Alkynyl-Containing Discotic Liquid Crystal Molecules
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Published
Aug 28, 2022
Abstract
Under specific circumstances, organized columnar phases can be formed from the planar discoid shapes of the molecules that make up discotic liquid crystals. These materials offer unusual features because of their distinct columnar phase structure. They are utilized in organic semiconductors, liquid crystal magnetic materials, and photoelectric conversion. It has numerous applications, so researchers are paying more and more attention to it. In this paper, the effects of alkynyl groups on the properties of discotic liquid crystals at various positions are emphatically discussed. The main focus is on the alkynyl-containing discotic liquid crystal molecules and their properties reported in domestic and foreign literature in the past ten years.
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Keywords
Discotic Liquid Crystal, Alkynyl Group, Organic Semiconductor, Polymers
References
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13. Varshney SK, Takezoe H, Rao DS. Discotic liquid crystals: Synthesis and characterization of radial polyalkynylbenzene derivatives. Bull Chem Soc Japan 2008; 81(1):163-167. DOI: https://doi.org/10.1246/bcsj.81.163
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16. Ryu MH, Choi JW, Cho BK. Design synthesis and self-assembly behavior of C3-symmetry discotic molecules via click chemistry. J Mat Chem 2010; 20(9):1806-1810. DOI: https://doi.org/10.1039/b921685e
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19. Li T, Yue K, Yan Q, Huang H, Wu H, Zhu N, Zhao D. Triangular arylene ethynylene macrocycles: Syntheses, optical, and thermotropic liquid crystalline properties. Soft Mat 2012; 8(8):2405-2415. DOI: https://doi.org/10.1039/c2sm06144a
20. Fritzsche M, Bohle A, Dudenko D, Baumeister U, Sebastiani D, Richardt G, Spiess HW, Hansen MR, Höger S. Empty helical nanochannels with adjustable order from low symmetry macrocycles. Angewandte Chem Int Ed 2011; 50(13):3030-3033. DOI: https://doi.org/10.1002/anie.201007437
21. Luo J, Yan Q, Zhou Y, Li T, Zhu N, Bai C, Cao Y, Wang J, Pei J, Zhao D. A photoswitch based on self-assembled single microwire of a phenyleneethynylene macrocycle. Chem Comm 2010; 46(31):5725-5727. DOI: https://doi.org/10.1039/c0cc00739k
22. Kato S, Takahashi N, Tanaka H, Kobayashi A, Yoshihara T, Tobita S, Yamanobe T, Uehara H, Nakamura Y. Tetraalkoxyphenanthrene-fused dehydroannulenes: Synthesis, self-assembly, and electronic, optical, and electrochemical properties. Chem Eur J 2013; 19(36):12138-12151. DOI: https://doi.org/10.1002/chem.201301262
23. Andrew NC, Hemant G. Synthesis and liquid crystal properties of mixed alkynyl-alkoxy-triphenylenes. Liq Cryst 2009; 36(8):809-816. DOI: https://doi.org/10.1080/02678290903063000
24. Wang D, Mi YS, Tang JK, Liang PX, Jin ZK, Yang Z, Yang H. Disk-shaped symmetric hexa-substituted triphenylene derivatives: Synthesis, physical properties and self-assembly. Chem Res Chin Univ 2013; 29(3):495-499. DOI: https://doi.org/10.1007/s40242-013-2288-3
25. Zhao KQ, Zhou H, Yu W H, Hu P, Wang BQ, Monobe H, Shimizu Y. Synthesis of functionalized triphenylene discotic liquid crystals and the influence of unsaturated periphery on mesomorphism. Sci Chin (B) 2011; 41(10):1565-1574.
