Fluorescent liquid crystals with rod-shaped π-conjugated hydrocarbon core

References

• Goodby JW, Collings JP, Kato T, et al., editors. Handbook of Liquid Crystals. 2nd ed. Weinheim: Wiley-VCH; 2014.
   Google Scholar
• Wöhrle T, Wurzbach I, Kirres J, et al. Discotic liquid crystals. Chem Rev. 2016;116:1139–1241.
   PubMed Web of Science ®Google Scholar
• Laschat S, Baro A, Steinke N, et al. Discotic liquid crystals: from tailor-made synthesis to plastic electronics. Angew Chem Int Ed. 2007;46:4832–4887.
   PubMed Web of Science ®Google Scholar
• Yasuda T, Shimizu T, Lin F, et al. Electro-functional octupolar π-conjugated columnar liquid crystals. J Am Chem Soc. 2011;133:13437–13444.
   PubMed Web of Science ®Google Scholar
• Garcia-Frutos EM, Pandey UK, Termine R, et al. High charge mobility in discotic liquid-crystalline triindoles: just a core business? Angew Chem Int Ed. 2011;50:7399–7402.
   PubMed Web of Science ®Google Scholar
• An Z, Yu J, Domercq B, et al. Room-temperature discotic liquid-crystalline coronene diimides exhibiting high charge-carrier mobility in air. J Mater Chem. 2009;19:6688–6689.
   Web of Science ®Google Scholar
• Feng C, Ding Y-H, Han X-D, et al. Triphenylene 2,3-dicarboxylic imides as luminescent liquid crystals: mesomorphism, optical and electronic properties. Dyes Pigm. 2017;139:87–96.
   Web of Science ®Google Scholar
• Gupta RK, Pradhan B, Pathak SK, et al. Perylo[1,12-b,c,d]thiophene tetraesters: a new class of luminescent columnar liquid crystals. Langmuir. 2015;31:8092–8100.
   PubMed Web of Science ®Google Scholar
• De Halleux V, Calbert J-P, Brocorens P, et al. 1,3,6,8-Tetraphenylpyrene derivatives: towards fluorescent liquid crystalline columns? Adv Funct Mater. 2004;14:649 659.
   Web of Science ®Google Scholar
• Chen Z, Stepanenko V, Dehm V, et al. Photoluminescence and conductivity of self-assembled π–π stacks of perylene bisimide dyes. Chem Eur J. 2007;13:436–449.
   PubMed Web of Science ®Google Scholar
• Hayer A, de Halleux V, Köhler A, et al. Highly fluorescent crystalline and liquid crystalline columnar phases of pyrene-based structures. J Phys Chem B. 2006;110:7653–7659.
   PubMed Web of Science ®Google Scholar
• Hoeg BP, Gin DL. Polymerizable hexacatenar liquid crystals containing a luminescent oligo(p-phenylenevinylene) core. Liq Cryst. 2004;31:185–199.
   Web of Science ®Google Scholar
• Hsu H-F, Chien S-J, Chen -H-H, et al. Mesogenic and optical properties of α,α′-bis(4-alkoxyphenylethynyl)-oligothiophenes. Liq Cryst. 2005;32:683–689.
   Web of Science ®Google Scholar
• Puterová Z, Romiszewski J, Mieczkowski J, et al. Synthesis and study of newrod-like mesogens containing 2-aminothiophene unit. Tetrahedron. 2012;68:8172–8180.
   Web of Science ®Google Scholar
• Lai CK, Liu H-C, Cheng K-L, et al. Heterocyclic benzoxazole-based liquid crystals. Liq Cryst. 2005;32:85–94.
   Web of Science ®Google Scholar
• Kim S, Park SY. Synthesis and properties of highly fluorescent liquid crystals containing benzoxazole moiety. Mol Cryst Liq Cryst. 1999;337:405–408.
   Web of Science ®Google Scholar
• Xu Y, Chen X, Zhao F, et al. Synthesis and properties of substituted benzoxazole-terminated liquid crystals. Liq Cryst. 2013;40:197–215.
