Biphenyls embedded Schiff base-bis esters: self-assembling behaviour, impact of additional aromatic ring and ester linkage and their DFT investigations

References

• Lowe AM, Abbott NL. Liquid crystalline materials for biological applications. Chem Mater [Internet]. 2012;24(5):746–758. doi: 10.1021/cm202632m
   PubMed Web of Science ®Google Scholar
• Kasch N. Liquid crystals: applications and industry. Liq Cryst Today [Internet]. 2013;22:70–71. doi: 10.1080/1358314X.2013.854953
   Google Scholar
• Gottarelli G, Samorí B. Some applications of liquid crystals in organic chemistry. Inorganica Chim Acta [Internet]. 1980;40:X10–X11. Available from: https://www.sciencedirect.com/science/article/pii/S0020169300920413
   Web of Science ®Google Scholar
• Brown GH. Properties and applications of liquid crystals. J Electron Mater [Internet]. 1973;2:403–430. doi: 10.1007/BF02660146
   Google Scholar
• Lagerwall JPF, Scalia G. A new era for liquid crystal research: applications of liquid crystals in soft matter nano-, bio- and microtechnology. Curr Appl Phys. [Internet]. 2012;12(6):1387–1412. doi: 10.1016/j.cap.2012.03.019
   Web of Science ®Google Scholar
• 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. [Internet]. 2013;52(34):8880–8896. doi: 10.1002/anie.201300903
   PubMed Web of Science ®Google Scholar
• Sultan AA, Fahmi AA, Saad GR, et al. Effect of orientation of lateral fluorine atom on the mesophase behaviour of azo/ester molecules with terminal naphthyl group. Liq Cryst [Internet]. 2019;46:2322–2333. doi: 10.1080/02678292.2019.1663283
   Web of Science ®Google Scholar
• Mandle RJ, Goodby JW. Designing principles and synthesis of materials for nematic liquid crystals. Handb Liq Cryst [Internet]. 2014;1–39. Available from: https://onlinelibrary.wiley.com/doi/abs/10.1002/9783527671403.hlc039
   Google Scholar
• Ahmed NHS, Saad GR, Ahmed HA, et al. New wide-stability four-ring azo/ester/Schiff base liquid crystals: synthesis, mesomorphic, photophysical, and DFT approaches. RSC Adv [Internet]. 2020;10(16):9643–9656. doi: 10.1039/C9RA10499B
   PubMed Web of Science ®Google Scholar
• Hagar M, Ahmed HA, Nafee SS, et al. The synthesis of new thermal stable schiff Base/Ester liquid crystals: a computational, mesomorphic, and optical study. Molecules [Internet]. 2019;24(17):3032. Available from: https://pubmed.ncbi.nlm.nih.gov/31438540
   PubMed Web of Science ®Google Scholar
• Selvarasu C, Kannan P. Effect of azo and ester linkages on rod shaped Schiff base liquid crystals and their photophysical investigations. J Mol Struct [Internet]. 2016;1125:234–240. doi: 10.1016/j.molstruc.2016.06.081
   Web of Science ®Google Scholar
• Wang X, Li Z, Zhao H, et al. New azobenzene liquid crystal with dihydropyrazole heterocycle and photoisomerization studies. R Soc Open Sci [Internet]. 2021;7(7):200474. doi: 10.1098/rsos.200474
   Web of Science ®Google Scholar
• Ahmed HA, Hagar M, El-Sayed TH, et al. Schiff base/ester liquid crystals with different lateral substituents: mesophase behaviour and DFT calculations. Liq Cryst [Internet]. 2019;46:1–11. doi: 10.1080/02678292.2019.1566581
   Web of Science ®Google Scholar
• Gibb CJ, Majewska M, Pociecha D, et al. Liquid crystal dimers and the twist-bend phases: non-symmetric dimers consisting of mesogenic units of differing lengths. Chemphyschem [Internet]. 2024;e202300848. Available from: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/cphc.202300848
   PubMedGoogle Scholar
• Abberley JP, Killah R, Walker R, et al. Heliconical smectic phases formed by achiral molecules. Nat Commun [Internet]. 2018;9(1):228. doi: 10.1038/s41467-017-02626-6