26. Fechtenktter A, Tchebotareva N, Watson M, Müllen K. Discotic liquid crystalline hexabenzocoronenes carrying chiral and racemic branched alkyl chains: Supramolecular engineering and improved synthetic methods. Tetrahedron 2001; 57(17):3769-3774. DOI: https://doi.org/10.1016/S0040-4020(01)00252-6
27. Dössel LF, Kamm V, Howard IA, Laquai F, Pisula W, Feng X, Li C, Takase M, Kudernac T, Feyter S. Synthesis and controlled self-assembly of covalently linked hexaperi-hexabenzo-coronene/perylene diimide dyads as models to study fundamental energy and electron transfer processes. J Am Chem Soc 2012; 134(13):5876-5886. DOI: https://doi.org/10.1021/ja211504a
28. Belviso S, Amati M, Rossano R, Crispini A, Lelj F. Non symmetrical aryl-and arylethynyl-substituted thioalkyl-porphyrazines for optoelectronic materials: Synthesis, properties, and computational studies. Dalton Transact 2015; 44(5):2191-2207. DOI: https://doi.org/10.1039/C4DT03317E
29. Kayal H, Ahmida M, Dufour S, Taing H, Eichhorn SH. Cross-linking of discotic tetraazaporphyrin dyes in 2 and 3 dimensions by "click" chemistry. J Mat Chem C, 2013; 1(42):7064-7072. DOI: https://doi.org/10.1039/c3tc31588f
30. Zhao KQ, Zhou H, Yu W H, Wang BQ, Hu P. Palladium catalyzed homo-coupling reaction for the synthesis of rigid-spacer connected discotic liquid crystal dimers with triphenylene mesogens. Acta Chim Sin 2011; 69(16):1895-1902.
31. Zhao KQ, An LL, Zhang XB, Yu WH, Hu P, Wang BQ, Xu J, Zeng QD, Hirosato M, Yo S, Beno H, Bertrand D. Highly segregated lamello-columnar mesophase organizations and fast charge carrier mobility in new discotic donor-acceptor triads. Chem Eur J 2015; 21(8):10379-10390.
32. Xing CM, Jacky WYL, Zhao KQ, Tang BZ. Synthesis and liquid crystalline properties of poly (1-alkyne)s carrying triphenylene discogens. Polymer Chem 2008; 46(9):2960-2974. DOI: https://doi.org/10.1002/(ISSN)1099-0518
2. Geelhaar T, Griesar K, Reckmann B. 125 Years of liquid crystals-a scientific revolution in the home. Angewandte Chem Int Ed 2013; 52(34):8798-8809. DOI: https://doi.org/10.1002/anie.201301457
3. Bremer M, Kirsch P, Klasen-Memmer M, Tarumi K. The TV in your pocket:development of liquid-crystal materials for the new millennium. Angewandte Chem Int Ed 2013; 52(34):8880-8896. DOI: https://doi.org/10.1002/anie.201300903
4. Kumar S. Design concepts and synthesis of discotic liquid crystals. Handb Liq Cryst 2014; 26(4):467-520.
5. Bushby RJ, Boden N. Responses of discotic liquid crystals to mechanical, magnetic, and electrical fields. Handb Liq Crys 2014; 26(5):569-602.
6. Chen SS, Li T, Zhao DH. Progress in discotic liquid crystalline materials. Acta Physic Chim Sin 2010; 26(4):1124-1134.
