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Article

Luminescent liquid crystals based on 2,1,3-benzoxadiazole: conducive heterocycle or poor cousin of benzothiadiazole?

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Pages 1707-1717 | Received 26 Dec 2018, Accepted 12 Mar 2019, Published online: 02 Jul 2019

References

  • Bremer M, Kirsch P, Klasen-Memmer M, et al. The TV in your pocket: development of liquid-crystal materials for the new millennium. Angew Chem Int Ed. 2013;52(34):8880–8896.
  • Wöhrle T, Wurzbach I, Kirres J, et al. Discotic liquid crystals. Chem Rev. 2016;116(3):1139–1241.
  • Wang Y, Shi J, Chen J, et al. Recent progress in luminescent liquid crystal materials: design, properties and application for linearly polarised emission. J Mat Chem C. 2015;3(31):7993–8005.
  • Seed AJ, Sampson P. A review of self-organising 2,5- and 2,4-disubstituted 1,3-thiazole-containing materials: synthesis, mechanisms and tactics. Liq Cryst. 2017;44(12–13):1894–1910.
  • Roy B, De N, Majumdar KC. Advances in metal-free heterocycle-based columnar liquid crystals. Chem Eur J. 2012;18(46):14560–14588.
  • Seed A. Synthesis of self-organizing mesogenic materials containing a sulfur-based five-membered heterocyclic core. Chem Soc Rev. 2007;36(12):2046–2069.
  • Ghosh T, Lehmann M. Recent advances in heterocycle-based metal-free calamitics. J Mat Chem C. 2017;5(47):12308–12337.
  • Saha SK, Deb J, Sarkar U, et al. Hockey-stick-shaped mesogens based on 1,3,4-thiadiazole: synthesis, mesomorphism, photophysical and DFT studies. Liq Cryst. 2017;44(14–15):2203–2221.
  • Zhang H, Shiino S, Shishido A, et al. A thiophene liquid crystal as a novel π-conjugated dye for photo-manipulation of molecular alignment. Adv Mater. 2000;12(18):1336–1339.
  • Vera F, Tejedor RM, Romero P, et al. Light-driven supramolecular chirality in propeller-like hydrogen-bonded complexes that show columnar mesomorphism. Angew Chem Int Ed. 2007;46(11):1873–1877.
  • Matharu AS, Jeeva S, Ramanujam PS. Liquid crystals for holographic optical data storage. Chem Soc Rev. 2007;36(12):1868–1880.
  • Liau W-L, Su Y-J, Tseng H-F, et al. Synthesis and characterisation of liquid crystal molecules based on thieno [3,2-b] thiophene and their application in organic field-effect transistors. Liq Cryst. 2017;44(3):557–565.
  • Wang Y, Fan J, Shi J, et al. Influence of integrated alkyl-chain length on the mesogenic and photophysical properties of platinum-based metallomesogens and their application for polarized white OLEDs. Dyes Pigm. 2016;133:238–247.
  • Wang Y, Liao Y, Cabry CP, et al. Highly efficient blueish-green fluorescent OLEDs based on AIE liquid crystal molecules: from ingenious molecular design to multifunction materials. J Mat Chem C. 2017;5(16):3999–4008.
  • Huang D, Prehm M, Gao H, et al. Synthesis and self-assembly of luminescent hexacatenar molecules incorporating a 4,7-diphenyl-2,1,3-benzothiadiazole core. RSC Adv. 2016;6(26):21387–21395.
  • Irie M. Diarylethenes for memories and switches. Chem Rev. 2000;100(5):1685–1716.
  • Yokoyama Y. Molecular switches with photochromic fulgides. In: Feringa BL, editor. Molecular Switches. Vol. 1. Weinheim, Germany: Wiley‐VCH; 2011. p. 81–95.
  • Han J. 1,3,4-Oxadiazole based liquid crystals. J Mat Chem C. 2013;1(47):7779–7797.
  • Parra ML, Elgueta EY, Jimenez V, et al. Novel amides and Schiff’s bases derived from 1,3,4-oxadiazole derivatives: synthesis and mesomorphic behaviour. Liq Cryst. 2009;36(3):301–317.
