Theoretical, experimental and optical study of new thiophene-based liquid crystals and their positional isomers

References

• O’Neill M, Kelly SM. Liquid crystals for charge transport, luminescence, and photonics. Adv Mater. 2003;15:1135–1146.
   Web of Science ®Google Scholar
• Kumar S. Liquid crystals: experimental study of physical properties and phase transitions. Cambridge: Cambridge University Press; 2001.
   Google Scholar
• Wu L-H, Wang Y-C, Hsu C-S. Synthesis and characterization of thiophene-containing liquid crystals. Liq Cryst. 2000;27:1503–1513.
   Web of Science ®Google Scholar
• Dos Santos DR, Silva de Oliveira AG, Coelho RL, et al. Synthesis of liquid crystals materials derived from oxadiazole, isoxazole and tetrazole heterocycles. Arkivoc. 2008;2008:157–166.
   Google Scholar
• Srividhya D, Manjunathan S, Thirumaran S. Synthesis and characterization of new heterocyclic liquid crystals. J Chem. 2009;6:928–937.
   Web of Science ®Google Scholar
• Thaker B, Patel B, Dhimmar Y, et al. Synthesis, characterization and mesomorphic properties of new rod-like thiophene based liquid crystals. Mol Cryst Liq Cryst. 2012;562:98–113.
   Web of Science ®Google Scholar
• Park YS, Kim D, Lee H, et al. Donor− acceptor− donor-type liquid crystal with a pyridazine core. Org Lett. 2006;8:4699–4702.
   PubMed Web of Science ®Google Scholar
• Geelhaar T. Ferroelectric mixtures and their physico-chemical properties. Ferroelectrics. 1988;85:329–349.
   Web of Science ®Google Scholar
• 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;12:1336–1339.
   Web of Science ®Google Scholar
• Barbarella G, Zambianchi M, Pudova O, et al. Oligothiophene isothiocyanates as a new class of fluorescent markers for biopolymers. J Am Chem Soc. 2001;123:11600–11607.
   PubMed Web of Science ®Google Scholar
• Goodby JW, Mandle RJ, Davis EJ, et al. What makes a liquid crystal? The effect of free volume on soft matter. Liq Cryst. 2015;42:593–622.
   Web of Science ®Google Scholar
• Goodby JW. Free volume, molecular grains, self-organisation, and anisotropic entropy: machining materials. Liq Cryst. 2017;44:1755–1763.
   Web of Science ®Google Scholar
• Imrie CT, Henderson PA, Yeap G-Y. Liquid crystal oligomers: going beyond dimers. Liq Cryst. 2009;36:755–777.
   Web of Science ®Google Scholar
• Ahmed H, Hagar M, Saad G. Impact of the proportionation of dialkoxy chain length on the mesophase behaviour of Schiff base/ester liquid crystals; experimental and theoretical study. Liq Cryst. 2019;46:1611–1620.
   Web of Science ®Google Scholar
• Nesrullajev A, Bilgin-Eran B. Mesomorphic, morphologic and thermotropic properties of 4-hexyl-N-(4-hexadecyloxysalicylidene) aniline. Mater Chem Phys. 2005;93:21–25.
   Web of Science ®Google Scholar
• Yasa-Sahin O, Yazici O, Karaagac B, et al. A new liquid crystal of considerable value for the separation of closely related solvents by gas chromatography. Liq Cryst. 2010;37:1111–1118.
   Web of Science ®Google Scholar
• Canli NY, Günes S, Pivrikas A, et al. (S)-5-octyloxy-2-[{4-(2-methylbuthoxy)-phenylimino}-methyl]-phenol liquid crystalline compound as additive into polymer solar cells. Sol Energy Mater Sol Cells. 2010;94:1089–1099.
   Web of Science ®Google Scholar
• Hagar M, Ahmed H, Saad G. Synthesis and mesophase behaviour of Schiff base/ester 4-(arylideneamino) phenyl-4 ″-alkoxy benzoates and their binary mixtures. J Mol Liq. 2019;273:266–273.
   Web of Science ®Google Scholar
• Ahmed H, Hagar M, El-Sayed TB, et al. Schiff base/ester liquid crystals with different lateral substituents: mesophase behaviour and DFT calculations. Liq Cryst. 2019;46:1156–1166.
   Web of Science ®Google Scholar
• Hagar M, Ahmed H, Saad G. Mesophase stability of new Schiff base ester liquid crystals with different polar substituents. Liq Cryst. 2018;45:1324–1332.
   Web of Science ®Google Scholar
• Salamończyk M, Vaupotič N, Pociecha D, et al. Multi-level chirality in liquid crystals formed by achiral molecules. Nat Commun. 2019;10:1922.
   PubMed Web of Science ®Google Scholar
• Abberley JP, Killah R, Walker R, et al. Heliconical smectic phases formed by achiral molecules. Nat Commun. 2018;9:228.
