Abstract
Rigid–flexible block molecule (RFBM) is a kind of amphiphilic molecule and roughly comprises both hydrophobic, rigid rod-like segments and hydrophilic, flexible coil-like segments. For example, oligo (p-phenylene) and perylenediimide are employed as the rod segments, whereas poly(ethylene oxide) and poly(propylene oxide) as the flexible chains. This chapter addresses the supramolecular self-assembly of the RFBMs into tubular structures. For example, the self-assembly of perylene diimide-derived amphiphiles, perylene diimide–peptide conjugates, amphiphilic porphyrin, porphrin–C60 amphiphile dyad, amphiphilic carbocyanine dye is discussed in terms of their structural characteristics and potent functions. Moreover, the author describes unique self-assembly behavior of hexa-peri-hexabenzocoronene derivatives that are well-known as one of two-dimensional small-sized graphene molecules. The author also introduces the osmosis-responsive formation of vesicle-encapsulated nanotube structures from thioxanthene-derived amphiphile in the coexistence of an unsaturated phospholipid. Supramolecular self-assembly of rosette-type organic nanotubes from pyrimido pyrimidine derivatives is discussed in terms of functionalization strategy of the rosette nanotubes. In the last part of this chapter, the dynamic morphology switching of nanotube structures self-assembled from bent-shaped aromatic or cyclic aromatic amphiphiles, and nanotube formation from boroxine and trimesic acid derivatives are described in terms of molecular arrangement.
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References
Kim HJ, Kim T, Lee M (2011) Responsive nanostructures from aqueous assembly of rigid-flexible block molecules. Acc Chem Res 44:72–82. https://doi.org/10.1021/ar100111n
Yang WY, Lee E, Lee M (2006) Tubular organization with coiled ribbon from amphiphilic rigid-flexible macrocycle. J Am Chem Soc 128:3484–3485. https://doi.org/10.1021/ja057823e
Ryu JH, Kim HJ, Huang ZG, Lee E, Lee M (2006) Self-assembling molecular dumbbells: From nanohelices to nanocapsules triggered by guest intercalation. Angew Chem Int Ed 45:5304–5307. https://doi.org/10.1002/anie.200600971
Zang L, Che Y, Moore JS (2008) One-dimensional self-assembly of planar π-conjugated molecules: adaptable building blocks for organic nanodevices. Acc Chem Res 41:1596–1608. https://doi.org/10.1021/ar800030w
Ma X, Zhang Y, Zheng Y, Zhang Y, Tao X, Che Y, Zhao J (2015) Highly fluorescent one-handed nanotubes assembled from a chiral asymmetric perylene diimide. Chem Commun 51:4231–4233. https://doi.org/10.1039/c5cc00365b
Yue E, Ma X, Zhang Y, Zhang Y, Duan R, Ji H, Li J, Che Y, Zhao J (2014) Fluorescent bilayer nanocoils assembled from an asymmetric perylene diimide molecule with ultrasensitivity for amine vapors. Chem Commun 50:13596–13599. https://doi.org/10.1039/c4cc06915c
Peng C, Zhang Y, Zhang Y, Hu Y, Che Y, Zhao J (2016) Highly fluorescent nanotubes with tunable diameter and wall thickness self-assembled from asymmetric perylene diimides. Small 12:4363–4369. https://doi.org/10.1002/smll.201601073