   Web of Science ®Google Scholar
• Buchs J, Gäbler M, Janietz D, et al. Coumarin-based emissive liquid crystals. Liq Cryst. 2014;41:1605–1618.
   Web of Science ®Google Scholar
• Han J, Wang F-L, Zhang F-Y, et al. Synthesis, mesomorphic behaviour and photo-luminescent property of new mesogens containing 1,3,4-oxadiazolefluorophore. Liq Cryst. 2010;37:1521–1527.
   Web of Science ®Google Scholar
• Sung -H-H, Lin H-C. Effect of polar substituents on the properties of 1,3,4-oxadiazole-based liquid crystalline materials containing asymmetric cores. Liq Cryst. 2004;31:831–840.
   Web of Science ®Google Scholar
• Han J, Wang X, Chang X-Y, et al. Fluorescent liquid crystalline compounds with 1,3,4-oxadiazole and benzo[b]thiophene units. Liq Cryst. 2012;39:669–674.
   Web of Science ®Google Scholar
• 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;39:1099–1111.
   Web of Science ®Google Scholar
• Vieira AA, Cristiano R, Bortoluzzi AJ, et al. Luminescent 2,1,3-benzothiadiazole-based liquid crystalline compounds. J Mol Struct. 2008;875:364–371.
   Web of Science ®Google Scholar
• Aguiar LO, Regis E, Tuzimoto P, et al. Investigation of thermal and luminescent properties in 4,7-diphenylethynyl-2,1,3-benzothiadiazole systems. Liq Cryst. 2018;45:49–58.
   Web of Science ®Google Scholar
• Martinez-Abadia M, Robles-Hernández B, Villacampa B, et al. Cyanostilbene bent-core molecules: a route to functional materials. J Mater Chem C. 2015;3:3038–3048.
   Web of Science ®Google Scholar
• Gao H, Cheng H, Liu Q, et al. Tolane-based bent bolaamphiphiles forming liquid crystalline hexagonal honeycombs with trigonal symmetry. New J Chem. 2015;39:2060–2066.
   Web of Science ®Google Scholar
• Yoon S-J, Kim JH, Kim KS, et al. Mesomorphic organization and thermochromic luminescence of dicyanodistyrylbenzene-based phasmidic molecular disks: uniaxially aligned hexagonal columnar liquid crystals at room temperature with enhanced fluorescence emission and semiconductivity. Adv Funct Mater. 2012;22:61–69.
   Web of Science ®Google Scholar
• Hoag BP, Gin DL. Fluorescent phasmidic liquid crystals. Adv Mater. 1998;10:1546–1551.
   Web of Science ®Google Scholar
• Sagara Y, Kato T. Stimuli-responsive luminescent liquid crystals: change of photoluminescent colors triggered by a shear-induced phase transition. Angew Chem Int Ed. 2008;47:5175–5178.
   PubMed Web of Science ®Google Scholar
• Pérez A, Serrano JL, Sierra T, et al. Control of self-assembly of a 3-hexen-1,5-diyne derivative: toward soft materials with an aggregation-induced enhancement in emission. J Am Chem Soc. 2011;133:8110–8113.
   PubMed Web of Science ®Google Scholar
• Lehmann M, Maier P, Grüne M, et al. Crowded star mesogens: guest-controlled stability of mesophases from unconventional liquid-crystal molecules. Chem Eur J. 2017;23:1060–1068.
   PubMed Web of Science ®Google Scholar
• Maier P, Grüne M, Lehmann M. A star-shaped oligo(phenylenevinylene) liquid crystal host with an anthracene guest – a double nanosegregating supermesogen. Chem Eur J. 2017;23:1018–1022.
   PubMed Web of Science ®Google Scholar
• Hennrich G, Ortiz PD, Cavero E, et al. Biphenyl-based disc- vs. rod-shaped phenylacetylenes: mesomorphism and electronic properties. Eur J Org Chem. 2008;27:4575–4579.
