Abstract
A fluorophore-photochrome system incorporating an aryleneimine type fluorophore and an azobismaleimide photochrome was developed and the photochemical properties of this system were investigated. The photoisomerization of trans-azoaromatic chromophore leads to the increase of the fluorescence intensity of fluorophore. The cis azobismaleimide isomers revert photochemically to the trans form and the emission intensity decreases. The fluorescence intensity of the imine fluorophore can be modulated under irradiation with UV and visible (436 nm) light due to reversible trans-cis-trans photoisomerization of azobismaleimide partner. The photoisomerization kinetics was obeyed a first-order relationship with a rate constant of 1.95 × 10−2 s−1 for azobismaleimide/imine fluorophore system and for polyazothioetherimide/imine derivative the kinetics was described by a biexponential equation.
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Russew MM, Hecht S (2010) Photoswitches: from molecules to materials. Adv Mater 22:3348–3360
Liu LH, Nakatani K, Ishow E (2009) Synthesis and photophysical properties of a highly fluorescent azo derivative. New J Chem 33:1402–1408
Ercole F, Davis TP, Evans RA (2010) Photo-responsive systems and biomaterials: photochromic polymers, light-triggered self-assembly, surface modification, fluorescence modulation and beyond. Polym Chem 1:37–54
Yildiz I, Deniz E, Raymo FM (2009) Fluorescence modulation with photochromic switches in nanostructured constructs. Chem Soc Rev 38:1859–1867
Berkovic G, Kongrauz V, Weiss V (2000) Spiropyrans and spirooxazines for memories and switches. Chem Rev 100:1741–1754
Evans SD, Johnson SR, Ringsdorf H, Williams LM, Wolf H (1998) Photoswitching of azobenzene derivatives formed on planar and colloidal gold surfaces. Langmuir 14:6436–6440
Wang S, Qi Q, Li C, Ding G, Kim SM (2011) Organic dyes incorporating low-band-gap chromophores based on p-extended benzothiadiazole for dye-sensitized solar cells. Dyes Pigm 89:188–192
Feringa BL (2001) Molecular switches. Wiley-VCH, Weinheim
Raymo FM, Tomasulo M (2005) Electron and energy transfer modulation with photochromic switches. Chem Soc Rev 34:327–336
Tian H, Yang SJ (2004) Recent progresses on diarylethene based photochromic switches. Chem Soc Rev 33:85–97
Chen Y, Xie N (2005) Modulation of a fluorescent switch based on a controllable photochromic diarylethene shutter. J Mater Chem 15:3229–3232
Piard J, Metivier R, Giraud M, Leaustic A, Yu P, Nakatani K (2009) Photoswitching in diarylethene nanoparticles, a trade-off between bulk solid and solution: towards balanced photochromic and fluorescent properties. New J Chem 33:1420–1426
Metivier R, Badre S, Meallet-Renault R, Yu P, Pansu RB, Nakatani K (2009) Fluorescence photoswitching in polymer matrix: mutual influence between photochromic and fluorescent molecules by energy transfer processes. J Phys Chem C 113:11916–11926
Folling MJ, Polyakova S, Belov V, Blaadern A, Rossi ML, Hell SW (2008) Synthesis and characterization of photoswitchable fluorescent silica nanoparticles. Small 4:134–142
Sheepwash MAL, Mitchell RH, Bohne C (2002) Mechanistic insights into the photochromism of trans-10b,10c-dimethyl-10b,10c-dihydropyrene derivatives. J Am Chem Soc 124:4693–4700
Chen L, Wang G, Zhao X (2011) A fluorescence switch based on a controllable photochromic naphthopyran group. J Luminesc 131:1617–1620
Tomasulo M, Giordani S, Raymo FM (2005) Fluorescence modulation in polymer bilayers containing fluorescent and photochromic dopants. Adv Funct Mater 15:787–794
Lewis SM, Harbron EJ (2007) Photomodulated PPV emission in a photochromic polymer film. J Phys Chem C 111:4425–4430
Kumar G, Neckers D (1989) Photochemistry of azobenzene-containing polymers. Chem Rev 89:1915–1925
Rau H (1990) Photoisomerization of azobenzenes. In: Rabek JF (ed) Photochemistry and photophysics, vol. 2. CRC Press, Boca Raton, pp 119–141