Hu Y, Ma X, Zhang Y, Che Y, Zhao J (2016) Detection of amines with fluorescent nanotubes: applications in the assessment of meat spoilage. Acs Sensors 1:22–25. https://doi.org/10.1021/acssensors.5b00040
Tidhar Y, Weissman H, Wolf SG, Gulino A, Rybtchinski B (2011) Pathway-dependent self-assembly of perylene diimide/peptide conjugates in aqueous medium. Chem Eur J 17:6068–6075. https://doi.org/10.1002/chem.201003419
Rodler F, Schade B, Jager CM, Backes S, Hampel F, Bottcher C, Clark T, Hirsch A (2015) Amphiphilic Perylene-Calix[4]arene hybrids: synthesis and tunable self-assembly. J Am Chem Soc 137:3308–3317. https://doi.org/10.1021/ja512048t
Huber V, Sengupta S, Wurthner F (2008) Structure-property relationships for self-assembled zinc chlorin light-harvesting dye aggregates. Chem Eur J 14:7791–7807. https://doi.org/10.1002/chem.200800764
Sengupta S, Ebeling D, Patwardhan S, Zhang X, von Berlepsch H, Bottcher C, Stepanenko V, Uemura S, Hentschel C, Fuchs H, Grozema FC, Siebbeles LDA, Holzwarth AR, Chi L, Wurthner F (2012) Biosupramolecular nanowires from chlorophyll dyes with exceptional charge-transport properties. Angew Chem Int Ed 51:6378–6382. https://doi.org/10.1002/anie.201201961
Patwardhan S, Sengupta S, Siebbeles LDA, Wurthner F, Grozema FC (2012) Efficient charge transport in semisynthetic zinc chlorin dye assemblies. J Am Chem Soc 134:16147–16150. https://doi.org/10.1021/ja3075192
Yamamoto Y (2011) Electroactive nanotubes from π-conjugated discotic molecules. Bull Chem Soc Jpn 84:17–25. https://doi.org/10.1246/bcsj.20100272
Hizume Y, Tashiro K, Charvet R, Yamamoto Y, Saeki A, Seki S, Aida T (2010) Chiroselective assembly of a chiral porphyrin-fullerene dyad: photoconductive nanofiber with a top-class ambipolar charge-carrier mobility. J Am Chem Soc 132:6628–6629. https://doi.org/10.1021/ja1014713
Charvet R, Yamamoto Y, Sasaki T, Kim J, Kato K, Takata M, Saeki A, Seki S, Aida T (2012) Segregated and alternately stacked donor/acceptor nanodomains in tubular morphology tailored with zinc porphyrin–C60 amphiphilic dyads: clear geometrical effects on photoconduction. J Am Chem Soc 134:2524–2527. https://doi.org/10.1021/Ja211334k
Li ZQ, Zhang YM, Chen Y, Liu Y (2014) A supramolecular tubular nanoreactor. Chem Eur J 20:8566–8570. https://doi.org/10.1002/chem.201402612
Didraga C, Pugzlys A, Hania PR, von Berlepsch H, Duppen K, Knoester J (2004) Structure, spectroscopy, and microscopic model of tubular carbocyanine dye aggregates. J Phys Chem B 108:14976–14985. https://doi.org/10.1021/jp048288s
Eisele DM, Berlepsch HV, Bottcher C, Stevenson KJ, Bout DAV, Kirstein S, Rabe JP (2010) Photoinitiated growth of sub-7 nm silver nanowires within a chemically active organic nanotubular template. J Am Chem Soc 132:2104–2105. https://doi.org/10.1021/Ja907373h
Walker EK, Vanden Bout DA, Stevenson KJ (2011) Aqueous electrogenerated chemiluminescence of self-assembled double-walled tubular j-aggregates of amphiphilic cyanine dyes. J Phys Chem C 115:2470–2475. https://doi.org/10.1021/Jp1108015
Wu J, Pisula W, Mullen K (2007) Graphenes as potential material for electronics. Chem Rev 107:718–747. https://doi.org/10.1021/cr068010r
Hill JP, Jin W, Kosaka A, Fukushima T, Ichihara H, Shimomura T, Ito K, Hashizume T, Ishii N, Aida T (2004) Self-assembled hexa-peri-hexabenzocoronene graphitic nanotube. Science 304:1481–1483. https://doi.org/10.1126/science.1097789
