur Polym J 27(1):41–43 CrossRef
- de Lange JJ, Robertson JM, Woodward I (1939) X-ray crystal analysis of trans-azobenzene. Proc Roy Soc A Math Phys Eng Sci 171:398–410 CrossRef
- Hampson GC, Robertson JM (1941) Bond length and resonance in the cis-azobenzene molecule. J Chem Soc 2:409–413 CrossRef
- Brown CJ (1966) A refinement of the crystal structure of azobenzene. Acta Cryst 21(1):146–152 CrossRef
- Naito T, Horie K, Mita I (1993) Photochemistry in polymer solids: 12. Effects of main-chain structures and formation of hydrogen bonds on photoisomerization of azobenzene in various polymer films. Polymer 34(19):4140–4145 CrossRef
- Paik CS, Morawetz H (1972) Photochemical and thermal isomerization of azoaromatic residues in the side chains and the backbone of polymers in bulk. Macromolecules 5(2):171–177 CrossRef
- Lamarre L, Sung CSP (1983) Studies of physical aging and molecular motion by azochromophoric labels attached to the main chains of amorphous polymers. Macromolecules 16(11):1729–1736 CrossRef
- Weiss RG, Ramamurthy V, Hammond GS (1993) Photochemistry in organized and confining media: a model. Acc Chem Res 25(10):530–536 CrossRef
- Hugel T, Holland NB, Cattani A, Moroder L, Seitz M, Gaub HE (2002) Single-molecule optomechanical cycle. Science 296(5570):1103–1106 CrossRef
- Holland NB, Hugel T, Neuert G, Cattani-Scholz A, Renner C, Oesterhelt D, Moroder L, Seitz M, Gaub HE (2003) Single molecule force spectroscopy of azobenzene polymers: switching elasticity of single photochromic macromolecules. Macromolecules 36(6):2015–2023 CrossRef
- Neuert G, Hugel T, Netz RR, Gaub HE (2005) Elasticity of poly(azobenzene-peptides). Macromolecules 39(2):789–797 CrossRef
- Asakawa M, Ashton PR, Balzani V, Brown CL, Credi A, Matthews OA, Newton SP, Raymo FM, Shipway AN, Spencer N, Quick A, Stoddart JF, White AJP, Williams DJ (1999) Photoactive azobenzene-containing supramolecular complexes and related interlocked molecular compounds. Chem A Eur J 5(3):860–875 CrossRef
- Balzani V, Credi A, Marchioni F, Stoddart JF (2001) Artificial molecular-level machines. Dethreading-rethreading of a pseudorotaxane powered exclusively by light energy. Chem Commun 18:1860–1861 CrossRef
- Tsuchiya S (1999) Intramolecular electron transfer of diporphyrins comprised of electron-deficient porphyrin and electron-rich porphyrin with photocontrolled isomerization. J Am Chem Soc 121(1):48–53 CrossRef
- Masiero S, Lena S, Pieraccini S, Spada GP (2008) The direct conversion of light into continuous mechanical energy by photoreversible self-assembly: a prototype of a light-powered engine. Angew Chem Int Ed 47(17):3184–3187 CrossRef
- Fujiwara M, Akiyama M, Hata M, Shiokawa K, Nomura R (2008) Photoinduced acceleration of the effluent rate of developing solvents in azobenzene-tethered silica gel. ACS Nano 2(8):1671–1681 CrossRef
- Pakula C, Zaporojtchenko V, Strunskus T, Zargarani D, Herges R, Faupel F (2010) Reversible light-controlled conductance switching of azobenzene-based metal/polymer nanocomposites. Nanotechnology 21(46):465201 CrossRef
- Raimondo C, Reinders F, Soydaner U, Mayor M, Samorì P (2010) Light-responsive reversible solvation and precipitation of gold nanoparticles. Chem Commun 46(7):1147–1149 CrossRef
- Kimoto A, Iwasaki K, Abe J (2010) Formation of photoresponsive gold nanoparticle networks via click chemistry. Photochem Photobiol Sci 9(2):152–156 CrossRef
- Higuchi M, Minoura N, Kinoshita T (1995) Photo-responsive behavior of a monolayer composed of an azobenzene containing polypeptide in the main-chain. Colloid Polym Sci 273(11):1022–1027 CrossRef
- Siewierski LM, Brittain WJ, Petrash S, Foster MD (1996) Photoresponsive monolayers containing in-chain azobenzene. Langmuir 12(24):5838–5844 CrossRef
- Stiller B, Knochenhauer G, Markava E, Gustina D, Muzikante I, Karageorgiev P, Brehmer L (1999) Self-assembled monolayers of novel azobenzenes for optically induced switching. Mater Sci Eng, C 8–9:385–389 CrossRef
- Moller G, Harke M, Motschmann H, Prescher D (1998) Controlling microdroplet formation by light. Langmuir 14(18):4955–4957 CrossRef
- Feng CL, Zhang YJ, Jin J, Song YL, Xie LY, Qu GR, Jiang L, Zhu DB (2001) Reversible wettability of photoresponsive fluorine-containing azobenzene polymer in Langmuir–Blodgett films. Langmuir 17(15):4593–4597 CrossRef
- Chen T, Xu S, Zhang F, Evans DG, Duan X (2009) Formation of photo- and thermo-stable layered double hydroxide films with photo-responsive wettability by intercalation of functionalized azobenzenes. Chem Eng Sci 64(21):4350–4357 CrossRef
- Delorme N, Bardeau J-F, Bulou A, Poncin-Epaillard F (2005) Azobenzene-containing monolayer with photoswitchable wettability. Langmuir 21(26):12278–12282 CrossRef
- Jiang WH, Wang GJ, He YN, Wang XG, An YL, Song YL, Jiang L (2005) Photo-switched wettability on an electrostatic self-assembly azobenzene monolayer. Chem Commun 28:3550–3552 CrossRef