  • Tomi IHR, Mmar A-O, Al-Daraji AHR. Synthesis, characterisation and mesomorphic behaviours of non-symmetrically substituted 1,2,4- and 1,3,4-oxadiazole derivatives. Liq Cryst. 2017;44(4):603–608.
  • Mmar A-O, Tomi IHR, Jaffer HJ. Non-symmetrically (1,2,4- and 1,3,4-)oxadiazole homologous: synthesis, characterisation and study the effect of different substituents on their mesophase behaviours. Liq Cryst. 2017;44(7):1131–1145.
  • Tuzimoto P, Santos DMPO, TdS M, et al. Luminescent liquid crystals containing a sulphur-based heterocyclic core. Liq Cryst. 2014;41(8):1097–1108.
  • Kuo H-M, Li S-Y, Sheu H-S, et al. Symmetrical mesogenic 2,5-bis(6-naphthalen-2-yl)-1,3,4-thiadiazoles. Tetrahedron. 2012;68(36):7331–7337.
  • Regis E, LdO A, Tuzimoto P, et al. Effect of heteroatom exchange (S/Se) in the mesomorphism and physical properties of benzochalcogenodiazole-based liquid crystals. Dyes Pigm. 2018;157:109–116.
  • Foster EJ, Babuin J, Nguyen N, et al. Synthesis of unsymmetrical dibenzoquinoxaline discotic mesogens. Chem Comm. 2004;(18):2052–2053. DOI:10.1039/B400998C
  • Gupta RK, Pathak SK, De J, et al. Room temperature columnar liquid crystalline self-assembly of acidochromic, luminescent, star-shaped molecules with cyanovinylene chromophores. J Mat Chem C. 2018;6(7):1844–1852.
  • Wei B, Tan S, Liang T, et al. Synthesis, structural and electrochemical characterization of benzimidazole compounds exhibiting a smectic C liquid crystal phase. J Mol Struct. 2017;1133:392–397.
  • Xu Y, Chen X, Zhao F, et al. Synthesis and properties of substituted benzoxazole-terminated liquid crystals. Liq Cryst. 2013;40(2):197–215.
  • Wang C-S, Wang IW, Cheng K-L, et al. The effect of polar substituents on the heterocyclic benzoxazoles. Tetrahedron. 2006;62(40):9383–9392.
  • Hu K, Xu Y, Chen P, et al. Synthesis and characterisation of benzoxazole-based liquid crystals possessing 3,5-difluorophenyl unit. Liq Cryst. 2014;41(10):1455–1464.
  • Weng Q, Duan L, Chen P, et al. Synthesis and mesomorphic properties of benzoxazole derivatives with lateral multifluoro substituents. Liq Cryst. 2019;46(1):59–66.
  • Duan L, Shi D, Chen P, et al. Preparation and properties of laterally multifluorinated benzoxazole-based nematic mesogens. Liq Cryst. 2017;44(11):1686–1694.
  • Struijk CW, Sieval AB, Dakhorst JEJ, et al. Liquid crystalline perylene diimides: architecture and charge carrier mobilities. J Am Chem Soc. 2000;122(45):11057–11066.
  • LdO A, Regis E, Tuzimoto P, et al. Investigation of thermal and luminescent properties in 4,7-diphenylethynyl-2,1,3-benzothiadiazole systems. Liq Cryst. 2018;45(1):49–58.
  • Gallardo H, Conte G, Tuzimoto PA, et al. New luminescent liquid crystals based on 2,1,3-benzothiadiazole and bent five-membered N-heterocyclic cores. Liq Cryst. 2012;39(9):1099–1111.
  • Fang H, Gao H, Wang T, et al. Benzothiadiazole-based D-π-A-π-D fluorophores: synthesis, self-assembly, thermal and photophysical characterization. Dyes Pigm. 2017;147:190–198.
  • Wang B, Pan H, Jia J, et al. Highly emissive dimesitylboryl-substituted 2,1,3-benzothiadiazole derivatives: photophysical properties and efficient fluorescent sensor for fluoride anions. Tetrahedron. 2014;70(35):5488–5493.
  • Pati PB. Benzazole (B, N, O, S, Se and Te) based D-A-D type oligomers: switch from electropolymerization to structural aspect. Org Electron. 2016;38:97–106.
