Preparation, spectral and thermal properties of new Isoflavone derivatives: mesomorphic properties and DFT studies

References

• Hertz E, Lavorel B, Faucher O. A simple molecular gas sample can be used to achieve ultrafast optical buffering in two-dimensional optical imaging, thus serving as a promising extension of the well-developed liquid-crystal display technology. Nature Photonics. 2011;5:78–79.
   Web of Science ®Google Scholar
• Ollis WD.The isoflavonoids In: Geissman TA, editors. The chemistry of flavanoid compounds. New York, NY: Oxford, Pergamon Press; 1962. p. 353.
   Google Scholar
• Cagniant P, Cagniant D. Recent advances in the chemistry of benzo[b]furan and its derivatives. Part I: occurrence and synthesis. Adv Heterocy Chem. 1975;18:337–482.
   Google Scholar
• Grotewold E. (The science of flavonoids) Department of cellular and molecular biology. columbus, Ohio 43210, USA: the Ohio state university. 2006.
   Google Scholar
• Dowling S, Regan F, Hughes H. The characterisation of structural and antioxidant properties of isoflavone metal chelates. J Inorg Biochem. 2010;104:1091–1098.
   PubMed Web of Science ®Google Scholar
• Aldercreutz H, Fotsis T, Bannwart C, et al. Determination of urinary lignans and phytoestrogen metabolites, potential antiestrogens and anticarcinogens, in urine of women on various habitual diets. J Steroid Biochem. 1986;25:791–797.
   PubMedGoogle Scholar
• Boland GM, Donelly DMX. Isoflavonoids and related compounds. Nat Prod Rep. 1998;15:241260.
   Web of Science ®Google Scholar
• Goodby JW, Gortz V, Cowling SJ, et al. Thermotropic liquid crystalline glycolipids. Chem Soc Rev. 2007;36:1971–2032.
   PubMed Web of Science ®Google Scholar
• Wei P, Liu M, Chen Y, et al. Asian Pacific. Systematic review of soy isoflavone supplements on osteoporosis in women. J Trop Med. 2012;5:243–248.
   Web of Science ®Google Scholar
• Zhang EJ, Ng KM, Luo KQ. Extraction and purification of isoflavones from soybeans and characterization of their estrogenic activities. J Agric Food Chem. 2007;55:6940–6950.
   PubMed Web of Science ®Google Scholar
• Wang Q, Ge X, Tian X, et al. Soy isoflavone: the multipurpose phytochemical. Biomed Rep. 2013;1:697–701.
   PubMedGoogle Scholar
• Srinivasa HT, Harishkumar HN, Palakshamurthy BS. New coumarin carboxylates having trifluoromethyl, diethylamino and morpholino terminal groups: synthesis and mesomorphic characterizations. J Mol Struc. 2017;1131:97–102.
   Web of Science ®Google Scholar
• Mahadevan KM, Harishkumar HN, Jagadeesh NM, et al. Synthesis and liquid crystal property of new fluoro coumarin carboxylates. Mol Cryst Liq Cryst. 2013;570:20–35.
   Web of Science ®Google Scholar
• Srinivasa HT, Palakshamurthy BS, Mohammad ATK. Ethyl 7-hydroxycoumarin-3- carboxylate derivatives: synthesis, characterization and effect of liquid crystal properties. J Mol Struc. 2018;1155:513–519.
   Web of Science ®Google Scholar
• Paul MK, Singh YD, Dey A, et al. Coumarin based emissive rod shaped new schiff base mesogens and their zinc(II) complexes: synthesis, photophysical, mesomorphism, gelation and DFT studies. Liq Cryst. 2016;43(3):343–360.
   Web of Science ®Google Scholar
• Cavero E, Serrano JL, Gimenez R, et al. Liquid crystalline dendrimers based on cinnamates and coumarins. Liq Cryst. 2016;43(10):1408–1421.
   Web of Science ®Google Scholar
• Zhang H-Y, Cui J, Zhang Y, et al. Isoflavone and prostate cancer: a review of some critical issues. Chin Med J. 2016;129:341–347.