- Ichimura K, Oh S-K, Nakagawa M (2000) Light-driven motion of liquids on a photoresponsive surface. Science 288(5471):1624–1626 CrossRef
- Diguet A, Guillermic R-M, Magome N, Saint-Jalmes A, Chen Y, Yoshikawa K, Baigl D (2009) Photomanipulation of a droplet by the chromocapillary effect. Angew Chem Int Ed 48(49):9281–9284 CrossRef
- Sarkar N, Sarkar A, Sivaram S (2001) Isomerization behavior of aromatic azo chromophores bound to semicrystalline polymer films. J Appl Polym Sci 81(12):2923–2928 CrossRef
- Fujita T, Iyi N, Klapyta Z (1998) Preparation of azobenzene-mica complex and its photoresponse to ultraviolet irradiation. Mater Res Bull 33(11):1693–1701 CrossRef
- Fujita T, Iyi N, Klapyta Z (2001) Optimum conditions for photoresponse of azobenzene-organophilic tetrasilicic mica complexes. Mater Res Bull 36(3–4):557–571 CrossRef
- Yager KG, Tanchak OM, Godbout C, Fritzsche H, Barrett CJ (2006) Photomechanical effects in azo-polymers studied by neutron reflectometry. Macromolecules 39(26):9311–9319 CrossRef
- Tanchak OM, Barrett CJ (2005) Light-induced reversible volume changes in thin films of azo polymers: the photomechanical effect. Macromolecules 38(25):10566–10570 CrossRef
- Yager KG, Tanchak OM, Barrett CJ, Watson MJ, Fritzsche H (2006) Temperature-controlled neutron reflectometry sample cell suitable for study of photoactive thin films. Rev Sci Instrum 77(4):045106 CrossRef
- Eisenbach CD (1980) Isomerization of aromatic azo chromophores in poly(ethyl acrylate) networks and photomechanical effect. Polymer 21(10):1175–1179 CrossRef
- Agolini F, Gay FP (1970) Synthesis and properties of azoaromatic polymers. Macromolecules 3(3):349–351 CrossRef
- Yu Y, Nakano M, Ikeda T (2003) Photomechanics: directed bending of a polymer film by light. Nature 425:145 CrossRef
- Ikeda T, Nakano M, Yu Y, Tsutsumi O, Kanazawa A (2003) Anisotropic bending and unbending behavior of azobenzene liquid-crystalline gels by light exposure. Adv Mater 15(3):201–205 CrossRef
- Yu YL, Nakano M, Maeda T, Kondo M, Ikeda T (2005) Precisely direction-controllable bending of cross-linked liquid-crystalline polymer films by light. Mol Cryst Liq Cryst 436:1235–1244 CrossRef
- Bai S, Zhao Y (2001) Azobenzene-containing thermoplastic elastomers: coupling mechanical and optical effects. Macromolecules 34(26):9032–9038 CrossRef
- Rochon P, Batalla E, Natansohn A (1995) Optically induced surface gratings on azoaromatic polymer films. Appl Phys Lett 66(2):136–138 CrossRef
- Kim DY, Tripathy SK, Li L, Kumar J (1995) Laser-induced holographic surface relief gratings on nonlinear optical polymer films. Appl Phys Lett 66(10):1166–1168 CrossRef
- Bian S, Li L, Kumar J, Kim DY, Williams J, Tripathy SK (1998) Single laser beam-induced surface deformation on azobenzene polymer films. Appl Phys Lett 73(13):1817–1819 CrossRef
- Kumar J, Li L, Jiang XL, Kim DY, Lee TS, Tripathy S (1998) Gradient force: the mechanism for surface relief grating formation in azobenzene functionalized polymers. Appl Phys Lett 72(17):2096–2098 CrossRef
- Viswanathan NK, Kim DY, Bian S, Williams J, Liu W, Li L, Samuelson L, Kumar J, Tripathy SK (1999) Surface relief structures on azo polymer films. J Mater Chem 9(9):1941–1955 CrossRef
- Labarthet FL, Bruneel JL, Buffeteau T, Sourisseau C (2004) Chromophore orientations upon irradiation in gratings inscribed on azo-dye polymer films: a combined AFM and confocal Raman microscopic study. J Phys Chem B 108(22):6949–6960 CrossRef
- Lagugne-Labarthet F, Bruneel JL, Rodriguez V, Sourisseau C (2004) Chromophore orientations in surface relief gratings with second-order nonlinearity as studied by confocal polarized Raman microspectrometry. J Phys Chem B 108(4):1267–1278 CrossRef
- Labarthet FL, Bruneel JL, Buffeteau T, Sourisseau C, Huber MR, Zilker SJ, Bieringer T (2000) Photoinduced orientations of azobenzene chromophores in two distinct holographic diffraction gratings as studied by polarized Raman confocal microspectrometry. Phys Chem Chem Phys 2(22):5154–5167 CrossRef
- Henneberg O, Geue T, Pietsch U, Saphiannikova M, Winter B (2004) Investigation of azobenzene side group orientation in polymer surface relief gratings by means of photoelectron spectroscopy. Appl Phys Lett 84(9):1561–1563 CrossRef
- Saphiannikova M, Neher D (2005) Thermodynamic theory of light-induced material transport in amorphous azobenzene polymer films. J Phys Chem B 109(41):19428–19436 CrossRef
- Toshchevikov V, Saphiannikova M, Heinrich G (2009) Microscopic theory of light-induced deformation in amorphous side-chain azobenzene polymers. J Phys Chem B 113(15):5032–5045 CrossRef
- Vapaavuori J, Valtavirta V, Alasaarela T, Mamiya JI, Priimagi A, Shishido A, Kaivola M (2011) Efficient surface structuring and photoalignment of supramolecular polymer-azobenzene complexes through rational chromophore design. J Mater Chem 21(39):15437–15441 CrossRef
- Pietsch U, Rochon P, Natansohn A (2000) Formation of a buried lateral density grating in azobenzene polymer films. Adv Mater 12(15):1129–1132 CrossRef