   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 [Internet]. 2020;299:112161. Available from: https://www.sciencedirect.com/science/article/pii/S0167732219333033
   Web of Science ®Google Scholar
• Hagar M, Ahmed HA, Saad GR. Synthesis and mesophase behaviour of schiff base/ester 4-(arylideneamino)phenyl-4″-alkoxy benzoates and their binary mixtures. J Mol Liq [Internet]. 2019;273:266–273. doi: 10.1016/j.molliq.2018.10.035
   Web of Science ®Google Scholar
• Ahmed HA, Hagar M, Alhaddad OA. New chair shaped supramolecular complexes-based aryl nicotinate derivative; mesomorphic properties and DFT molecular geometry. RSC Adv [Internet]. 2019;9(29):16366–16374. doi: 10.1039/C9RA02558H
   PubMed Web of Science ®Google Scholar
• Imrie CT, Henderson PA. Liquid crystal dimers and higher oligomers: between monomers and polymers. Chem Soc Rev [Internet]. 2007;36(12):2096–2124. doi: 10.1039/B714102E
   PubMed Web of Science ®Google Scholar
• Ahmed HA, Hagar M, Alhaddad OA. Phase behavior and DFT calculations of laterally methyl supramolecular hydrogen-bonding complexes. Crystals [Internet]. 2019;9(3):133. doi: 10.3390/cryst9030133
   Web of Science ®Google Scholar
• Imrie CT, Henderson PA, Yeap G-Y. Liquid crystal oligomers: going beyond dimers. Liq Cryst [Internet]. 2009;36:755–777. doi: 10.1080/02678290903157455
   Web of Science ®Google Scholar
• Tufaha N, Cruickshank E, Pociecha D, et al. Molecular shape, electronic factors, and the Ferroelectric Nematic Phase: investigating the impact of structural modifications. Chem A Eur J [Internet]. 2023;29(28):e202300073. Available from: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.202300073
   PubMed Web of Science ®Google Scholar
• Brown S, Cruickshank E, Storey JMD, et al. Multiple polar and non-polar nematic phases. Chemphyschem [Internet] 2021;22(24):2506–2510. doi: 10.1002/cphc.202100644
   PubMed Web of Science ®Google Scholar
• Mandle RJ, Cowling SJ, Goodby JW. A nematic to nematic transformation exhibited by a rod-like liquid crystal. Phys Chem Chem Phys [Internet]. 2017;19:11429–11435. doi: 10.1039/C7CP00456G
   PubMed Web of Science ®Google Scholar
• Nishikawa H, Shiroshita K, Higuchi H, et al. A fluid liquid-crystal material with highly polar order. Adv Mater [Internet]. 2017;29:1702354. doi: 10.1002/adma.201702354
   Web of Science ®Google Scholar
• Wan D, Yang X, Li J, et al. Synthesis and properties of 5,6-dihydro-4H-cyclopenta[b]thiophene-based nematic liquid crystals: a new access to mesogens with high birefringence and large dielectric anisotropy. J Mol Liq [Internet]. 2021;327:114827. Available from: https://www.sciencedirect.com/science/article/pii/S0167732220370690
   Web of Science ®Google Scholar
• Cigl M, Hampl F, Svoboda J, et al. Laterally substituted biphenyl benzoates ‒ synthesis and mesomorphic properties. Liq Cryst [Internet]. 2021;48:526–536. doi: 10.1080/02678292.2020.1794069
   Web of Science ®Google Scholar
• Al-Karawi AJM, OmarAli A-A, Awad AA, et al. Liquid crystal and photoluminescent properties of a series of symmetrical 1,2-bis(4-alkoxybenzylidene)hydrazines bearing long-tails of hydrocarbon chain. Liq Cryst [Internet]. 2021;48(3):412–422. doi: 10.1080/02678292.2020.1786175
   Web of Science ®Google Scholar
• Khan BC, Mukherjee PK. Isotropic to smectic-A phase transition in taper-shaped liquid crystal. J Mol Liq [Internet]. 2021;329:115539. Available from: https://www.sciencedirect.com/science/article/pii/S0167732221002658
   Web of Science ®Google Scholar