   Web of Science ®Google Scholar
• Lu H, Zhang S, Ding A, et al. A luminescent liquid crystal with multistimuli tunable emission colors based on different molecular packing structures. New J Chem. 2014;38:3429–3433.
   Web of Science ®Google Scholar
• Goel M, Jayakannan M. Supramolecular liquid crystalline π-conjugates: the role of aromatic π-stacking and van der waals forces on the molecular self-assembly of oligophenylene vinylenes. J Phys Chem B. 2010;114:12508–12519.
   PubMed Web of Science ®Google Scholar
• Sentman AC, Gin DL. Fluorescent trimeric liquid crystals: modular design of emissive mesogens. Adv Mater. 2001;13:1398–1401.
   Web of Science ®Google Scholar
• Bacher A, Bentley PG, Bradley DDC, et al. Synthesis and characterisation of a conjugated reactive mesogen. J Mater Chem. 1999;9:2985–2989.
   Web of Science ®Google Scholar
• Cheng Z, Zang Y, Li Y, et al. A chiral luminescent liquid crystal with a tolane unit. Liq Cryst. 2016;43:777–782.
   Web of Science ®Google Scholar
• Yamada S, Miyano K, Konno T, et al. Fluorine-containing bistolanes as light-emitting liquid crystalline molecules. Org Biomol Chem. 2017;15:5949–5958.
   PubMed Web of Science ®Google Scholar
• Wu ST, Finkenzeller U, Reiffenrath V. Physical properties of diphenyldiacetylenic liquid crystals. J Appl Phys. 1989;65:4372–4376.
   Web of Science ®Google Scholar
• Peng Z, Wang Q, Liu Y, et al. Electrooptical properties of new type fluorinated phenyl-tolane isothiocyanate liquid crystal compounds. Liq Cryst. 2016;43:276–284.
   Web of Science ®Google Scholar
• Herman J, Dziaduszek J, Dabrowski R, et al. Novel high birefringent isothiocyanates based on quaterphenyl and phenylethynyltolane molecular cores. Liq Cryst. 2013;40:1174–1182.
   Web of Science ®Google Scholar
• Heck RF, Nolley JP. Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides. J Org Chem. 1972;37:2320–2322.
   Web of Science ®Google Scholar
• Sonogashira K. Development of Pd–Cu catalyzed cross-coupling of terminal acetylenes with sp2-carbon halides. J Organomet Met. 2002;653:46–49.
   Web of Science ®Google Scholar
• Chinchilla R, Nájera C. The Sonogashira reaction: a booming methodology in synthetic organic chemistry. Chem Rev. 2007;107:874–922.
   PubMed Web of Science ®Google Scholar
• Song X, Li J, Zhang S. Preparation and liquid crystalline properties of a new type of hydrogen-bonded liquid crystals containing an aryl-acetylene moiety. Liq Cryst. 2003;30:1123–1128.
   Web of Science ®Google Scholar
• Janietz D, Praefcke K, Singer D. New disc-shaped mesogens based on pentakis(phenylethynyl)benzene derivatives. Liq Cryst. 1993;13:247–253.
   Web of Science ®Google Scholar
• Weissflog W. Vol. 2B, Chapter XI. Laterally substituted and swallow-tailed liqud crystals. In: Demus D, Goodby J, Gray GW, et al., editors. Handbook of Liquid Crystals. Weinheim, Chichester, Brisbane, Singapore, Toronto: Wiley-VCH; 1998. p. 835–863.
   Google Scholar
• Andersch J, Tschierske C, Diele S, et al. Synthesis and liquid-crystalline properties of novel laterally connected twins: the influence of the connecting topology and the length of the rigid core. J Mater Chem. 1996;6:1297–1307.
   Web of Science ®Google Scholar
• Janietz D, Kohlmeier A. Nanoscale segregation, molecular recognition and fluorophobic effect – from molecular design towards complex mesophase morphologies. Liq Cryst. 2009;36:685–703.