Jin W, Yamamoto Y, Fukushima T, Ishii N, Kim J, Kato K, Takata M, Aida T (2008) Systematic studies on structural parameters for nanotubular assembly of hexa-peri-hexabenzocoronenes. J Am Chem Soc 130:9434–9440. https://doi.org/10.1021/Ja801179e
Yamamoto Y, Fukushima T, Suna Y, Ishii N, Saeki A, Seki S, Tagawa S, Taniguchi M, Kawai T, Aida T (2006) Photoconductive coaxial nanotubes of molecularly connected electron donor and acceptor layers. Science 314:1761–1764. https://doi.org/10.1126/science.1134441
Yamamoto Y, Fukushima T, Saeki A, Seki S, Tagawa S, Ishii N, Aida T (2007) Molecular engineering of coaxial donor-acceptor heterojunction by coassembly of two different hexabenzocoronenes: graphitic nanotubes with enhanced photoconducting properties. J Am Chem Soc 129:9276–9277. https://doi.org/10.1021/Ja073577q
Yamamoto Y, Zhang GX, Jin WS, Fukushima T, Ishii N, Saeki A, Seki S, Tagawa S, Minari T, Tsukagoshi K, Aida T (2009) Ambipolar-transporting coaxial nanotubes with a tailored molecular graphene-fullerene heterojunction. Proc Natl Acad Sci USA 106:21051–21056. https://doi.org/10.1073/pnas.0905655106
He YN, Yamamoto Y, Jin WS, Fukushima T, Saeki A, Seki S, Ishii N, Aida T (2010) Hexabenzocoronene graphitic nanotube appended with dithienylethene pendants: photochromism for the modulation of photoconductivity. Adv Mater 22:829–832. https://doi.org/10.1002/adma.200902601
Zhang W, Jin W, Fukushima T, Saeki A, Seki S, Aida T (2011) Supramolecular linear heterojunction composed of graphite-like semiconducting nanotubular segments. Science 334:340–343. https://doi.org/10.1126/science.1210369
Zhang W, Jin W, Fukushima T, Mori T, Aida T (2015) Helix sense-selective supramolecular polymerization seeded by a one-handed helical polymeric assembly. J Am Chem Soc 137:13792–13795. https://doi.org/10.1021/jacs.5b09878
Prasanthkumar S, Zhang W, Jin W, Fukushima T, Aida T (2015) Selective synthesis of single- and multi-walled supramolecular nanotubes by using solvophobic/solvophilic controls: stepwise radial growth via “coil-on-tube” intermediates. Angew Chem Int Ed 54:11168–11172. https://doi.org/10.1002/anie.201505806
Shimizu T, Kogiso M, Masuda M (1996) Vesicle assembly in microtubes. Nature 383:487–488. https://doi.org/10.1038/383487b0
Kogiso M, Ohnishi S, Yase K, Masuda M, Shimizu T (1998) Dicarboxylic oligopeptide bolaamphiphiles: proton-triggered self-assembly of microtubes with loose solid surfaces. Langmuir 14:4978–4986. https://doi.org/10.1021/la9802419
Coleman AC, Beierle JM, Stuart MCA, Macia B, Caroli G, Mika JT, van Dijken DJ, Chen JW, Browne WR, Feringa BL (2011) Light-induced disassembly of self-assembled vesicle-capped nanotubes observed in real time. Nat Nanotechnol 6:547–552. https://doi.org/10.1038/Nnano.2011.120
Erne PM, van Bezouwen LS, Stacko P, van Dtjken DJ, Chen JW, Stuart MCA, Boekema EJ, Feringa BL (2015) Loading of vesicles into soft amphiphilic nanotubes using osmosis. Angew Chem Int Ed 54:15122–15127. https://doi.org/10.1002/anie.201506493