   PubMed Web of Science ®Google Scholar
• Paterson DA, Crawford CA, Pociecha D, et al. The role of a terminal chain in promoting the twist-bend nematic phase: the synthesis and characterisation of the 1-(4-cyanobiphenyl-4′-yl)-6-(4-alkyloxyanilinebenzylidene-4′-oxy) hexanes. Liq Cryst. 2018;45:2341–2351.
   Web of Science ®Google Scholar
• Yang X, Mo L, Hu M, et al. New isothiocyanato liquid crystals containing thieno [3, 2-b] thiophene central core. Liq Cryst. 2018;45:1294–1302.
   Web of Science ®Google Scholar
• Pratap G, Malkar D, Varathan E, et al. 3-Cyano thiophene-based π-conjugated mesogens: XRD and 13C NMR investigations. Liq Cryst. 2019;46:680–693.
   Web of Science ®Google Scholar
• Campbell NL, Duffy WL, Thomas GI, et al. Nematic 2, 5-disubstituted thiophenes. J Mater Chem. 2002;12:2706–2721.
   Web of Science ®Google Scholar
• Sharma S, Lacey D, Wilson P. Synthesis and characterization of a range of heterocyclic liquid crystalline materials incorporating the novel thiophene-pyrimidine moiety. Liq Cryst. 2003;30:451–461.
   Web of Science ®Google Scholar
• Nishiyama I, Goodby JW. A non-chiral swallow-tailed liquid crystal exhibiting a smectic C phase that has an antiferroelectric structure. J Mater Chem. 1992;2:1015–1023.
   Web of Science ®Google Scholar
• Byron DJ, Komitov L, Matharu AS, et al. The synthesis and characterisation of a novel thiophene-based liquid crystal exhibiting ferro-, ferri- and antiferro-electric phase types. J Mater Chem. 1996;6:1871–1878.
   Web of Science ®Google Scholar
• Seed A, Hird M, Styring P, et al. Heterocyclic esters exhibiting frustrated liquid crystal phases. Mol Cryst Liq Cryst Sci Technol Sect A Mol Cryst Liq Cryst. 1997;299:19–25.
   Web of Science ®Google Scholar
• Matharu A, Wilson R, Grover C. Novel bi-and ter-thiophenes exhibiting ferri-and antiferro-electric behaviour. Mol Cryst Liq Cryst Sci Technol Sect A Mol Cryst Liq Cryst. 1999;332:303–311.
   Web of Science ®Google Scholar
• Kiryanov AA, Seed AJ, Sampson P. Ring fluorinated thiophenes: applications to liquid crystal synthesis. Tetrahedron Lett. 2001;42:8797–8800.
   Web of Science ®Google Scholar
• Kiryanov AA, Sampson P, Seed AJ. Synthesis and mesomorphic properties of 1, 1-difluoroalkyl-substituted biphenylthienyl and terphenyl liquid crystals. A comparative study of mesomorphic behavior relative to alkyl, alkoxy and alkanoyl analogs. J Mater Chem. 2001;11:3068–3077.
   Web of Science ®Google Scholar
• Seed A. Synthesis of self-organizing mesogenic materials containing a sulfur-based five-membered heterocyclic core. Chem Soc Rev. 2007;36:2046–2069.
   PubMed Web of Science ®Google Scholar
• Huang Y, Luo Z, Cheng X, et al. Synthesis and mesomorphic behaviour of new 5‐substituted 4‐(thien‐2‐yl) phenyl benzoates. Liq Cryst. 2009;36:61–66.
   Web of Science ®Google Scholar
• Bartle K, Campbell N, Duffy WL, et al. Nematic thiophenes for STN-LCDS and flexoelectric LCDS. Mol Cryst Liq Cryst Sci Technol Sect A Mol Cryst Liq Cryst. 2001;364:881–888.
   Web of Science ®Google Scholar
• Kossmehl G, Hoppe F. Liquid crystalline compounds in the thiophene series, Part 9: synthesis and characterization of liquid crystalline vinylenes with two mesogenic groups containing exclusively thiophene system. Mol Cryst Liq Cryst Sci Technol Sect A Mol Cryst Liq Cryst. 1994;257:169–179.
   Web of Science ®Google Scholar
• KOssMEHL G, Hoppe FD. Liquid crystalline compounds in the thiophene series XIII. Synthesis and characterization of ‘oligomeric’liquid crystalline model compounds with vinylene units, thiophene ring systems and hexamethylene chains. Liq Cryst. 1997;22:137–144.
   Web of Science ®Google Scholar
• Gray G, Hird M, Lacey D, et al. The synthesis and transition temperatures of some fluoro-substituted 4-Cyanophenyl and 4-Cyanobiphenyl-4′-yl 4-Pentyl-and 4-Butoxy-Benzoates. Mol Cryst Liq Cryst. 1989;172:165–189.
   Web of Science ®Google Scholar
• Lobo NP, Das BB, Narasimhaswamy T, et al. Molecular topology of three ring nematogens from 13 C–1 H dipolar couplings. RSC Adv. 2014;4:33383–33390.