- Geue T, Henneberg O, Grenzer J, Pietsch U, Natansohn A, Rochon P, Finkelstein K (2002) Formation of a buried density grating on thermal erasure of azobenzene polymer surface gratings. Coll Surf A 198–200:31–36 CrossRef
- Geue TM, Saphiannikova MG, Henneberg O, Pietsch U, Rochon PL, Natansohn AL (2003) X-ray investigations of formation efficiency of buried azobenzene polymer density gratings. J Appl Phys 93(6):3161–3166 CrossRef
- Pietsch U (2002) X-ray and visible light scattering from light-induced polymer gratings. Phys Rev B 66(15):155430 CrossRef
- Barrett CJ, Natansohn AL, Rochon PL (1996) Mechanism of optically inscribed high-efficiency diffraction gratings in azo polymer films. J Phys Chem 100(21):8836–8842 CrossRef
- Priimagi A, Lindfors K, Kaivola M, Rochon P (2009) efficient surface-relief gratings in hydrogen-bonded polymer-azobenzene complexes. ACS Appl Mater Interfaces 1(6):1183–1189 CrossRef
- Wang X, Balasubramanian S, Kumar J, Tripathy SK, Li L (1998) Azo chromophore-functionalized polyelectrolytes. 1. Synthesis, characterization, and photoprocessing. Chem Mater 10(6):1546–1553 CrossRef
- He J-A, Bian S, Li L, Kumar J, Tripathy SK, Samuelson LA (2000) Surface relief gratings from electrostatically layered azo dye films. Appl Phys Lett 76(22):3233–3235 CrossRef
- Lee S-H, Balasubramanian S, Kim DY, Viswanathan NK, Bian S, Kumar J, Tripathy SK (2000) Azo polymer multilayer films by electrostatic self-assembly and layer-by-layer post azo functionalization. Macromolecules 33(17):6534–6540 CrossRef
- Zhang Q, Wang X, Barrett CJ, Bazuin CG (2009) Spacer-free ionic dye-polyelectrolyte complexes: influence of molecular structure on liquid crystal order and photoinduced motion. Chem Mater 21(14):3216–3227 CrossRef
- Yang SZ, Li L, Cholli AL, Kumar J, Tripathy SK (2001) Photoinduced surface relief gratings on azocellulose films. J Macromol Sci, Pure Appl Chem 38(12):1345–1354 CrossRef
- Yang S, Jacob MM, Li L, Yang K, Cholli AL, Kumar J, Tripathy SK (2002) Azobenzene-modified cellulose. Polymer News 27:368–372
- Yang SZ, Li L, Cholli AL, Kumar J, Tripathy SK (2003) Ambenzene-modified poly(l-glutamic acid) (AZOPLGA): its conformational and photodynamic properties. Biomacromolecules 4(2):366–371 CrossRef
- Nakano H, Tanino T, Takahashi T, Ando H, Shirota Y (2008) Relationship between molecular structure and photoinduced surface relief grating formation using azobenzene-based photochromic amorphous molecular materials. J Mater Chem 18(2):242–246 CrossRef
- Walker R, Audorff H, Kador L, Schmidt HW (2009) Synthesis and structure-property relations of a series of photochromic molecular classes for controlled and efficient formation of surface relief nanostructures. Adv Funct Mater 19(16):2630–2638 CrossRef
- Ubukata T, Takahashi K, Yokoyama Y (2007) Photoinduced surface relief structures formed on polymer films doped with photochromic spiropyrans. J Phys Org Chem 20(11):981–984 CrossRef
- Ubukata T, Fujii S, Yokoyama Y (2009) Reversible phototriggered micromanufacturing using amorphous photoresponsive spirooxazine film. J Mater Chem 19(21):3373–3377 CrossRef
- Zettsu N, Ubukata T, Seki T, Ichimura K (2001) Soft crosslinkable azo polymer for rapid surface relief formation and persistent fixation. Adv Mater 13(22):1693–1697 CrossRef
- Li W, Nagano S, Seki T (2009) Photo-crosslinkable liquid-crystalline azo-polymer for surface relief gratings and persistent fixation. New J Chem 33(6):1343–1348 CrossRef
- Goldenberg LM, Kulikovsky L, Kulikovska O, Stumpe J (2009) New materials with detachable azobenzene: effective, colourless and extremely stable surface relief gratings. J Mater Chem 19(43):8068–8071 CrossRef
- Zettsu N, Ogasawara T, Mizoshita N, Nagano S, Seki T (2008) Photo-triggered surface relief grating formation in supramolecular liquid crystalline polymer systems with detachable azobenzene units. Adv Mater 20(3):516–521 CrossRef
- Tripathy SK, Viswanathan NK, Balasubramanian S, Kumar J (2000) Holographic fabrication of polarization selective diffractive optical elements on azopolymer film. Polym Adv Technol 11(8–12):570–574 CrossRef
- Rochon P, Natansohn A, Callendar CL, Robitaille L (1997) Guided mode resonance filters using polymer films. Appl Phys Lett 71(8):1008–1010 CrossRef
- Stockermans RJ, Rochon PL (1999) Narrow-band resonant grating waveguide filters constructed with azobenzene polymers. Appl Opt 38(17):3714–3719 CrossRef
- Alasaarela T, Zheng D, Huang L, Priimagi A, Bai B, Tervonen A, Honkanen S, Kuittinen M, Turunen J (2011) Single-layer one-dimensional nonpolarizing guided-mode resonance filters under normal incidence. Opt Lett 36(13):2411–2413 CrossRef
- Paterson J, Natansohn A, Rochon P, Callendar CL, Robitaille L (1996) Optically inscribed surface relief diffraction gratings on azobenzene-containing polymers for coupling light into slab waveguides. Appl Phys Lett 69(22):3318–3320 CrossRef