Erne PM, Stacko P, van Dijken DJ, Chen J, Stuart MCA, Feringa B (2016) End-capping of amphiphilic nanotubes with phospholipid vesicles: impact of the phospholipid on the cap formation and vesicle loading under osmotic conditions. Chem Commun 52:11697–11700. https://doi.org/10.1039/c6cc05101d
Saha A, Manna S, Nandi AK (2008) Hierarchical tuning of 1-D macro morphology by changing the composition of a binary hydrogel and its influence on the photoluminescence property. Chem Commun 3732–3734. https://doi.org/10.1039/b805344h
Saha A, Roy B, Esterrani A, Nandi AK (2011) Effect of complementary small molecules on the properties of bicomponent hydrogel of riboflavin. Org Biomol Chem 9:770–776. https://doi.org/10.1039/c0ob00670j
Diaz N, Simon FX, Schmutz M, Rawiso M, Decher G, Jestin J, Mésini PJ (2005) Self-assembled diamide nanotubes in organic solvents. Angew Chem Int Ed 44:3260–3264. https://doi.org/10.1002/anie.200500536
Shimizu T (2018) Self-assembly of discrete organic nanotubes. Bull Chem Soc Jpn 91:623–668. https://doi.org/10.1246/bcsj.20170424
Soler-illia GJD, Sanchez C, Lebeau B, Patarin J (2002) Chemical strategies to design textured materials: From microporous and mesoporous oxides to nanonetworks and hierarchical structures. Chem Rev 102:4093–4138. https://doi.org/10.1021/cr0200062
Simon FX, Khelfallah NS, Schmutz M, Diaz N, Mésini PJ (2007) Formation of helical mesopores in organic polymer matrices. J Am Chem Soc 129:3788–3789. https://doi.org/10.1021/ja067261e
Nguyen TTT, Simon FX, Khelfallah NS, Schmutz M, Mésini PJ (2010) Mesoporous polymeric catalysts synthesized from self-assembled organic nanotubes as templates. J Mater Chem 20:3831–3833. https://doi.org/10.1039/c000534g
Marsh A, Silvestri M, Lehn JM (1996) Self-complementary hydrogen bonding heterocycles designed for the enforced self-assembly into supramolecular macrocycles. Chem Commun 1527–1528. https://doi.org/10.1039/cc9960001527
Fenniri H, Mathivanan P, Vidale K, Sherman D, Wood K, Stwell J (2001) Helical rosette nanotubes: design, self-assembly, and characterization. J Am Chem Soc 123:3854–3855. https://doi.org/10.1021/ja005886l
Beingessner RL, Fan YW, Fenniri H (2016) Molecular and supramolecular chemistry of rosette nanotubes. Rsc Adv 6:75820–75838. https://doi.org/10.1039/c6ra16315g
Fenniri H, Deng BL, Ribbe AE, Hallenga K, Jacob J, Thiyagarajan P (2002) Entropically driven self-assembly of multichannel rosette nanotubes. Proc Natl Acad Sci USA 99:6487–6492. https://doi.org/10.1073/pnas.032527099
Chen YP, Song S, Yan ZM, Fenniri H, Webster TJ (2011) Self-assembled rosette nanotubes encapsulate and slowly release dexamethasone. Int J Nanomedicine 6:1035–1044. https://doi.org/10.2147/Ijn.S18755
Song S, Chen YP, Yan ZM, Fenniri H, Webster TJ (2011) Self-assembled rosette nanotubes for incorporating hydrophobic drugs in physiological environments. Int J Nanomedicine 6:101–107. https://doi.org/10.2147/Ijn.S11957
Fukino T, Joo H, Hisada Y, Obana M, Yamagishi H, Hikima T, Takata M, Fujita N, Aida T (2014) Manipulation of discrete nanostructures by selective modulation of noncovalent forces. Science 344:499–504. https://doi.org/10.1126/science.1252120
Muraoka T, Kinbara K, Aida T (2006) Mechanical twisting of a guest by a photoresponsive host. Nature 440:512–515. https://doi.org/10.1038/nature04635
