Abstract
A new gelator 1 based on tetraphenylethylene (TPE) and diphenylalanine was designed and synthesized. Compound 1 was non-emissive in solution, but its fluorescence turned on after the formation of gels, due to the aggregation-induced emission (AIE) feature of TPE. Interestingly, the fluorescence was reversibly switched “on-off” upon the “gel-sol” transition. Scanning electron microscope (SEM), confocal laser scanning microscope (CLSM) and X-ray diffraction (XRD) were employed to study the gels.
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Terech P, Weiss R G. Low molecular mass gelators of organic liquids and the properties of their gels. Chem Rev, 1997, 97: 3133–3160
Yang X Y, Zhang G X, Zhang D Q. Stimuli responsive gels based on low molecular weight gelators. J Mater Chem, 2012, 22: 38–50
Žinić M, Vögtle F, Fages F. Cholesterol-based gelators. Top Curr Chem, 2005, 256: 39–76
Wang C, Chen Q, Sun F, et al. Multistimuli responsive organogels based on a new gelator featuring tetrathiafulvalene and azobenzene groups: Reversible tuning of the gel-sol transition by redox reactions and light irradiation. J Am Chem Soc, 2010, 132: 3092–3096
Chen Q, Zhang D Q, Zhang G X, et al. New cholesterol-based gelators with maleimide unit and the relevant michael adducts: Chemoresponsive organogels. Langumir, 2009, 25: 11436–11441
Fages F, Vögtle F, Žinić M. Systematic design of amide- and urea-type gelators with tailored properties. Top Curr Chem, 2005, 256: 77–131
Wang C, Zhang D Q, Zhu D B. A Low-molecular-mass gelator with an electroactive tetrathiafulvalene group: Tuning the gel formation by charge-transfer interaction and oxidation. J Am Chem Soc, 2005, 127: 16372–16373
Yang X Y, Zhang G X, Zhang D Q, et al. A new ex-TTF-based organogelator: Formation of organogels and tuning with fullerene. Langmuir, 2010, 26: 11720–11725
Wang M, Zhang D Q, Zhang G X, et al. Fluorescence enhancement upon gelation and thermally-driven fluorescence switches based on tetraphenylsilole-based organic gelators. Chem Phys Lett, 2009, 475: 64–67
Araki K, Yoshikawa I. Nucleobase-containing gelators. Top Curr Chem, 2005, 256: 133–165
Gronwald O, Shinkai S. Sugar-integrated gelators of organic solvents. Chem Eur J, 2001, 7: 4328–4334
Jung J H, Shinkai S, Shimizu T. Preparation of mesoscale and macroscale silica nanotubes using a sugar-appended azonaphthol gelator assembly. Nano Lett, 2002, 2: 17–20
Kobayashi H, Friggeri A, Koumoto K, et al. Molecular design of “super” hydrogelators: Understanding the gelation process of azobenzene-based sugar derivatives in water. Org Lett, 2002, 4: 1423–1426
Smith A M, Williams R J, Tang C, et al. Fmoc-diphenylalanine self assembles to a hydrogel via a novel architecture based on π-π interlocked β-sheets. Adv Mater, 2008, 20: 37–41
Li X M, Li J Y, Gao Y, et al. Molecular nanofibers of olsalazine form supramolecular hydrogels for reductive release of an anti-inflammatory agent. J Am Chem Soc, 2010, 132: 17707–17709
Yang Z M, Liang G L, Xu B. Enzymatic hydrogelation of small molecules. Acc Chem Res, 2008, 41: 315–326
Yang Z M, Liang G L, Ma M L, et al. Conjugates of naphthalene and dipeptides produce molecular hydrogelators with high efficiency of hydrogelation and superhelical nanofibers. J Mater Chem, 2007, 17: 850–854
Gao P, Zhan C L, Liu L Z, et al. Inter- and intra-molecular H-bonds induced different nanostructures from a multi-H-bonding (MHB) amphiphile: Nanofibers and nanodisks. Chem Commun, 2004, 1174-1175
