Investigation of the mesogenic behavior of alkoxy and fluorine tail terminated alkoxy nitrobiphenyls for chemoresponsive liquid crystals

References

• Gray GW. Synthetic chemistry related to liquid-crystals. Mol Cryst Liq. 1973;21(1–2):161–186.
   Web of Science ®Google Scholar
• Shah RR, Abbott NL. Principles for measurement of chemical exposure based on recognition-driven anchoring transitions in liquid crystals. Science. 2001;293(5533):1296–1299.
   PubMed Web of Science ®Google Scholar
• Nayani K, Rai P, Bao NQ, et al. Liquid crystals with interfacial ordering that enhances responsiveness to chemical targets. Adv Mater. 2018;30(27):7. DOI:10.1002/adma.201706707
   Web of Science ®Google Scholar
• Szilvási T, Bao N, Nayani K, et al. Redox‐triggered orientational responses of liquid crystals to chlorine gas. Angew Chem. 2018;130(31):9813–9817. DOI:10.1002/ange.201803194
   Google Scholar
• Gray GW, Harrison KJ, Nash JA. New family of nematic liquid-crystals for displays. Electron Lett. 1973;9(6):130–131.
   Web of Science ®Google Scholar
• Luo ZY, Peng FL, Chen HW, et al. Fast-response liquid crystals for high image quality wearable displays. Opt Mater Express. 2015;5(3):603–610. DOI:10.1364/OME.5.000603
   Web of Science ®Google Scholar
• Geelhaar T, Griesar K, Reckmann B. 125 years of liquid crystals—a scientific revolution in the home. Angew Chem Int Ed Engl. 2013;52(34):8798–8809.
   PubMed Web of Science ®Google Scholar
• Itahara T. Effect of the pentafluorophenyloxy group on liquid crystalline behaviour. Liq Cryst. 2005;32(1):115–118.
   Web of Science ®Google Scholar
• Wang KL, Szilvasi T, Gold J, et al. New room temperature nematogens by cyano tail termination of alkoxy and alkylcyanobiphenyls and their anchoring behavior on metal salt-decorated surface. Liq Cryst. 2020;47(4):540–556. DOI:10.1080/02678292.2019.1662116
   Web of Science ®Google Scholar
• Wang K, Jirka M, Rai P, et al. Synthesis and properties of hydroxy tail-terminated cyanobiphenyl liquid crystals. Liq Cryst. 2019;46(3):397–407. DOI:10.1080/02678292.2018.1502373
   Web of Science ®Google Scholar
• Wang K, Rai P, Fernando A, et al. Synthesis and properties of fluorine tail-terminated cyanobiphenyls and terphenyls for chemoresponsive liquid crystals. Liq Cryst. 2020;47(1):3–16. DOI:10.1080/02678292.2019.1616228
   Web of Science ®Google Scholar
• Wang KL, Rahman MS, Szilvasi T, et al. Influence of multifluorophenyloxy terminus on the mesomorphism of the alkoxy and alkyl cyanobiphenyl compounds in search of new ambient nematic liquid crystals and mixtures. Liq Cryst. 2021;48(5):672–688. DOI:10.1080/02678292.2020.1810792
   Web of Science ®Google Scholar
• Rupar I, Mulligan KM, Roberts JC, et al. Elucidating the smectic a-promoting effect of halogen end-groups in calamitic liquid crystals. J Mater Chem C. 2013;1(23):3729–3735. DOI:10.1039/c3tc30534a
   Web of Science ®Google Scholar
• Davis EJ, Mandle RJ, Russell BK, et al. Liquid-crystalline structure-property relationships in halogen-terminated derivatives of cyanobiphenyl. Liq Cryst. 2014;41(11):1635–1646. DOI:10.1080/02678292.2014.940505
   Web of Science ®Google Scholar
• Gibb CJ, Storey JMD, Imrie CT. A convenient one-pot synthesis, and characterisation of the ω-bromo-1-(4-cyanobiphenyl-4’-yl) alkanes (CBnBr). Liq Cryst. 2022;1–11. DOI:10.1080/02678292.2022.2084568
   Web of Science ®Google Scholar
• Kumar S, Pal SK. The first examples of terminally thiol-functionalized alkoxycyanobiphenyls. Liq Cryst. 2005;32(5):659–661.
   Web of Science ®Google Scholar
• Zhu SB, Jin CG, Li W, et al. The effect of intermolecular actions on the mesomorphic properties of alkenoxy biphenyl-based liquid crystals. J Mol Liq. 2019;296:8.