Obana M, Fukino T, Hikima T, Aida T (2016) Self-sorting in the formation of metal-organic nanotubes: a crucial role of 2D cooperative interactions. J Am Chem Soc 138:9246–9250. https://doi.org/10.1021/jacs.6b04693
Huang Z, Kang SK, Banno M, Yamaguchi T, Lee D, Seok C, Yashima E, Lee M (2012) Pulsating tubules from noncovalent macrocycles. Science 337:1521–1526. https://doi.org/10.1126/science.1224741
Kim JK, Lee E, Lim Y, Lee M (2008) Supramolecular capsules with gated pores from an amphiphilic rod assembly. Angew Chem Int Ed 47:4662–4666. https://doi.org/10.1002/anie.200705863
Wu S, Li Y, Xie SY, Ma C, Lim J, Zhao J, Kim DS, Yang M, Yoon DK, Lee M, Kim SO, Huang Z (2017) Supramolecular nanotubules as a catalytic regulator for palladium cations: applications in selective catalysis. Angew Chem Int Ed 56:11511–11514. https://doi.org/10.1002/anie.201706373
Wang Y, Huang Z, Kim Y, He Y, Lee M (2014) Guest-driven inflation of self-assembled nanofibers through hollow channel formation. J Am Chem Soc 136:16152–16155. https://doi.org/10.1021/ja510182x
Moon KS, Kim HJ, Lee E, Lee M (2007) Self-assembly of T-Shaped aromatic amphiphiles into stimulus-responsive nanofibers. Angew Chem Int Ed 46:6807–6810. https://doi.org/10.1002/anie.200702136
Kim Y, Li H, He Y, Chen X, Ma X, Lee M (2017) Collective helicity switching of a DNA-coat assembly. Nat Nanotechnol 12:551–558. https://doi.org/10.1038/Nnano.2017.42
Kim Y, Kang J, Shen B, Wang Y, He Y, Lee M (2015) Open-closed switching of synthetic tubular pores. Nat Commun 6:8650. https://doi.org/10.1038/ncomms9650
Lutz JF, Weichenhan K, Akdemir O, Hoth A (2007) About the phase transitions in aqueous solutions of thermoresponsive copolymers and hydrogels based on 2-(2-methoxyethoxy)ethyl methacrylate and oligo(ethylene glycol) methacrylate. Macromolecules 40:2503–2508. https://doi.org/10.1021/ma062925q
Zhang X, Bera T, Liang W, Fang J (2011) Longitudinal zipping/unzipping of self-assembled organic tubes. J Phys Chem B 115:14445–14449. https://doi.org/10.1021/Jp2064276
Shen B, He Y, Kim Y, Wang Y, Lee M (2016) Spontaneous capture of carbohydrate guests through folding and zipping of self-assembled ribbons. Angew Chem Int Ed 55:2382–2386. https://doi.org/10.1002/anie.201509190
Matile S, Jentzsch AV, Montenegro J, Fin A (2011) Recent synthetic transport systems. Chem Soc Rev 40:2453–2474. https://doi.org/10.1039/c0cs00209g
Fyles TM (2007) Synthetic ion channels in bilayer membranes. Chem Soc Rev 36:335–347. https://doi.org/10.1039/b603256g
Gong B, Shao Z (2013) Self-assembling organic nanotubes with precisely defined, sub-nanometer pores: formation and mass transport characteristics. Acc Chem Res 46:2856–2866. https://doi.org/10.1021/ar400030e
Yang Y, Feng W, Hu J, Zou SL, Gao RZ, Yamato K, Kline M, Cai Z, Gao Y, Wang Y, Li Y, Yang Y, Yuan L, Zeng XC, Gong B (2011) Strong aggregation and directional assembly of aromatic oligoamide macrocycles. J Am Chem Soc 133:18590–18593. https://doi.org/10.1021/ja208548b
Zhou X, Liu G, Yamato K, Shen Y, Cheng R, Wei X, Bai W, Gao Y, Li H, Liu Y, Liu F, Czajkowsky DM, Wang J, Dabney MJ, Cai Z, Hu J, Bright FV, He L, Zeng XC, Shao Z, Gong B (2012) Self-assembling subnanometer pores with unusual mass-transport properties. Nat Commun 3:949. https://doi.org/10.1038/ncomms1949