- Nagata T, Matsui T, Ozaki M, Yoshino K, Kajzar F (2001) Novel optical properties of conducting polymer-photochromic polymer systems. Synthetic Met 119(1–3):607–608 CrossRef
- Dumarcher V, Rocha L, Denis C, Fiorini C, Nunzi J-M, Sobel F, Sahraoui B, Gindre D (2000) Polymer thin-film distributed feedback tunable lasers. J Opt A: Pure Appl Opt 2(4):279–283 CrossRef
- Rocha L, Dumarcher V, Denis C, Raimond P, Fiorini C, Nunzi JM (2001) Laser emission in periodically modulated polymer films. J Appl Phys 89(5):3067–3069 CrossRef
- Ubukata T, Isoshima T, Hara M (2005) Wavelength-programmable organic distributed-feedback laser based on a photoassisted polymer-migration system. Adv Mater 17(13):1630–1633 CrossRef
- Egami C, Kawata Y, Aoshima Y, Alasfar S, Sugihara O, Fujimura H, Okamoto N (2000) Two-stage optical data storage in azo polymers. Jpn J Appl Phys 39(3B):1558–1561 CrossRef
- Harada K, Itoh M, Yatagai T, Kamemaru SI (2005) Application of surface relief hologram using azobenzene containing polymer film. Opt Rev 12(2):130–134 CrossRef
- Ramanujam PS, Pedersen M, Hvilsted S (1999) Instant holography. Appl Phys Lett 74(21):3227–3229 CrossRef
- Na SI, Kim SS, Jo J, Oh SH, Kim J, Kim DY (2008) Efficient polymer solar cells with surface relief gratings fabricated by simple soft lithography. Adv Funct Mater 18(24):3956–3963 CrossRef
- Gritsai Y et al (2008) 3D structures using surface relief gratings of azobenzene materials. J Opt A: Pure Appl Opt 10(12):125304 CrossRef
- Neumann J, Wieking KS, Kip D (1999) Direct laser writing of surface reliefs in dry, self-developing photopolymer films. Appl Opt 38(25):5418–5421 CrossRef
- Li XT, Natansohn A, Rochon P (1999) Photoinduced liquid crystal alignment based on a surface relief grating in an assembled cell. Appl Phys Lett 74(25):3791–3793 CrossRef
- Kim M-H, Kim J-D, Fukuda T, Matsuda H (2000) Alignment control of liquid crystals on surface relief gratings. Liq Cryst 27(12):1633–1640 CrossRef
- Parfenov A, Tamaoki N, Ohnishi S (2000) Photoinduced alignment of nematic liquid crystal on the polymer surface microrelief. J Appl Phys 87(4):2043–2045 CrossRef
- Parfenov A, Tamaoki N, Ohni-Shi S (2001) Photoinduced alignment of nematic liquid crystal on the polymer surface microrelief. Mol Cryst Liq Cryst 359:487–495
- Kaneko F, Kato T, Baba A, Shinbo K, Kato K, Advincula RC (2002) Photo-induced fabrication of surface relief gratings in alternate self-assembled films containing azo dye and alignments of LC molecules. Coll Surf A 198:805–810 CrossRef
- Ishow E, Brosseau A, Clavier G, Nakatani K, Pansu RB, Vachon J-J, Tauc P, Chauvat D, Mendonça CR, Piovesan E (2007) Two-photon fluorescent holographic rewritable micropatterning. J Am Chem Soc 129(29):8970–8971 CrossRef
- Chen X, Liu B, Zhang H, Guan S, Zhang J, Zhang W, Chen Q, Jiang Z, Guiver MD (2009) Fabrication of fluorescent holographic micropatterns based on azobenzene-containing host-guest complexes. Langmuir 25(18):10444–10446 CrossRef
- Ye YH, Badilescu S, Truong VV, Rochon P, Natansohn A (2001) Self-assembly of colloidal spheres on patterned substrates. Appl Phys Lett 79(6):872–874 CrossRef
- Yi DK, Kim MJ, Kim DY (2002) Surface relief grating induced colloidal crystal structures. Langmuir 18(6):2019–2023 CrossRef
- Yi DK, Seo E-M, Kim D-Y (2002) Fabrication of a mesoscale wire: sintering of a polymer colloid arrayed inside a one-dimensional groove pattern. Langmuir 18(13):5321–5323 CrossRef
- Noel S, Batalla E, Rochon P (1996) A simple method for the manufacture of mesoscopic metal wires. J Mater Res 11(4):865–867 CrossRef
- Kim SS, Chun C, Hong JC, Kim DY (2006) Well-ordered TiO2 nanostructures fabricated using surface relief gratings on polymer films. J Mater Chem 16(4):370–375 CrossRef
- Morikawa Y, Nagano S, Watanabe K, Kamata K, Iyoda T, Seki T (2006) Optical alignment and patterning of nanoscale microdomains in a block copolymer thin film. Adv Mater 18(7):883–886 CrossRef
- Liu B, Wang M, He Y, Wang X (2006) Duplication of photoinduced azo polymer surface-relief gratings through a soft lithographic approach. Langmuir 22(17):7405–7410 CrossRef
- Ye G, Li X, Wang X (2010) Diffraction grating of hydrogel functionalized with glucose oxidase for glucose detection. Chem Commun 46(22):3872–3874 CrossRef
- Lee S, Kang HS, Park JK (2011) High-resolution patterning of various large-area, highly ordered structural motifs by directional photofluidization lithography: sub-30-nm line, ellipsoid, rectangle, and circle arrays. Adv Funct Mater 21(10):1770–1778 CrossRef
- Lee S, Shin J, Lee YH, Fan S, Park JK (2010) Directional photofluidization lithography for nanoarchitectures with controlled shapes and sizes. Nano Lett 10(1):296–304 CrossRef
- Kravchenko A, Shevchenko A, Ovchinnikov V, Priimagi A, Kaivola M (2011) Optical interference lithography using azobenzene-functionalized polymers for micro- and nanopatterning of silicon. Adv Mater 23(36):4174–4177 CrossRef