7. Monika G, Santanu K P. Triphenylene-based room-temperature discotic liquid crystals: Aa new class of blue-light-emitting materials with long-range columnar self-assembly. Langmuir 2016; 32(4):1120-1126. DOI: https://doi.org/10.1021/acs.langmuir.5b03353
8. Yu ZQ, Lam JWY, Zhao KQ, Zhu CZ, Yang S, Lin JS, Li BS, Liu JH, Chen EQ, Tang BZ. Mesogen jacketed liquid crystalline polyacetylene containing triphenylene discogen:synthesis and phase structure. Polymer Chem 2013; 4(4):996-1005. DOI: https://doi.org/10.1039/C2PY20535A
9. Rego JA, Kumar S, Ringsdorf H. Synthesis and characterization of fluorescent, low-symmetry triphenylene discotic liquid crystals: Tailoring of mesomorphic and optical properties. Chem Mat 1996; 8(7):1402-1409. DOI: https://doi.org/10.1021/cm950582x
10. Axenov KV, Laschat S. Thermotropic ionic liquid crystals. Materials (Basel) 2011; 4(1):206-259. DOI: https://doi.org/10.3390/ma4010206
11. Kumar S, Varshney SK, Chauhan D. A room-temperature discotic nematic liquid crystal. Mol Cryst Liq Cryst 2003; 396(1):241-250. DOI: https://doi.org/10.1080/15421400390213573
12. Hiroaki I, Hidenori F, Nobuo K. Ionic charge-transfer liquid crystals formed by alternating supramolecular copolymerization of liquid π-donors and TCNQ. Front Chem 2021; 9. DOI: https://doi.org/10.3389/fchem.2021.657246
13. Varshney SK, Takezoe H, Rao DS. Discotic liquid crystals: Synthesis and characterization of radial polyalkynylbenzene derivatives. Bull Chem Soc Japan 2008; 81(1):163-167. DOI: https://doi.org/10.1246/bcsj.81.163
14. Lee SL, Lin HA, Lin YH, Chen HH, Liao CT, Lin TL, Chu YC, Hsu HF, Chen C, Lee JJ. Gearing of molecular swirls: Columnar packing of nematogenic hexakis(4-alkoxyphenyl-ethynyl)benzene derivatives. Chem Eur J 2011; 17(3):792-799. DOI: https://doi.org/10.1002/chem.v17.3
15. Hennrich G, Cavero E, Barbera J, Gomez LB, Hanes RE, Talarico M, Golemme A, Serrano JL. Optoelectronic devices based on mesomorphic, highly polarizable 1, 3, 5-trisalkynyl benzenes. Chem Mat 2007; 19(25):6068-6070. DOI: https://doi.org/10.1021/cm702617v
16. Ryu MH, Choi JW, Cho BK. Design synthesis and self-assembly behavior of C3-symmetry discotic molecules via click chemistry. J Mat Chem 2010; 20(9):1806-1810. DOI: https://doi.org/10.1039/b921685e
17. Fischer M, Lieser G, Rapp A, Schnell I, Mamdouh W, Feyter S, Schryver FC, Höger S. Shape-persistent macrocycles with intraannular polar groups: Synthesis, liquid crystallinity, and 2D organization. J Am Chem Soc 2004; 126(1):214-222. DOI: https://doi.org/10.1021/ja038484x
18. Seo SH, Jones TV, Seyler H, Peters JO, Kim TH, Chang JY, Tew GN. Liquid crystalline order from orthophenylene ethynylene macrocycles. J Am Chem Soc 2006; 128(29):9264-9265. DOI: https://doi.org/10.1021/ja060354b
19. Li T, Yue K, Yan Q, Huang H, Wu H, Zhu N, Zhao D. Triangular arylene ethynylene macrocycles: Syntheses, optical, and thermotropic liquid crystalline properties. Soft Mat 2012; 8(8):2405-2415. DOI: https://doi.org/10.1039/c2sm06144a
20. Fritzsche M, Bohle A, Dudenko D, Baumeister U, Sebastiani D, Richardt G, Spiess HW, Hansen MR, Höger S. Empty helical nanochannels with adjustable order from low symmetry macrocycles. Angewandte Chem Int Ed 2011; 50(13):3030-3033. DOI: https://doi.org/10.1002/anie.201007437