   Web of Science ®Google Scholar
• Mandle RJ, Cowling SJ, Sage I, et al. Relationship between molecular association and re-entrant phenomena in polar calamitic liquid crystals. J Phys Chem B. 2015;119(7):3273–3280. DOI:10.1021/jp512093j
   PubMed Web of Science ®Google Scholar
• Mandle RJ, Cowling SJ, Goodby JW. Evaluation of 4-alkoxy-4 ’-nitrobiphenyl liquid crystals for use in next generation scattering LCDs. RSC Adv. 2017;7(64):40480–40485.
   Web of Science ®Google Scholar
• Zugenmaier P, Kuczynski W. Comparison of the crystal and molecular structures of three similar 4-heptyl-biphenyl compounds: 4-heptyl-4′-cyanobiphenyl, 4-heptyl-3′-cyanobiphenyl, and 4-heptyl-4′-nitrobiphenyl. Mol Cryst Liq Cryst. 2006;457(1):93–103.
   Web of Science ®Google Scholar
• Yamada S, Rokusha Y, Kawano R, et al. Mesogenic gold complexes showing aggregation-induced enhancement of phosphorescence in both crystalline and liquid-crystalline phases. Faraday Discuss. 2017;196:269–283.
   PubMed Web of Science ®Google Scholar
• Jones B, Chapman F. 337. The nitration of esters of 4-hydroxydiphenyl. The preparation of 4-hydroxy-4′-and-2′-nitrodiphenyls. J Chem Soc. 1952;1829–1832. DOI:10.1039/JR9520001829
   Web of Science ®Google Scholar
• Ding R, He Y, Wang X, et al. Treatment of alcohols with tosyl chloride does not always lead to the formation of tosylates. Molecules. 2011;16(7):5665–5673. DOI:10.3390/molecules16075665
   PubMed Web of Science ®Google Scholar
• Kabalka GW, Varma M, Varma RS, et al. Tosylation of alcohols. J Org Chem. 1986;51(12):2386–2388. DOI:10.1021/jo00362a044
   Web of Science ®Google Scholar
• Frisch M, Trucks G, Schlegel HB, et al. Gaussian 09, revision d. 01, gaussian. Wallingford CT: Inc; 2009. p. 201.
   Google Scholar
• Perdew JP, Burke K, Ernzerhof M. Generalized gradient approximation made simple (vol 77, pg 3865, 1996). Phys Rev Lett. 1997;78(7):1396.
   Web of Science ®Google Scholar
• Grimme S, Antony J, Ehrlich S, et al. A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. J Chem Phys. 2010;132(15):19. DOI:10.1063/1.3382344
   Web of Science ®Google Scholar
• Marenich AV, Cramer CJ, Truhlar DG. Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. J Phys Chem B. 2009;113(18):6378–6396.
   PubMed Web of Science ®Google Scholar
• Weigend F, Ahlrichs R. Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: design and assessment of accuracy. Phys Chem Chem Phys. 2005;7(18):3297–3305.
   Google Scholar
• Zhao Y, Truhlar DG. The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four m06-class functionals and 12 other functionals. Theor Chem Acc. 2008;120(1–3):215–241.
   Web of Science ®Google Scholar
• Yu HZ, Szilvasi T, Rai P, et al. Computational chemistry-guided design of selective chemoresponsive liquid crystals using pyridine and pyrimidine functional groups. Adv Funct Mater. 2018;28(13):10. DOI:10.1002/adfm.201703581
   Web of Science ®Google Scholar
• Szilvasi T, Bao NQ, Yu HZ, et al. The role of anions in adsorbate-induced anchoring transitions of liquid crystals on surfaces with discrete cation binding sites. Soft Matter. 2018;14(5):797–805. DOI:10.1039/C7SM01981E
   PubMed Web of Science ®Google Scholar
• Collings PJ, and Hird M. Introduction to liquid crystals chemistry and physics. London: CRC Press; 2017.
   Google Scholar
• Roling LT, Scaranto J, Herron JA, et al. Towards first-principles molecular design of liquid crystal-based chemoresponsive systems. Nat Commun. 2016;7(1):7. DOI:10.1038/ncomms13338
   Web of Science ®Google Scholar
• Bao NQ, Gold JI, Szilvasi T, et al. Designing chemically selective liquid crystalline materials that respond to oxidizing gases. J Mater Chem C. 2021;9(20):6507–6517. DOI:10.1039/D1TC00544H
   PubMed Web of Science ®Google Scholar