- Ikawa T, Kato Y, Yamada T, Shiozawa M, Narita M, Mouri M, Hoshino F, Watanabe O, Tawata M, Shimoyama H (2010) Virus-templated photoimprint on the surface of an azobenzene-containing polymer. Langmuir 26(15):12673–12679 CrossRef
- Watanabe O, Ikawa T, Hasegawa M, Tsuchimori M, Kawata Y, Egami C, Sugihara O, Okamoto N (2000) Transcription of near-field induced by photo-irradiation on a film of azo-containing urethane-urea copolymer. Mol Cryst Liq Cryst 345:629–634
- Ikawa T, Mitsuoka T, Hasegawa M, Tsuchimori M, Watanabe O, Kawata Y, Egami C, Sugihara O, Okamoto N (2000) Optical near field induced change in viscoelasticity on an azobenzene-containing polymer surface. J Phys Chem B 104(39):9055–9058 CrossRef
- Hasegawa M, Ikawa T, Tsuchimori M, Watanabe O, Kawata Y (2001) Topographical nanostructure patterning on the surface of a thin film of polyurethane containing azobenzene moiety using the optical near field around polystyrene spheres. Macromolecules 34(21):7471–7476 CrossRef
- Hasegawa M, Keum C-D, Watanabe O (2002) Enhanced photofabrication of a surface nanostructure on azobenzene-functionalized polymer films with evaporated gold nanoislands. Adv Mater 14(23):1738–1741 CrossRef
- Keum CD, Ikawa T, Tsuchimori M, Watanabe O (2003) Photodeformation behavior of photodynamic polymers bearing azobenzene moieties in their main and/or side chain. Macromolecules 36(13):4916–4923 CrossRef
- Fukuda T, Sumaru K, Kimura T, Matsuda H, Narita Y, Inoue T, Sato F (2001) Observation of optical near-field as photo-induced surface relief formation. Jpn J Appl Phys 40(8B):L900–L902 CrossRef
- Galarreta BC, Rupar I, Young A, Lagugné-Labarthet F (2011) Mapping hot-spots in hexagonal arrays of metallic nanotriangles with azobenzene polymer thin films. J Phys Chem C 115(31):15318–15323 CrossRef
- Hubert C, Rumyantseva A, Lerondel G, Grand J, Kostcheev S, Billot L, Vial A, Bachelot R, Royer P, Chang SH, Gray SK, Wiederrecht GP, Schatz GC (2005) Near-field photochemical imaging of noble metal nanostructures. Nano Lett 5(4):615–619 CrossRef
- Camacho-Lopez M, Finkelmann H, Palffy-Muhoray P, Shelley M (2004) Fast liquid-crystal elastomer swims into the dark. Nat Mater 3(5):307–310 CrossRef
- Bublitz D, Helgert M, Fleck B, Wenke L, Hvilsted S, Ramanujam PS (2000) Photoinduced deformation of azobenzene polyester films. Appl Phys B: Lasers Opt 70(6):863–865 CrossRef
- Ji HF, Feng Y, Xu XH, Purushotham V, Thundat T, Brown GM (2004) Photon-driven nanomechanical cyclic motion. Chem Commun 22:2532–2533 CrossRef
- White TJ, Tabiryan NV, Serak SV, Hrozhyk UA, Tondiglia VP, Koerner H, Vaia RA, Bunning TJ (2008) A high frequency photodriven polymer oscillator. Soft Matter 4(9):1796–1798 CrossRef
- White TJ, Serak SV, Tabiryan NV, Vaia RA, Bunning TJ (2009) Polarization-controlled, photodriven bending in monodomain liquid crystal elastomer cantilevers. J Mater Chem 19(8):1080–1085 CrossRef
- Serak S, Tabiryan N, Vergara R, White TJ, Vaia RA, Bunning TJ (2010) Liquid crystalline polymer cantilever oscillators fueled by light. Soft Matter 6(4):779–783 CrossRef
- Chen M, Huang H, Zhu Y, Liu Z, Xing X, Cheng F, Yu Y (2010) Photodeformable CLCP material: study on photo-activated microvalve applications. Appl Phys A Mater Sci Proc 102(3):667–672
- Yamada M, Kondo M, Mamiya JI, Yu Y, Kinoshita M, Barrett CJ, Ikeda T (2008) Photomobile polymer materials: towards light-driven plastic motors. Angew Chem Int Ed 47(27):4986–4988 CrossRef
- Blair HS, Ivor Pogue H (1982) Photomechanical effects in polymers containing 6′-nitro-1,3,3-trimethyl-spiro-(2′H-1′-benzopyran -2,2′-indoline). Polymer 23(5):779–783 CrossRef
- Blair HS, Pague HI, Riordan JE (1980) Photoresponsive effects in azo polymers. Polymer 21(10):1195–1198 CrossRef
- Menzel H, Weichart B, Hallensleben ML (1992) Langmuir–Blodgett-films of photochromic polyglutamates-II. Synthesis and spreading behaviour of photochromic polyglutamates with alkylspacers and -tails of different length. Polym Bull 27(6):637–644 CrossRef
- Menzel H (1994) Langmuir–Boldgett-films of photochromic polyglutamates. 7. The photomechanical effect in monolayers of polyglutamate with azobenzene moieties in the side-chains. Macromol Chem Phys 195(12):3747–3757 CrossRef
- Seki T, Tamaki T (1993) Photomechanical effect in monolayers of azobenzene side-chain polymers. Chem Lett 10:1739–1742 CrossRef
- Seki T, Sekizawa H, Fukuda RI, Tamaki T, Yokoi M, Ichimura K (1996) Features of photomechanical response in monolayers composed of a charged amphiphilic azobenzene polymer. Polym J 28(7):613–618 CrossRef
- Seki T, Ichimura K, Fukuda RI, Tamaki T (1996) Photomechanical behaviour of monolayers of azobenzene derivatives. Thin Solid Films 284–285:365–367 CrossRef
- Seki T (2004) Dynamic photoresponsive functions in organized layer systems comprised of azobenzene-containing polymers. Polym J 36(6):435–454 CrossRef
- Seki T, Tanaka K, Ichimura K (1997) Photomechanical response in monolayered polymer films on mica at high humidity. Macromolecules 30(20):6401–6403 CrossRef