   Web of Science ®Google Scholar
• Tschierske C. Micro-segregation, molecular shape and molecular topology – partners for the design of liquid crystalline materials with complex mesophase morphologies. J Mater Chem. 2001;11:2647–2671.
   Web of Science ®Google Scholar
• Hird M. Fluorinated liquid crystals – properties and applications. Chem Soc Rev. 2007;36:2070–2095.
   PubMed Web of Science ®Google Scholar
• Tschierske C. Fluorinated liquid crystals: design of soft nanostructures and increased complexity of self-assembly by perfluorinated segments. Top Curr Chem. 2012;318:1–108.
   PubMed Web of Science ®Google Scholar
• Marty’nski T, Mykowska E, Baumann D. Spectral properties of fluorescent dyes in nematic liquid crystals. J Mol Struct. 1994;325:161–167.
   Web of Science ®Google Scholar
• Iwanaga H, Naito K, Effenberger F. Oligothiophene dyes for guest-host liquid crystal displays. Liq Cryst. 2000;27:115–123.
   Web of Science ®Google Scholar
• Zhang X, Yamaguchi R, Moriyama K, et al. Highly dichroic benzo-2,1,3-thiadiazole dyes containing five linearly π-conjugated aromatic residues, with fluorescent emission ranging from green to red, in a liquid crystal guest–host system. J Mater Chem. 2006;16:736–740.
   Web of Science ®Google Scholar
• Coles HJ, Lester GA, Owen H. Fluorescent dye guest-host effects in advanced ferroelectric liquid crystals. Liq Cryst. 1993;14:1039–1045.
   Web of Science ®Google Scholar
• Beer A, Scherowsky G, Owen H, et al. Fluorescent ferroelectric liquid crystalline copolyacrylates. Liq Cryst. 1995;19:565–572.
   Web of Science ®Google Scholar
• Hikmet RAM, Lub J. Anisotropic networks and gels obtained by photopolymerisation in the liquid crystalline state: synthesis and applications. Prog Polym Sci. 1996;21:1165–1209.
   Web of Science ®Google Scholar
• Contoret AEA, Farrar SR, Jackson PO, et al. Polarized electroluminescence from an anisotropic nematic network on a non-contact photoalignment layer. Adv Mater. 2000;12:971–974.
   Web of Science ®Google Scholar
• Yao Y-H, Kung L-R, Chang S-W, et al. Synthesis of UV-curable liquid crystalline diacrylates for the application of polarized electroluminescence. Liq Cryst. 2006;33:33–39.
   Web of Science ®Google Scholar
• Thiem H, Jandke M, Hanft D, et al. Synthesis and orientation of fluorene containing reactive mesogens. Macromol Chem Phys. 2006;207:370–381.
   Web of Science ®Google Scholar
• Millaruelo M, Oriol L, Serrano JL, et al. Emissive anisotropic polymeric materials derived from liquid crystalline fluorenes. Mol Cryst Liq Cryst. 2004;411:451–466.
   Web of Science ®Google Scholar
• Sánchez C, Villacampa B, Cases R, et al. Polarized photoluminescence and order parameters of “in situ” photopolymerized liquid crystal films. J Appl Phys. 2000;87:274–279.
   Web of Science ®Google Scholar
• Sánchez C, Alcalá R, Cases R, et al. Photoluminescence stability of a cyanoterphenyl chromophore in liquid crystalline polymeric systems. J Appl Phys. 2000;88:7124–7128.
   Web of Science ®Google Scholar
• van der Zande BMI, Steenbakkers J, Lub J. Mass transport phenomena during lithographic polymerization of nematic monomers monitored with interferometry. J Appl Phys. 2005;97:123519-1–123519-8.
   Web of Science ®Google Scholar
• Aguilera C, Sáez P, Morel M, et al. Bireactive calamitic liquid crystals derived from fluorene ester linkage. Liq Cryst. 2007;34:1233–1242.
   Web of Science ®Google Scholar