   PubMed Web of Science ®Google Scholar
• Hirose T, Tsuya T, Nishigaki T, et al. Phase transitions of 6-(4-n-alkoxybenzoyloxy)- flavones and 3-cyano-7-(4-n-alkoxybenzoyloxy)-coumarins. Liq Cryst. 1989;4:653–659.
   Web of Science ®Google Scholar
• Timmons DJ, Jordan AJ, Kirchon AA, et al. Asymmetric flavone-based liquid crystals: synthesis and properties. Liq Cryst. 2017;44(9):1436–1449.
   Web of Science ®Google Scholar
• Goodby JW. Liquid-crystalline glycolipids: towards understanding the roles of liquid crystals in biological and life processes. Liq Cryst. 2006;33:1229–1237.
   Web of Science ®Google Scholar
• Yang ZL, Xu R, Ali-Rachedi F, et al. Liquid crystalline glycosteroids and acyl steroid glycosides (ASG). Liq Cryst. 2017;44(12–13):2089–2107.
   Web of Science ®Google Scholar
• Chudgar NK, Bosco R, Shah SN. Synthesis and characterization of 3-phenyl-4[H]-4- [one]-benzopyran (isoflavone) derivatives as potential mesogens. Liq Cryst. 1991;10:141–145.
   Web of Science ®Google Scholar
• Yeap G-Y, Yam W-S, Chang W-S, et al. Synthesis, anisotropic behaviour and structural changes in some para-substituted isoflavones: 4′-substituted-7-(4″-decyloxybenzoyloxy)- 4H-1-benzopyran-4-ones. Phase Transitions. 2011;84:256–268.
   Web of Science ®Google Scholar
• Belmar J, Parra M, Zuniga C, et al. Synthesis of new mesogenic compounds having the isoflavone core group. Liq Cryst. 1999;26:75–81.
   Web of Science ®Google Scholar
• Chan T-N, Lu Z, Yam W-S, et al. Non-symmetric liquid crystal dimers containing an isoflavone moiety. Liq Cryst. 2012;39:393–402.
   Web of Science ®Google Scholar
• Imrie CT, Henderson PA, Yeap G-Y. Liquid crystal oligomers: going beyond dimers. Liq Cryst. 2009;36(6–7):755–777.
   Web of Science ®Google Scholar
• Imrie CT, Henderson PA. Liquid crystal dimers and higher oligomers: between monomers and polymers. Chem Soc Rev. 2007;36(12):2096–2124.
   PubMed Web of Science ®Google Scholar
• Imrie CT, Henderson PA. Liquid crystal dimers and oligomers. Cur Opin Collo Interface Sci. 2002;7(5–6):298–311.
   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(1):68–83.
   Web of Science ®Google Scholar
• Paterson DA, Walker R, Abberley JP, et al. Azobenzene-based liquid crystal dimers and the twist-bend nematic phase. Liq Cryst. 2017;44(12–13):2060–2078.
   Web of Science ®Google Scholar
• Paterson DA, Abberley JP, Harrison WT, et al. Cyanobiphenyl-based liquid crystal dimers and the twist-bend nematic phase. Liq Cryst. 2017;44(1):127–146.
   Web of Science ®Google Scholar
• Mandle RJ, Stevens MP, Goodby JW. Developments in liquid-crystalline dimers and oligomers. Liq Cryst. 2017;44(12–13):2046–2059.
   Web of Science ®Google Scholar
• Archbold CT, Andrews JL, Mandle RJ, et al. Effect of the linking unit on the twist-bend nematic phase in liquid crystal dimers: a comparative study of two homologous series ofmethylene- and ether-linked dimers. Liq Cryst. 2017;44(1):84–92.
   Web of Science ®Google Scholar
• Yeap G-Y, Mohammad AKT, Osman H. Synthesis and anisotropic properties of novel asymmetric diones fused with 1,3-oxazepine and oxazepane rings. Mol Cryst Liq Cryst. 2012;552:177–193.
   Web of Science ®Google Scholar
• Mohammad AKT, Yeap G-Y, Osman H. Synthesis and mesomorphic behavior of new mesogenic compounds possessing a biphenyl ester moiety with a 6-amino-1,3- dimethyluracil. Mol Cryst Liq Cryst. 2014;590:130–139.