Zhan C L, Gao P, Liu M H. Self-assembled helical spherical-nanotubes from an L-glutamic acid based bolaamphiphilic low molecular mass organogelator. Chem Commun, 2005, 462-464
Gao P, Zhan C L, Liu M H. Controlled synthesis of double- and multiwall silver nanotubes with template organogel from a bolaamphiphile. Langumir, 2006, 22: 775–779
Jayawarna V, Ali M, Jowitt T A, et al. Nanostructured hydrogels for three-dimensional cell culture through self-assembly of fluorenylmethoxycarbonyl-dipeptides. Adv Mater, 2006, 18: 611–614
Telodano S, Williams R J, Jayawarna V, et al. Enzyme-triggered self-assembly of peptide hydrogels via reversed hydrolysis. J Am Chem Soc, 2006, 128: 1070–1071
Ajayaghosh A, George S J. First phenylenevinylene based organogels: Self-assembled nanostructures via cooperative hydrogen bonding and π-stacking. J Am Chem Soc, 2001, 123: 5148–5149
Ajayaghosh A, Varghese R, Praveen V K, et al. Evolution of nano- to microsized spherical assemblies of a short oligo(p-phenyleneethnylene) into superstructured organogels. Agew Chem Int Ed, 2006, 45: 3261–3264
Babu S S, Praveen V K, Prasanthkumar S, et al. Self-assembly of oligo(para-phenylenevinylene)s through arene-perfluoroarene interactions: π gels with longitudinally controlled fiber growth and supramo-lecular exciplex-mediated enhanced emission. Chem Eur J, 2008, 14: 9577–9584
Hirst A R, Smith D K. Dendritic gelators. Top Curr Chem, 2005, 256: 237–273
Yang X Y, Zhang G X, Zhang D Q, et al. Self-assembly of a dendron-attached tetrathiafulvalene: Gel formation and modulation in the presence of chloranil and metal ions. Small, 2012, 8: 578–584
Chen Q, Feng Y, Zhang D Q, et al. Light-triggered self-assembly of a spiropyran-functionalized dendron into nano-/micrometer-sized particles and photoresponsive organogel with switchable fluorescence. Adv Funct Mater, 2010, 20: 36–42
Chen Q, Zhang D Q, Zhang G X, et al. Multicolor tunable emission from organogels containing tetraphenylethene, perylenediimide, and spiropyran derivatives. Adv Funct Mater, 2010, 20: 3244–3251
Manna S, Saha A, Nandi A K. A two component thermoreversible hydrogel of riboflavin and melamine: Enhancement of photoluminescence in the gel form. Chem Commun, 2006, 4285-4287
Saha A, Manna S, Nandi A K. Temperature and pH sensitive photoluminescence of riboflavin-methyl cellulose hydrogel: Towards and molecular logic gate behaviour. Soft Matter, 2009, 5: 3992–3996
An B K, Lee D S, Lee J S, et al. Strongly fluorescent organogel system comprising fibrillar self-assembly of a trifluoromethyl-based cyanostilbene derivative. J Am Chem Soc, 2004, 126: 10232–10233
Hong Y N, Lam J W Y, Tang B Z. Aggregation-induced emission. Chem Soc Rev, 2011, 40: 5361–5388
Wang M, Zhang G X, Zhang D Q, et al. Fluorescent bio/chemosensors based on silole and tetraphenylethene luminogens with aggregation-induced emission feature. J Mater Chem, 2010, 20: 1858–1867
Sun F, Zhang G X, Zhang D Q, et al. Aqueous fluorescence turn-on sensor for Zn2+ with a tetraphenylethylene compound. Org Lett, 2011, 13: 6378–6381
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Sun, F., Zhang, G. & Zhang, D. A new gelator based on tetraphenylethylene and diphenylalanine: Gel formation and reversible fluorescence tuning. Chin. Sci. Bull. 57, 4284–4288 (2012). https://doi.org/10.1007/s11434-012-5430-6
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DOI: https://doi.org/10.1007/s11434-012-5430-6