Chen YL, Zhu B, Han Y, Bo ZS (2012) Self-assembly of cationic pyrene nanotubes. J Mater Chem 22:4927–4931. https://doi.org/10.1039/c2jm15997j
Bösch CD, Langenegger SM, Häner R (2016) Light-harvesting nanotubes formed by supramolecular assembly of aromatic oligophosphates. Angew Chem Int Ed 55:9961–9964. https://doi.org/10.1002/anie.201604508
Faul CFJ, Antonietti M (2003) Ionic self-assembly: facile synthesis of supramolecular materials. Adv Mater 15:673–683. https://doi.org/10.1002/adma.200300379
Wang Z, Medforth CJ, Shelnutt JA (2004) Porphyrin nanotubes by ionic self-assembly. J Am Chem Soc 126:15954–15955. https://doi.org/10.1021/Ja045068j
van Rossum BJ, Steensgaard DB, Mulder FM, Boender GJ, Schaffner K, Holzwarth AR, de Groot HJM (2001) A refined model of the chlorosomal antennae of the green bacterium Chlorobium tepidum from proton chemical shift constraints obtained with high-field 2-D and 3-D MAS NMR dipolar correlation spectroscopy. Biochemistry 40:1587–1595. https://doi.org/10.1021/bi0017529
Franco R, Jacobsen JL, Wang H, Wang Z, Istvan K, Schore NE, Song Y, Medforth CJ, Shelnutt JA (2010) Molecular organization in self-assembled binary porphyrin nanotubes revealed by resonance Raman spectroscopy. PCCP 12:4072–4077. https://doi.org/10.1039/b926068d
Korich AL, Iovine PM (2010) Boroxine chemistry and applications: a perspective. Dalton Trans 39:1423–1431. https://doi.org/10.1039/b917043j
Ishikawa K, Kameta N, Masuda M, Asakawa M, Shimizu T (2014) Boroxine nanotubes: moisture-sensitive morphological transformation and guest release. Adv Funct Mater 24:603–609. https://doi.org/10.1002/adfm.201302005
Shi N, Yin G, Li H, Han M, Xu Z (2008) Uncommon hexagonal microtubule based gel from a simple trimesic amide. New J Chem 32:2011–2015. https://doi.org/10.1039/b804455d
Shimizu T, Kameta N, Ding W, Masuda M (2016) Supramolecular self-assembly into biofunctional soft nanotubes: from bilayers to monolayers. Langmuir 32:12242–12264. https://doi.org/10.1021/acs.langmuir.6b01632
Cao H, Duan P, Zhu X, Jiang J, Liu M (2012) Self-assembled organic nanotubes through instant gelation and universal capacity for guest molecule encapsulation. Chem Eur J 18:5546–5550. https://doi.org/10.1002/chem.201103654
Sahoo P, Kumar DK, Raghavan SR, Dastidar P (2011) Supramolecular synthons in designing low molecular mass gelling agents: l-amino acid methyl ester cinnamate salts and their anti-solvent-induced instant gelation. Chem Asian J 6:1038–1047. https://doi.org/10.1002/asia.201000560
Mu X, Song W, Zhang Y, Ye K, Zhang H, Wang Y (2010) Controllable self-assembly of n-type semiconductors to microtubes and highly conductive ultralong microwires. Adv Mater 22:4905–4909. https://doi.org/10.1002/adma.201002259
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Shimizu, T. (2021). Rigid–Flexible Block Molecule-Based Nanotubes. In: Smart Soft-Matter Nanotubes. Nanostructure Science and Technology. Springer, Singapore. https://doi.org/10.1007/978-981-16-2685-2_9
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