- Seki T, Sekizawa H, Morino SY, Ichimura K (1998) Inherent and cooperative photomechanical motions in monolayers of an azobenzene containing polymer at the air-water interface. J Phys Chem B 102(27):5313–5321 CrossRef
- Kago K, Fürst M, Matsuoka H, Yamaoka H, Seki T (1999) Direct observation of photoisomerization of a polymer monolayer on a water surface by X-ray reflectometry. Langmuir 15(7):2237–2240 CrossRef
- Seki T, Kojima JY, Ichimura K (2000) Multifarious photoinduced morphologies in monomolecular films of azobenzene side chain polymer on mica. Macromolecules 33(7):2709–2717 CrossRef
- Kago K, Seki T, Schücke RR, Mouri E, Matsuoka H, Yamaoka H (2002) Nanostructure of a photochromic polymer/liquid crystal hybrid monolayer on a water surface observed by in situ X-ray reflectometry. Langmuir 18(10):3875–3879 CrossRef
- Seki T, Fukuchi T, Ichimura K (2002) Role of hydrogen bonding in azobenzene-urea assemblies. The packing state and photoresponse behavior in Langmuir monolayers. Langmuir 18(14):5462–5467 CrossRef
- Klajn R (2010) Immobilized azobenzenes for the construction of photoresponsive materials. Pure Appl Chem 82(12):2247–2276 CrossRef
- Liu C, Chun SB, Mather PT, Zheng L, Haley EH, Coughlin EB (2002) Chemically cross-linked polycyclooctene: synthesis, characterization, and shape memory behavior. Macromolecules 35(27):9868–9874 CrossRef
- Otero TF, Cortés MT (2003) Artificial muscles with tactile sensitivity. Adv Mater 15(4):279–282 CrossRef
- Fukushima T, Asaka K, Kosaka A, Aida T (2005) Fully plastic actuator through layer-by-layer casting with ionic-liquid-based bucky gel. Angew Chem Int Ed 44(16):2410–2413 CrossRef
- Gao J, Sansiñena JM, Wang HL (2003) Tunable polyaniline chemical actuators. Chem Mater 15(12):2411–2418 CrossRef
- Merian E (1966) Steric factors influencing the dyeing of hydrophobic fibers. Text Res J 36(7):612–618 CrossRef
- Irie M (1990) Photoresponsive polymers. Adv Polym Sci 94:26–67
- Smets GaD F (1974) Chemical reactions in solid polymeric systems. Photomechanical phenomena. Pure Appl Chem 39(1–2):225–238 CrossRef
- Matějka L, Dušek K, Ilavský M (1979) The thermal effect in the photomechanical conversion of a photochromic polymer. Polym Bull 1(9):659–664 CrossRef
- Matějka L, Ilavský M, Dušek K, Wichterle O (1981) Photomechanical effects in crosslinked photochromic polymers. Polymer 22(11):1511–1515 CrossRef
- Matějka L, Dušek K (1981) Photochromic polymers: photoinduced conformational changes and effect of polymeric matrix on the isomerization of photochromes. Die Makromol Chem 182(11):3223–3236 CrossRef
- Yager KG, Barrett CJ (2006) Photomechanical surface patterning in azo-polymer materials. Macromolecules 39(26):9320–9326 CrossRef
- Kim HK, Wang XS, Fujita Y, Sudo A, Nishida H, Fujii M, Endo T (2005) Photomechanical switching behavior of semi-interpenetrating polymer network consisting of azobenzene-carrying crosslinked poly(vinyl ether) and polycarbonate. Macromol Rapid Commun 26(13):1032–1036 CrossRef
- Kim HK, Wang XS, Fujita Y, Sudo A, Nishida H, Fujii M, Endo T (2005) A rapid photomechanical switching polymer blend system composed of azobenzene-carrying poly(vinylether) and poly(carbonate). Polymer 46(16):5879–5883 CrossRef
- Kim HK, Wang XS, Fujita Y, Sudo A, Nishida H, Fujii M, Endo T (2005) Reversible photo-mechanical switching behavior of azobenzene-containing semi-interpenetrating network under UV and visible light irradiation. Macromol Chem Phys 206(20):2106–2111 CrossRef
- Tanaka S, Kim HK, Sudo A, Nishida H, Endo T (2008) Anisotropic photomechanical response of stretched blend film made of polycaprolactone-polyvinyl ether with azobenzene group as side chain. Macromol Chem Phys 209(20):2071–2077 CrossRef
- Zhang C, Zhao X, Chao D, Lu X, Chen C, Wang C, Zhang W (2009) Rapid bending of a nonliquid crystal azobenzene polymer film and characteristics of surface relief grating. J Appl Polym Sci 113(2):1330–1334 CrossRef
- Kim HK, Shin W, Ahn TJ (2010) UV sensor based on photomechanically functional polymer-coated FBG. IEEE Photonics Technol Lett 22(19):1404–1406 CrossRef
- Kim KT, Moon NI, Kim HK (2010) A fiber-optic UV sensor based on a side-polished single mode fiber covered with azobenzene dye-doped polycarbonate. Sens Actuators, A 160(1–2):19–21
- Li N, Ye G, He Y, Wang X (2011) Hollow microspheres of amphiphilic azo homopolymers: self-assembly and photoinduced deformation behavior. Chem Commun 47(16):4757–4759 CrossRef
- Liu J, He Y, Wang X (2010) Influence of chromophoric electron-withdrawing groups on photoinduced deformation of azo polymer colloids. Polymer 51(13):2879–2886 CrossRef
- Liu JH, Chiu YH (2010) Behaviors of self-assembled diblock copolymer with pendant photosensitive azobenzene segments. J Polym Sci Part A Pol Chem 48(5):1142–1148 CrossRef