• Goodby JW. Free volume, molecular grains, self-organisation, and anisotropic entropy: machining materials. Liq Cryst [Internet]. 2017;44:1755–1763. doi: 10.1080/02678292.2017.1347293
   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 [Internet]. 2015;42(5):593–622. Available from: https://www.tandfonline.com/doi/abs/10.1080/02678292.2015.1030348
   Web of Science ®Google Scholar
• Karim MR, Sheikh MRK, Yahya R, et al. The effect of terminal substituents on crystal structure, mesophase behaviour and optical property of azo-ester linked materials. Liq Cryst [Internet]. 2016;43:1862–1874. doi: 10.1080/02678292.2016.1216620
   Web of Science ®Google Scholar
• Sardon SNF, Rahman NMMA, Karim MR, et al. Effects of lateral methyl and terminal substituents on thermal, mesomorphic and optical properties of azo-ester mesogens. J Mol Struct [Internet]. 2021;1225:129112. doi: 10.1016/j.molstruc.2020.129112
   Web of Science ®Google Scholar
• Jamain Z, Omar NF, Khairuddean M. Synthesis and determination of thermotropic liquid crystalline behavior of cinnamaldehyde-based molecules with two schiff base linking units. Molecules [Internet]. 2020;25(17):3780. doi: 10.3390/molecules25173780
   PubMed Web of Science ®Google Scholar
• Yeap G-Y, Osman F, Imrie CT. Non-symmetric dimers: effects of varying the mesogenic linking unit and terminal substituent. Liq Cryst [Internet]. 2015;42:543–554. doi: 10.1080/02678292.2015.1004843
   Web of Science ®Google Scholar
• Schroeder JP, Bristol DW. Liquid crystals. IV. Effects of terminal substituents on the nematic mesomorphism of p-phenylene dibenzoates. J Org Chem [Internet]. 1973;38:3160–3164. doi: 10.1021/jo00958a018
   Web of Science ®Google Scholar
• Dewar MJS, Goldberg RS. Effects of central and terminal groups on nematic mesophase stability. J Org Chem [Internet]. 1970;35:2711–2715. doi: 10.1021/jo00833a051
   Web of Science ®Google Scholar
• Horčic M, Svoboda J, Novotná V, et al. Bent-core dimers with top-to-bottom linkage between central units. RSC Adv [Internet]. 2018;8(41):22974–22985. doi: 10.1039/C8RA04108C
   PubMed Web of Science ®Google Scholar
• Pfletscher M, Mezger M, Giese M. On the impact of linking groups in hydrogen-bonded liquid crystals – a case study. Soft Matter. [Internet]. 2018;14(30):6214–6221. doi: 10.1039/C8SM00802G
   PubMed Web of Science ®Google Scholar
• He W-L, Gu H, Zhao P, et al. Synthesis and mesophase behaviour of branched azobenzene-based supramolecular hydrogen-bonded liquid crystals. Liq Cryst [Internet]. 2017;44(3):593–602. doi: 10.1080/02678292.2017.1306635
   Web of Science ®Google Scholar
• Ocak H, Ahlatcıoğlu Özerol E, Çelikel FÇ, et al. The synthesis, mesomorphic and dielectric investigation of new unsymmetrical bent-core mesogens derived from 3-hydroxybenzoic acid. Chem Pap [Internet]. 2020;74(11):3899–3911. doi: 10.1007/s11696-020-01203-4
   Web of Science ®Google Scholar
• Kelker H, Scheurle B. A liquid-crystalline (nematic) phase with a particularly low solidification point. Angew Chemie Int. Ed English [Internet]. 1969;8(11):884–885. Available from: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.196908841
   Google Scholar
• Hagar M, Ahmed HA, Saad GR. Mesophase stability of new Schiff base ester liquid crystals with different polar substituents. Liq Cryst [Internet]. 2018;45(9):1324–1332. doi: 10.1080/02678292.2018.1435831
   Web of Science ®Google Scholar
• Elgueta EY, Parra ML, Barberá J, et al. New polycatenar Schiff bases derived from 1,3,4-thiadiazole: synthesis, mesomorphism and luminescence behaviour. Liq Cryst [Internet]. 2016;43(11):1649–1658. doi: 10.1080/02678292.2016.1193907
   Web of Science ®Google Scholar