  • Coombs BA, Lindner BD, Edkins RM, et al. Photophysical property trends for a homologous series of bis-ethynyl-substituted benzochalcogendiazoles. New J Chem. 2012;36(3):550–553.
  • Behramand B, Molin F, Gallardo H. 2,1,3-Benzoxadiazole and 2,1,3-benzothiadiazole-based fluorescent compounds: synthesis, characterization and photophysical/electrochemical properties. Dyes Pigm. 2012;95(3):600–605.
  • Bouffard J, Swager TM. Fluorescent conjugated polymers that incorporate substituted 2,1,3-benzooxadiazole and 2,1,3-benzothiadiazole units. Macromolecules. 2008;41(15):5559–5562.
  • Wu G, Zhang Y, Kaneko R, et al. A 2,1,3-benzooxadiazole moiety in a D–A–D-type hole-transporting material for boosting the photovoltage in perovskite solar cells. J Phys Chem C. 2017;121(33):17617–17624.
  • Göker S, Hızalan G, Udum YA, et al. Electrochemical and optical properties of 5,6-bis(octyloxy)-2,1,3 benzooxadiazole containing low band gap polymers. Synth Met. 2014;191:19–27.
  • Uttam B, Kandi R, Hussain MA, et al. Fluorescent lower rim 1,3-dibenzooxadiazole conjugate of calix[4]arene in selective sensing of fluoride in solution and in biological cells using confocal microscopy. J Org Chem. 2018;83(19):11850–11859.
  • Qiu X, Jiao X, Liu C, et al. A selective and sensitive fluorescent probe for homocysteine and its application in living cells. Dyes Pigm. 2017;140:212–221.
  • Jiang J-M, Yang P-A, Hsieh T-H, et al. Crystalline low-band gap polymers comprising thiophene and 2,1,3-benzooxadiazole units for bulk heterojunction solar cells. Macromolecules. 2011;44(23):9155–9163.
  • Zeng S, Yin L, Jiang X, et al. D–A–D low band gap molecule containing triphenylamine and benzoxadiazole/benzothiadiazole units: synthesis and photophysical properties. Dyes Pigm. 2012;95(2):229–235.
  • Liu Z, He J, Zhuang H, et al. Effect of single atom substitution in benzochalcogendiazole acceptors on the performance of ternary memory devices. J Mat Chem C. 2015;3(35):9145–9153.
  • Cristiano R, Vieira AA, Ely F, et al. Synthesis and characterization of luminescent hockey stick‐shaped liquid crystalline compounds. Liq Cryst. 2006;33(4):381–390.
  • Dierking I. The fluid smectic phases. textures of liquid crystals. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA; 2004. p. 91–122.
  • Yeap G-Y, Osman F, Imrie CT. Non-symmetric dimers: effects of varying the mesogenic linking unit and terminal substituent. Liq Cryst. 2015;42(4):543–554.
  • Chan T-N, Lu Z, Yam W-S, et al. Non-symmetric liquid crystal dimers containing an isoflavone moiety. Liq Cryst. 2012;39(3):393–402.
  • Fery-Forgues S, Lavabre D. Are fluorescence quantum yields so tricky to measure? A demonstration using familiar stationery products. J Chem Educ. 1999;76(9):1260.
  • Ghosh S, Das S, Kumar NR, et al. Effect of heteroatom (S/Se) juggling in donor-acceptor-donor (D-A-D) fused systems: synthesis and electrochemical polymerization. New J Chem. 2017;41(20):11568–11575.
  • Eccher J, Faria GC, Bock H, et al. Order induced charge carrier mobility enhancement in columnar liquid crystal diodes. ACS Appl Mater Inter. 2013;5(22):11935–11943.
  • Ghosh S, Kumar NR, Zade SS. Effects of chalcogen atom variation in chalcogenadiazole fused indolo[2,3-a]carbazoles. New J Chem. 2018;42(9):6889–6895.
  • Kawashima K, Osaka I, Takimiya K. Effect of chalcogen atom on the properties of naphthobischalcogenadiazole-based π-conjugated polymers. Chem Mater. 2015;27(19):6558–6570.

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