- Liu J, He Y, Wang X (2008) Azo polymer colloidal spheres containing different amounts of functional groups and their photoinduced deformation behavior. Langmuir 24(3):678–682 CrossRef
- Liu J, He Y, Wang X (2009) Size-dependent light-driven effect observed for azo polymer colloidal spheres with different average diameters. Langmuir 25(10):5974–5979 CrossRef
- Küpfer J, Nishikawa E, Finkelmann H (1994) Densely crosslinked liquid single-crystal elastomers. Polym Adv Technol 5(2):110–115 CrossRef
- Wermter H, Finkelmann H (2001) Liquid crystalline elastomers as artificial muscles. e-Polymers 013:1–13
- Gennes PGD, Hebert M, Kant R (1997) Artificial muscles based on nematic gels. Macromol Symp 113:39–49 CrossRef
- Ikeda T, Mamiya J, Yu YL (2007) Photomechanics of liquid-crystalline elastomers and other polymers. Angew Chem Int Ed 46(4):506–528 CrossRef
- Elias AL, Harris KD, Bastiaansen CWM, Broer DJ, Brett MJ (2006) Photopatterned liquid crystalline polymers for microactuators. J Mater Chem 16(28):2903–2912 CrossRef
- Yang H, Ye G, Wang X, Keller P (2011) Micron-sized liquid crystalline elastomer actuators. Soft Matter 7(3):815–823 CrossRef
- Finkelmann H, Nishikawa E, Pereira GG, Warner M (2001) A new opto-mechanical effect in solids. Phys Rev Lett 87(1):015501 CrossRef
- Hogan PM, Tajbakhsh AR, Terentjev EM (2002) uv manipulation of order and macroscopic shape in nematic elastomers. Phys Rev E 65(4):041720 CrossRef
- Cviklinski J, Tajbakhsh AR, Terentjev EM (2002) UV isomerisation in nematic elastomers as a route to photo-mechanical transducer. Eur Phys J E 9(5):427–434 CrossRef
- Li MH, Keller P, Li B, Wang X, Brunet M (2003) Light-driven side-on nematic elastomer actuators. Adv Mater 15(7–8):569–572 CrossRef
- Yu Y, Nakano M, Ikeda T (2004) Photoinduced bending and unbending behavior of liquid-crystalline gels and elastomers. Pure Appl Chem 76(7–8):1467–1477 CrossRef
- Nakano H (2010) Direction control of photomechanical bending of a photochromic molecular fiber. J Mater Chem 20(11):2071–2074 CrossRef
- Yoshino T, Kondo M, Mamiya J, Kinoshita M, Yu YL, Ikeda T (2010) Three-dimensional photomobility of crosslinked azobenzene liquid-crystalline polymer fibers. Adv Mater 22(12):1361–1363 CrossRef
- Kondo M, Yu Y, Ikeda T (2006) How does the initial alignment of mesogens affect the photoinduced bending behavior of liquid-crystalline elastomers? Angew Chem Int Ed 45(9):1378–1382 CrossRef
- Tabiryan N, Serak S, Dai XM, Bunning T (2005) Polymer film with optically controlled form and actuation. Opt Express 13(19):7442–7448 CrossRef
- Van Oosten CL, Corbett D, Davies D, Warner M, Bastiaansen CWM, Broer DJ (2008) Bending dynamics and directionality reversal in liquid crystal network photoactuators. Macromolecules 41(22):8592–8596 CrossRef
- Priimagi A, Shimamura A, Kondo M, Hiraoka T, Kubo S, Mamiya J, Kinoshita M, Ikeda T, Shishido A (2012) Location of the azobenzene moieties within the cross-linked liquid-crystalline polymers can dictate the direction of photoinduced bending. ACS Macro Lett 1(1):96–99. doi:10.1021/mz200056w CrossRef
- Harris KD, Cuypers R, Scheibe P, van Oosten CL, Bastiaansen CWM, Lub J, Broer DJ (2005) Large amplitude light-induced motion in high elastic modulus polymer actuators. J Mater Chem 15(47):5043–5048 CrossRef
- Kondo M, Sugimoto M, Yamada M, Naka Y, Mamiya JI, Kinoshita M, Shishido A, Yu Y, Ikeda T (2010) Effect of concentration of photoactive chromophores on photomechanical properties of crosslinked azobenzene liquid-crystalline polymers. J Mater Chem 20(1):117–122 CrossRef
- Lee KM, Koerner H, Vaia RA, Bunning TJ, White TJ (2010) Relationship between the photomechanical response and the thermomechanical properties of azobenzene liquid crystalline polymer networks. Macromolecules 43(19):8185–8190 CrossRef
- Shimamura A, Priimagi A, Mamiya J, Ikeda T, Yu Y, Barrett CJ, Shishido A (2011) Simultaneous analysis of optical and mechanical properties of cross-linked azobenzene-containing liquid-crystalline polymer films. ACS Appl Mater Interfaces 3(11):4190–4196 CrossRef
- Bar-Cohen Y (ed) (2004) Electroactive polymer (EAP) actuators as artificial muscles: reality, potential, and challenges, 2nd edn. SPIE Press, Bellingham
- Mirfakhrai T, Madden JDW, Baughman RH (2007) Polymer artificial muscles. Mater Today 10(4):30–38 CrossRef
- Yamada M, Kondo M, Miyasato R, Naka Y, Mamiya JI, Kinoshita M, Shishido A, Yu Y, Barrett CJ, Ikeda T (2009) Photomobile polymer materials—various three-dimensional movements. J Mater Chem 19(1):60–62 CrossRef
- Naka Y, Mamiya J-i, Shishido A, Washio M, Ikeda T (2011) Direct fabrication of photomobile polymer materials with an adhesive-free bilayer structure by electron-beam irradiation. J Mater Chem 21(6):1681–1683 CrossRef
- Yin RY, Xu WX, Kondo M, Yen CC, Mamiya J, Ikeda T, Yu YL (2009) Can sunlight drive the photoinduced bending of polymer films? J Mater Chem 19(20):3141–3143 CrossRef
- Cheng F, Yin R, Zhang Y, Yen CC, Yu Y (2010) Fully plastic microrobots which manipulate objects using only visible light. Soft Matter 6(15):3447–3449 CrossRef