21. Luo J, Yan Q, Zhou Y, Li T, Zhu N, Bai C, Cao Y, Wang J, Pei J, Zhao D. A photoswitch based on self-assembled single microwire of a phenyleneethynylene macrocycle. Chem Comm 2010; 46(31):5725-5727. DOI: https://doi.org/10.1039/c0cc00739k
22. Kato S, Takahashi N, Tanaka H, Kobayashi A, Yoshihara T, Tobita S, Yamanobe T, Uehara H, Nakamura Y. Tetraalkoxyphenanthrene-fused dehydroannulenes: Synthesis, self-assembly, and electronic, optical, and electrochemical properties. Chem Eur J 2013; 19(36):12138-12151. DOI: https://doi.org/10.1002/chem.201301262
23. Andrew NC, Hemant G. Synthesis and liquid crystal properties of mixed alkynyl-alkoxy-triphenylenes. Liq Cryst 2009; 36(8):809-816. DOI: https://doi.org/10.1080/02678290903063000
24. Wang D, Mi YS, Tang JK, Liang PX, Jin ZK, Yang Z, Yang H. Disk-shaped symmetric hexa-substituted triphenylene derivatives: Synthesis, physical properties and self-assembly. Chem Res Chin Univ 2013; 29(3):495-499. DOI: https://doi.org/10.1007/s40242-013-2288-3
25. Zhao KQ, Zhou H, Yu W H, Hu P, Wang BQ, Monobe H, Shimizu Y. Synthesis of functionalized triphenylene discotic liquid crystals and the influence of unsaturated periphery on mesomorphism. Sci Chin (B) 2011; 41(10):1565-1574.
26. Fechtenktter A, Tchebotareva N, Watson M, Müllen K. Discotic liquid crystalline hexabenzocoronenes carrying chiral and racemic branched alkyl chains: Supramolecular engineering and improved synthetic methods. Tetrahedron 2001; 57(17):3769-3774. DOI: https://doi.org/10.1016/S0040-4020(01)00252-6
27. Dössel LF, Kamm V, Howard IA, Laquai F, Pisula W, Feng X, Li C, Takase M, Kudernac T, Feyter S. Synthesis and controlled self-assembly of covalently linked hexaperi-hexabenzo-coronene/perylene diimide dyads as models to study fundamental energy and electron transfer processes. J Am Chem Soc 2012; 134(13):5876-5886. DOI: https://doi.org/10.1021/ja211504a
28. Belviso S, Amati M, Rossano R, Crispini A, Lelj F. Non symmetrical aryl-and arylethynyl-substituted thioalkyl-porphyrazines for optoelectronic materials: Synthesis, properties, and computational studies. Dalton Transact 2015; 44(5):2191-2207. DOI: https://doi.org/10.1039/C4DT03317E
29. Kayal H, Ahmida M, Dufour S, Taing H, Eichhorn SH. Cross-linking of discotic tetraazaporphyrin dyes in 2 and 3 dimensions by "click" chemistry. J Mat Chem C, 2013; 1(42):7064-7072. DOI: https://doi.org/10.1039/c3tc31588f
30. Zhao KQ, Zhou H, Yu W H, Wang BQ, Hu P. Palladium catalyzed homo-coupling reaction for the synthesis of rigid-spacer connected discotic liquid crystal dimers with triphenylene mesogens. Acta Chim Sin 2011; 69(16):1895-1902.
31. Zhao KQ, An LL, Zhang XB, Yu WH, Hu P, Wang BQ, Xu J, Zeng QD, Hirosato M, Yo S, Beno H, Bertrand D. Highly segregated lamello-columnar mesophase organizations and fast charge carrier mobility in new discotic donor-acceptor triads. Chem Eur J 2015; 21(8):10379-10390.
32. Xing CM, Jacky WYL, Zhao KQ, Tang BZ. Synthesis and liquid crystalline properties of poly (1-alkyne)s carrying triphenylene discogens. Polymer Chem 2008; 46(9):2960-2974. DOI: https://doi.org/10.1002/(ISSN)1099-0518
How to Cite
Jing, T. (2022). Alkynyl-Containing Discotic Liquid Crystal Molecules. Science Insights, 41(3), 619–624. https://doi.org/10.15354/si.22.re075
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