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1-((12-Bromododecyl)oxy)-4-((4-(4-pentylcyclohexyl)phenyl)ethynyl) benzene: Liquid crystal with aggregation-induced emission characteristics

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  • Special Topic Aggregated-Induced Emission
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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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References

  1. Kato T, Mizoshita N, Kishimoto K. Functional liquid-crystalline assemblies: Self-organized soft materials. Angew Chem Int Ed, 2006, 45: 38–68

    Google Scholar 

  2. Weder C, Sarwa C, Montali A, Bastiaansen C, Smith P. Incorporation of photoluminescent polarizers into liquid crystal displays. Science, 1998, 279: 835–837

    Article  CAS  Google Scholar 

  3. Whitehead KS, Grell M, Bradley DDC, Inbasekaran M, Woo EP. Polarized emission from liquid crystal polymers. Synthetic Met, 2000, 111: 181–185

    Article  Google Scholar 

  4. 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

    Article  CAS  Google Scholar 

  5. Grell M, Bradley DDC. Polarized luminescence from oriented molecular materials. Adv Mater, 1999, 11: 895–905

    Article  CAS  Google Scholar 

  6. Chen SH, Shi H, Conger BM, Mastrangelo JC, Tsutsui T. Novel vitrifiable liquid crystals as optical materials. Adv Mater, 1996, 8: 998–1001

    Article  CAS  Google Scholar 

  7. 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

    Article  CAS  Google Scholar 

  8. Jenekhe SA, Osaheni JA. Excimers and exciplexes of conjugated polymers. Science, 1994, 265: 765–768

    Article  CAS  Google Scholar 

  9. 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

    Article  CAS  Google Scholar 

  10. 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

    Article  Google Scholar 

  11. Hong Y, Lam JWY, Tang BZ. Aggregation-induced emission: Phenomenon, mechanism and applications. Chem Commun, 2009, (29): 4332–4353

    Article  Google Scholar 

  12. Hong Y, Lam JWY, Tang BZ. Aggregation-induced emission. Chem Soc Rev, 2011, 40: 5361–5388

    Article  CAS  Google Scholar 

  13. 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

    Article  CAS  Google Scholar 

  14. 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

    Article  CAS  Google Scholar 

  15. 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

    Article  CAS  Google Scholar 

  16. 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

    Article  CAS  Google Scholar 

  17. 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

    Article  CAS  Google Scholar 

  18. 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

    Article  CAS  Google Scholar 

  19. 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

    Article  CAS  Google Scholar 

  20. 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

    Article  CAS  Google Scholar 

  21. 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

    Article  CAS  Google Scholar 

  22. 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

    Article  CAS  Google Scholar 

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Correspondence to ZhenQiang Yu or Ben Zhong Tang.

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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

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