- Cheng F, Zhang Y, Yin R, Yu Y (2010) Visible light induced bending and unbending behavior of crosslinked liquid-crystalline polymer films containing azotolane moieties. J Mater Chem 20(23):4888–4896 CrossRef
- Lee KM, Koerner H, Vaia RA, Bunning TJ, White TJ (2011) Light-activated shape memory of glassy, azobenzene liquid crystalline polymer networks. Soft Matter 7(9):4318–4324 CrossRef
- Wu W, Yao L, Yang T, Yin R, Li F, Yu Y (2011) NIR-light-induced deformation of cross-linked liquid-crystal polymers using upconversion nanophosphors. J Am Chem Soc 133(40):15810–15813 CrossRef
- Chen M, Xing X, Liu Z, Zhu Y, Liu H, Yu Y, Cheng F (2010) Photodeformable polymer material: towards light-driven micropump applications. Appl Phys A Mater Sci Proc 100(1):39–43 CrossRef
- Liu H, Zhu Y, Liu Z, Chen M (2010) Research of photo-induced bending thin film microactuators. Yadian Yu Shengguang/Piezoelectrics and Acoustooptics 32(3):417–419
- van Oosten CL, Bastiaansen CWM, Broer DJ (2009) Printed artificial cilia from liquid-crystal network actuators modularly driven by light. Nat Mater 8(8):677–682 CrossRef
- Palffy-Muhoray P (2009) Liquid crystals: printed actuators in a flap. Nat Mater 8(8):614–615 CrossRef
- Toda F (ed) (2002) Organic solid state reactions. Kluwer, Drodrecht
- Tanaka K, Toda F (2000) Solvent-free organic synthesis. Chem Rev 100(3):1025–1074 CrossRef
- Kaupp G (1992) Photodimerization of cinnamic acid in the solid state: new insights on application of atomic force microscopy. Angew Chem Int Ed 31(5):592–595 CrossRef
- Kaupp G (1992) Photodimerization of anthracenes in the solid state: new results from atomic force microscopy. Angew Chem Int Ed 31(5):595–598 CrossRef
- Irie M, Kobatake S, Horichi M (2001) Reversible surface morphology changes of a photochromic diarylethene single crystal by photoirradiation. Science 291(5509):1769–1772 CrossRef
- Koshima H, Ide Y, Ojima N (2008) Surface morphology changes of a salt crystal of 4-(2,5-diisopropylbenzoyl)benzoic acid with (S)-phenylethylamine via single-crystal-to-single-crystal photocyclization. Cryst Growth Des 8(7):2058–2060 CrossRef
- Kobatake S, Takami S, Muto H, Ishikawa T, Irie M (2007) Rapid and reversible shape changes of molecular crystals on photoirradiation. Nature 446(7137):778–781 CrossRef
- Morimoto M, Irie M (2010) A diarylethene cocrystal that converts light into mechanical work. J Am Chem Soc 132(40):14172–14178 CrossRef
- Nakayama K, Jiang L, Iyoda T, Hashimoto K, Fujishima A (1997) Photo-induced structural transformation on the surface of azobenzene crystals. Jpn J Appl Phys 36:3898–3902 CrossRef
- Ichimura K (2009) Reversible photoisomerisability and particle size changes of mill-dispersed azobenzene crystals in water. Chem Commun 12:1496–1498 CrossRef
- Ichimura K (2010) Photoisomerisation behaviour of azobenzene crystals hybridised with silica nanoparticles by dry grinding. Chem Commun 46(19):3295–3297 CrossRef
- Nakano H, Tanino T, Shirota Y (2005) Surface relief grating formation on a single crystal of 4-(dimethylamino)azobenzene. Appl Phys Lett 87(6):061910 CrossRef
- Nakano H (2008) Photoinduced surface relief grating formation on a (100) surface of a single crystal of 4-(dimethylamino)azobenzene. J Phys Chem C 112(41):16042–16045 CrossRef
- Nakano H (2010) Photoinduced surface relief grating formation for a single crystal of 4-aminoazobenzene. Int J Mol Sci 11(4):1311–1320 CrossRef
- Nakano H, Seki S, Kageyama H (2010) Photoinduced vitrification near the surfaces of single crystals of azobenzene-based molecular materials with glass-forming ability. Phys Chem Chem Phys 12(28):7772–7774 CrossRef
- Koshima H, Ojima N, Uchimoto H (2009) Mechanical motion of azobenzene crystals upon photoirradiation. J Am Chem Soc 131(20):6890–6891 CrossRef
- Milam K, O’Malley G, Kim N, Golovaty D, Kyu T (2010) Swimming photochromic azobenzene single crystals in triacrylate solution. J Phys Chem B 114(23):7791–7796 CrossRef
About this Article
- Title
- Azobenzene photomechanics: prospects and potential applications
- Journal
-
Polymer Bulletin
Volume 69, Issue 8 , pp 967-1006 - Cover Date
- 2012-11-01
- DOI
- 10.1007/s00289-012-0792-0
- Print ISSN
- 0170-0839
- Online ISSN
- 1436-2449
- Publisher
- Springer-Verlag
- Additional Links
- Topics
- Keywords
-
- Azobenzene
- Photomechanics
- Thin films
- Light harvesting
- Liquid crystals
- Photochemistry
- Industry Sectors
- Authors
-
- Zahid Mahimwalla (1)
- Kevin G. Yager (2)
- Jun-ichi Mamiya (3)
- Atsushi Shishido (3)
- Arri Priimagi (3) (4)
-
Christopher J. Barrett
(1)
- Author Affiliations
-
- 1. Department of Chemistry, McGill University, Montreal, Canada
- 2. Center for Functional Nanomaterials, Brookhaven National Laboratory, Upton, NY, USA
- 3. Chemical Resources Laboratory, Tokyo Institute of Technology, Yokohama, Japan
- 4. Department of Applied Physics, Aalto University, Aalto, Finland