• Sastry PS, Pardhasaradhi P, Srinivasu C, et al. Synthesis, characterisation and phase transition studies in N-(-4-ethyloxybenzylydene)-4’-alkoxyanilines. Liq Cryst [Internet]. 2016;43(5):632–638. doi: 10.1080/02678292.2015.1131342
   Web of Science ®Google Scholar
• Henderson PA, Imrie CT. Methylene-linked liquid crystal dimers and the twist-bend nematic phase. Liq Cryst [Internet]. 2011;38(11–12):1407–1414. doi: 10.1080/02678292.2011.624368
   Web of Science ®Google Scholar
• Shubashree S, Sadashiva BK, Dhara S. Banana-shaped mesogens: effect of 2-methylresorcinol as the central unit on the mesomorphic properties of five-ring esters. Liq Cryst [Internet]. 2002;29(6):789–797. doi: 10.1080/02678290210138830
   Web of Science ®Google Scholar
• Kohout M, Svoboda J, Novotná V, et al. Non-symmetrical bent-shaped liquid crystals based on a laterally substituted naphthalene central core with four ester groups. Liq Cryst [Internet]. 2011;38(9):1099–1110. doi: 10.1080/02678292.2011.596949
   Web of Science ®Google Scholar
• Tasaka T, Okamoto H, Petrov VF, et al. Liquid crystalline properties of dissymmetric molecules VI. The effect of alkyl chain length on molecular arrangement in the smectic a phase in three-aromatic-ring systems with two ester groups. Liq Cryst [Internet]. 2001;28(7):1025–1034. doi: 10.1080/02678290110045906
   Web of Science ®Google Scholar
• Duan M, Tasaka T, Okamoto H, et al. Liquid crystalline properties of dissymmetric molecules IV. The substituent effect on thermal properties of nematic and smectic a phases in three aromatic ring systems with ester linkages. Liq Cryst [Internet]. 2000;27(9):1195–1205. doi: 10.1080/02678290050122042
   Web of Science ®Google Scholar
• Dewar MJS, Schroeder JP. P-alkoxy- and p-carbalkoxybenzoates of diphenols. A new series of liquid crystalline compounds1. J Org Chem [Internet]. 1965;30(7):2296–2300. doi: 10.1021/jo01018a042
   Web of Science ®Google Scholar
• Date RW, Imrie CT, Luckhurst GR, et al. Smectogenic dimeric liquid crystals. The preparation and properties of the α,ω-bis(4-n-alkylanilinebenzylidine-4′-oxy)alkanes. Liq Cryst [Internet]. 1992;12(2):203–238. doi: 10.1080/02678299208030393
   Web of Science ®Google Scholar
• Dennington R, Keith TA, Millam JM. GaussView 6.0. 16. Shawnee Mission. (KS): Semichem Inc; 2016. p. 143–150.
   Google Scholar
• Frisch MJ, Trucks GW, Schlegel HB, et al. G16_C01. 2016. p. Gaussian 16, Revision C.01, Gaussian, Inc. Wallin.
   Google Scholar
• Saccone M, Pfletscher M, Kather S, et al. Improving the mesomorphic behaviour of supramolecular liquid crystals by resonance-assisted hydrogen bonding. J Mater Chem C [Internet]. 2019;7:8643–8648. doi: 10.1039/C9TC02787D
   Web of Science ®Google Scholar
• Katariya K, Soni R, Nakum KJ, et al. New symmetric/unsymmetrical self-assembling salicylaldimine-chalcones: synthesis, photophysical study and DFT approach. J Mol Struct [Internet]. 2024;1295:136610. doi: 10.1016/j.molstruc.2023.136610
   Web of Science ®Google Scholar
• Katariya KD, Nakum KJ, Soni H, et al. Imine based four-ring chalcone-ester liquid crystals: synthesis, characterization, mesomorphic behaviour and DFT approach. J Mol Liq [Internet]. 2023;380:121719. doi: 10.1016/j.molliq.2023.121719
   Web of Science ®Google Scholar
• Akbari Z, Stagno C, Iraci N, et al. Biological evaluation, DFT, MEP, HOMO-LUMO analysis and ensemble docking studies of Zn(II) complexes of bidentate and tetradentate Schiff base ligands as antileukemia agents. J Mol Struct [Internet]. 2024;1301:137400. doi: 10.1016/j.molstruc.2023.137400
   Web of Science ®Google Scholar