Deniz E, Tomasulo M, Cusido J, Sortino S, Raymo FM (2011) Fast and stable photochromic oxazines for fluorescence switching. Langmuir 27:11773–11783
Airinei A, Fifere N, Homocianu M, Gaina C, Gaina V, Simionescu BC (2011) Optical properties of some new azo photoisomerizable bismaleimide derivatives. Int J Mol Sci 12:6176–6193
Airinei A, Homocianu M, Fifere N, Gaina C, Gaina V (2011) Optical properties of some bismaleimide derivatives. Optoelectr Adv Mater—Rapid Commun 5:655–660
Fifere N, Airinei A, Gaina C, Gaina V, Grigoras M, Simionescu BC (2012) Isomerization characteristics of some azobismaleimides. Rev Roum Chim 57:599–607
Dix LR, Ebdon JR, Flint NJ, O’Dell R (1995) Chain extension and crosslinking of telechelic oligomers I. Michael additions of bisamines to bismaleimides and bis(acetylene ketone)s. Eur Polym J 31:647–652
Grigoras M, Cianga I, Farcas A, Nastase G, Ivanoiu M (2000) Fully conjugated and soluble polyazomethines containing 1,1′-binaphtyl groups. Rev Roum Chim 45:703–708
Grigoras M, Catanescu CO, Colotin G (2001) Poly(Schiff base)s containing 1,1′-binaphthyl moieties: synthesis and characterization. Macromol Chem Phys 202:2262–2266
Ding F, Zhao G, Chen S, Liu F, Zhang L (2009) Chloramphenicol binding to human serum albumin: determination of binding constants and binding sites by steady-state fluorescence. J Mol Struct 929:159–166
Gayen A, Chatterjee C, Mukhopadhyay C (2008) GM1-induced structural changes of bovine serum albumin after chemical and thermal disruption of the secondary structure: a Spectroscopic comparison. Biomacromolecules 9:974–983
Lakowicz JR (2006) Principles of fluorescence spectroscopy, 3rd edn. Springer, New York
Grimes AF, Call SE, Vicente DA, English DE, Harbron EJ (2006) Toward efficient photomodulation of conjugated polymer emission: optimizing differential energy transfer in azobenzene-substituted PPV derivatives. J Phys Chem B 110:19183–19190
Smitha P, Asha SK (2007) Structure control for fine tuning fluorescence emission from side-chain azobenzene polymers. J Phys Chem B 111:6364–6373
Shen YQ, Rau H (1991) The environmentally controlled photoisomerization of probe molecules containing azobenzene moieties in solid poly(methyl methacrylate). Makromol Chem 192:945–957
Ruslim C, Ichimura K (1999) Comparative studies on isomerization behavior and photocontrol of nematic liquid crystals using polymethacrylates with 3,3′- and 4,4′-dihexyloxyazobenzenes in side chains. Macromolecules 32:4254–4263
Malkin S, Fischer E (1962) Temperature dependence of photoisomerisation. II. Quantum yields of cis-trans isomerization in azo-compounds. J Phys Chem 66:2482–2486
Zimmerman G, Chow LY, Paik UJ (1958) The photochemical isomerization of azobenzene. J Am Chem Soc 80:3528–3531
Fifere N, Airinei A, Homocianu M, Gaina C, Gaina V, Simionescu BC (2012) Effect of trans-cis photoisomerisation of azobismaleimide derivatives on the emission intensity of an aryleneimine fluorophore. Rev Roum Chim 57:609–614
Suzuki I, Ishizaki T, Hoshi T, Anzai J (2002) Fully reversible isomerization of azobenzene chromophores in polyelectrolyte layered assemblies. Macromolecules 35:577–580
Abdallah D, Whelan J, Dust JM, Hoz S, Buncel E (2009) Energy transfer in the azobenzene-naphthalene light harvesting system. J Phys Chem A 113:6640–6647
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Financial support from the European Union’s Seventh Framework Programme (FP7/2007-2013) under grant agreement n° 264115—STREAM is gratefully acknowledged.
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Fifere, N., Airinei, A., Gaina, C. et al. Fluorescence Modulation and Photochromism in Azobismaleimide Derivatives. J Fluoresc 24, 345–353 (2014). https://doi.org/10.1007/s10895-013-1299-2
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DOI: https://doi.org/10.1007/s10895-013-1299-2