   Web of Science ®Google Scholar
• Narasimhaswamy T, Somanathan N, Lee D, et al. Synthesis and 13C CPMAS NMR characterization of novel thiophene-based nematogens. Chem Mater. 2005;17:2013–2018.
   Web of Science ®Google Scholar
• Ahmed H, Hagar M, Alhaddad O. New chair shaped supramolecular complexes-based aryl nicotinate derivative; mesomorphic properties and DFT molecular geometry. RSC Adv. 2019;9:16366–16374.
   PubMed Web of Science ®Google Scholar
• Hagar M, Ahmed H, Alhaddad O. Experimental and theoretical approaches of molecular geometry and mesophase behaviour relationship of laterally substituted azopyridines. Liq Cryst. 2019;46:1440–1451.
   Web of Science ®Google Scholar
• Hagar M, Ahmed H, Alhaddad O. New azobenzene-based natural fatty acid liquid crystals with low melting point: synthesis, DFT calculations and binary mixtures. Liq Cryst. 2019;46:2223–2234.
   Web of Science ®Google Scholar
• Hagar M, Ahmed H, El-Sayed T, et al. Mesophase behavior and DFT conformational analysis of new symmetrical diester chalcone liquid crystals. J Mol Liq. 2019;285:96–105.
   Web of Science ®Google Scholar
• Ahmed HA, Hagar M, Alhaddad OA. Phase behavior and DFT calculations of laterally methyl supramolecular hydrogen-bonding complexes. Crystals. 2019;9:133.
   Web of Science ®Google Scholar
• Alnoman RB, Parveen S, Hagar M, et al. A new chiral Boron–dipyrromethene (BODIPY)–based fluorescent probe: molecular docking, DFT, antibacterial and antioxidant approaches. J Biomol Struct Dyn. 2019;1–19. DOI:10.1080/07391102.2019.1701555
   PubMed Web of Science ®Google Scholar
• Nafee SS, Hagar M, Ahmed HA, et al. The synthesis of new thermal stable Schiff base/ester liquid crystals: a computational, mesomorphic, and optical study. Molecules. 2019;24:3032.
   PubMed Web of Science ®Google Scholar
• Nafee SS, Hagar M, Ahmed HA, et al. New two rings Schiff base liquid crystals; ball mill synthesis, mesomorphic, Hammett and DFT studies. J Mol Liq. 2019;112161. DOI:10.1016/j.molliq.2019.112161
   Web of Science ®Google Scholar
• Alnoman R, Ahmed HA, Hagar M. Synthesis, optical, and geometrical approaches of new natural fatty acids’ esters/Schiff base liquid crystals. Molecules. 2019;24:4293.
   PubMed Web of Science ®Google Scholar
• Nugent S, Wang Q, Bruce D. The synthesis and characterization of nematic, heterocyclic imino‐esters. ChemInform. 1996;20(6):669–675.
   Google Scholar
• Frisch M, Trucks G, Schlegel HB, et al. Gaussian 09, revision a. 02. Wallingford, CT: Gaussian. Inc; 2009. p. 200.
   Google Scholar
• Dennington R, Keith T, Millam J. GaussView, version 5. Shawnee Mission, KS: Semichem Inc; 2009.
   Google Scholar
• Naoum MM, Metwally NH, Abd Eltawab MM, et al. Polarity and steric effect of the lateral substituent on the mesophase behaviour of some newly prepared liquid crystals. Liq Cryst. 2015;42:1351–1369.
   Web of Science ®Google Scholar
• Gray GW. The chemistry of liquid crystals. Philos Trans R Soc London Ser A. 1983;309:77–92.
   Web of Science ®Google Scholar
• Luckhurst G, Gray GW. The molecular physics of liquid crystals. London, UK: Academic press; 1979.
   Google Scholar
• Gray GW. Molecular structure and the properties of liquid crystals. London, UK: Academic press, Inc; 1962.
   Google Scholar
• Lizu M, Lutfor M, Surugau N, et al. Synthesis and characterization of ethyl cellulose–based liquid crystals containing azobenzene chromophores. Mol Cryst Liq Cryst. 2010;528:64–73.
   Web of Science ®Google Scholar
• Abberley JP, Jansze SM, Walker R, et al. Structure–property relationships in twist-bend nematogens: the influence of terminal groups. Liq Cryst. 2017;44:68–83.
   Web of Science ®Google Scholar
• Paterson DA, Gao M, Kim Y-K, et al. Understanding the twist-bend nematic phase: the characterisation of 1-(4-cyanobiphenyl-4′-yloxy)-6-(4-cyanobiphenyl-4′-yl) hexane (CB6OCB) and comparison with CB7CB. Soft Matter. 2016;12:6827–6840.
   PubMed Web of Science ®Google Scholar
• Hagar M, Ahmed HA, Saad GR. New calamitic thermotropic liquid crystals of 2-hydroxypyridine ester mesogenic core: mesophase behaviour and DFT calculations. Liq Cryst. 2019;1–11. DOI:10.1080/02678292.2019.1631967
   PubMed Web of Science ®Google Scholar