Abstract
The luminescent liquid crystals (LLCs) are expected to solve the conflicts between the aggregation caused quenching and the requirement of aggregation or self-organization for LCs. Herein, we developed a new strategy of applying aggregation-induced emission (AIE) phenomenon to the molecular design of LCs towards LLCs. In this report, a calamitic liquid crystal based on tolane with AIE characteristics was successfully synthesized and the chemical structure was characterized by 1H, 13C NMR, and matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) high-resolution mass spectra. The fluorescence behavior was studied by fluorescence spectroscopy and the liquid crystal phase behaviors were investigated by differential scanning calorimetry (DSC), polarized optical microscopy (POM). The crystal structure was obtained by X-ray diffraction crystallography with P1 space group. Results demonstrated that the sample was AIE active and the LC phases sequence during cooling was nematic, smectic C and smectic B phase.
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Kato T, Mizoshita N, Kishimoto K. Functional liquid-crystalline assemblies: Self-organized soft materials. Angew Chem Int Ed, 2006, 45: 38–68
Weder C, Sarwa C, Montali A, Bastiaansen C, Smith P. Incorporation of photoluminescent polarizers into liquid crystal displays. Science, 1998, 279: 835–837
Whitehead KS, Grell M, Bradley DDC, Inbasekaran M, Woo EP. Polarized emission from liquid crystal polymers. Synthetic Met, 2000, 111: 181–185
Vijayaraghavan RK, Abraham S, Akiyama H, Furumi S, Tamaoki N, Das S. Photoresponsive glass-forming butadiene-based chiral liquid crystals with circularly polarized photoluminescence. Adv Funct Mater, 2008, 18: 2510–2517
Grell M, Bradley DDC. Polarized luminescence from oriented molecular materials. Adv Mater, 1999, 11: 895–905
Chen SH, Shi H, Conger BM, Mastrangelo JC, Tsutsui T. Novel vitrifiable liquid crystals as optical materials. Adv Mater, 1996, 8: 998–1001
Wang H, Zhang F, Bai B, Zhang P, Shi J, Yu D, Zhao Y, Wang Y, Li M. Synthesis, liquid crystalline properties and fluorescence of polycatenar 1,3,4-oxadiazole derivatives. Liq Cryst, 2008, 35: 905–912
Jenekhe SA, Osaheni JA. Excimers and exciplexes of conjugated polymers. Science, 1994, 265: 765–768
Ting CH, Chen JT, Hsu CS. Synthesis and thermal and photoluminescence properties of liquid crystalline polyacetylenes containing 4-alkanyloxyphenyl trans-4-alkylcyclohexanoate side groups. Macromolecules, 2002, 35: 1180–1189
Luo J, Xie Z, Lam JWY, Cheng L, Chen H, Qiu C, Kwok HS, Zhan X, Liu Y, Zhu D, Tang BZ. Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole. Chem Commun, 2001, 18: 1740–1741
Hong Y, Lam JWY, Tang BZ. Aggregation-induced emission: Phenomenon, mechanism and applications. Chem Commun, 2009, (29): 4332–4353
Hong Y, Lam JWY, Tang BZ. Aggregation-induced emission. Chem Soc Rev, 2011, 40: 5361–5388
Zhao ZJ, Wang Z, Lu P, Chan CYK, Liu D, Lam JWY, Sung HHY, Williams ID, Ma YG, Tang BZ. Structural modulation of solid-state emission of 2,5-bis(trialkylsilylethynyl)-3,4-diphenylsiloles. Angew Chem Int Ed, 2009, 48: 7608–7611
Yuan WZ, Lu P, Chen SJ, Lam JWY, Wang Z, Liu Y, Kowk HS, Ma YG, Tang BZ. Changing the behavior of chromophores from aggregation-caused quenching to aggregation-induced emission: Development of highly efficient light emitters in the solid state. Adv Mater, 2010, 22: 2159–2163
Liu J, Lam JWY, Haeussler M, Qin AJ, Tang BZ. Cobalt-containing hyperbranched poly(silylenearylene)s. J Inorg Organomet Polym Mater, 2009, 19: 133–138
Yuan WZ, Yu ZQ, Tang YH, Lam JWY, Xie N, Lu P, Chen EQ, Tang BZ. High solid-state efficiency fluorescent main chain liquid crystalline polytriazoles with aggregation-induced emission characteristics. Macromolecules, 2011, 44: 9618–9628
Li HK, Mei J, Wang J, Zhang S, Zhao QL, Wei Q, Qin AJ, Sun JZ, Tang BZ. Facile synthesis of poly(aroxycarbonyltriazole)s with aggregation-induced emission characteristics by metal-free click polymerization. Sci China Chem, 2011, 54: 611–616
Qin AJ, Zhang Y, Han N, Mei J, Sun JZ, Fan WM, Tang BZ. Preparation and self-assembly of amphiphilic polymer with aggregation-induced emission characteristics. Sci China Chem, 2012, 55: 772–778
Yu Y, Hong YN, Feng C, Liu JZ, Lam JWY, Faisal MT, Ng KM, Luo KQ, Tang, BZ. Synthesis of an AIE-active fluorogen and its application in cell imaging. Sci China Ser B-Chem, 2009, 52: 15–19
Liu Y, Deng CM, Tang L, Qin A, Hu R, Sun JZ, Tang BZ. Specific detection of D-glucose by a tetraphenylethene-based fluorescent sensor. J Am Chem Soc, 2011, 133: 660–663
Tang L, Jin JK, Zhang S, Mao Y, Sun JZ, Yuan WZ, Zhao H, Xu HP, Qin AJ, Tang BZ. Detection of the critical micelle concentration of cationic and anionic surfactants based on aggregation-induced emission property of hexaphenylsilole derivatives. Sci China Ser B-Chem, 2009, 52: 755–759
Yuan WZ, Yu ZQ, Lu P, Deng CM, Lam JWY, Wang ZM, Chen EQ, Ma YG, Tang BZ. High efficiency luminescent liquid crystal: Aggregation-induced emission strategy and biaxially oriented mesomorphic structure. J Mater Chem, 2012, 22: 3323–3326
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Chen, Y., Lin, J., Yuan, W. et al. 1-((12-Bromododecyl)oxy)-4-((4-(4-pentylcyclohexyl)phenyl)ethynyl) benzene: Liquid crystal with aggregation-induced emission characteristics. Sci. China Chem. 56, 1191–1196 (2013). https://doi.org/10.1007/s11426-013-4950-5
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DOI: https://doi.org/10.1007/s11426-013-4950-5