   Web of Science ®Google Scholar
• Mohammad AKT, Yeap G-Y, Osman H. Synthesis and phase transition studies of new dimer compounds connected to a 1,3-dimethylbarbituric acid core. Turk J Chem. 2014;38:443–453.
   Web of Science ®Google Scholar
• Mohammad AKT, Yeap G-Y, Osman H. Synthesis, characterization and theoretical study of a new liquid crystal compound with an oxazepine core. J Mol Struct. 2015;1087:88–96.
   Web of Science ®Google Scholar
• Mohammad AKT, Srinivasa HT, Tiong HS, et al. Synthesis and comparative studies of phase transition behaviour of new dimeric liquid crystals consisting of dimethyluracil and biphenyl cores. J Mol Liq. 2016;219:765–772.
   Web of Science ®Google Scholar
• Mohammad AKT, Srinivasa HT, Mohammed HM, et al. Synthesis mesomorphic and theoretical studies of some new unsymmetrical dimeric ethers of 6-amino-1,3-dimethyluracil and biphenyl cores. J Mol Struct.2016;1117:201–207.
   Web of Science ®Google Scholar
• Mohammad AKT, Srinivasa HT, Hariprasad S, et al. Enhanced liquid crystal properties in symmetric ethers containing the oxazepine core: synthesis and characterization of seven member heterocyclic dimers. Tetrahedron. 2016;72:3948–3957.
   Web of Science ®Google Scholar
• Mohammad AKT, Srinivasa HT, Hariprasad S, et al. New mesogenic compounds possessing a biphenyl ester and ether moiety comprising 1,3-dimethylbarbituric acid: synthesis, characterisation and mesomorphic studies. Liq Cryst. 2016;43:1174–1183.
   Web of Science ®Google Scholar
• Mohammad AKT, Srinivasa HT, Hariprasad S, et al. Novel oxazepinedione- derived symmetric dimers: synthesis and mesophase characterisation of seven-membered heterocyclic compounds. Liq Cryst. 2016;43:1739–1747.
   Web of Science ®Google Scholar
• Ivsic T, Baumeister U, Dokli I, et al. Sensitivity of the N-TB phase formation to the molecular structure of imino-linked dimers. Liq Cryst. 2017;44(1):93–105.
   Web of Science ®Google Scholar
• Dawood AA, Grossel MC, Luckhurst GR, et al. On the twist-bend nematic phase formeddirectly from the isotropic phase. Liq Cryst. 2016;43(1):2–12.
   Web of Science ®Google Scholar
• Siddaiah V, Rao CV, Venkateswarlu S, et al. A concise synthesis of polyhydroxydihydrochalcones and homoisoflavonoids. Tetrahedron. 2006;62:841–846.
   Web of Science ®Google Scholar
• Liu J, Yang Z, Luo S, et al. Facile method for the large-scale synthesis of 6,7,4′- trihydroxyisoflavanone. Synth Commun. 2014;44:3296–3303.
   Web of Science ®Google Scholar
• Yam WS, Yeap G-Y. Nematogenic and smectogenic liquid crystals from new heterocyclic isoflavone derivatives: synthesis, characterization and X-ray diffraction studies. Chin Chem Lett. 2011;22:229–232.
   Web of Science ®Google Scholar
• Dawood AA, Grossel MC, Luckhurst GR, et al. Twist-bend nematics, liquid crystal dimers, structure-property relations. Liq Cryst. 2017;44(1):106–126.
   Web of Science ®Google Scholar
• Yeap G-Y, Yam W-S, Ito MM, et al. Synthesis and mesomorphic properties of 7-acyloxy-3-(4-acyloxyphenyl)-4H-1-benzopyran-4-one. Liq Cryst. 2007;34:649–654.
   Web of Science ®Google Scholar
• Balasubramanian S, Ward DL, Nair MG. The first isolation and crystal structure of a boron difluoro complex (isoflavone yellow). Biologically active intermediates produced during isoflavonesynthesis. J Chem Soc. 2000;1:567–569. Perkin Trans.
   Google Scholar
• Date RW, Imrie CT, Luckhurst GR, et al. Smectogenic dimeric liquid-crystals - thepreparation and properties of the alpha,omega-bis(4-normal-alkylanilinebenzylidine-4ʹ-oxy)alkanes. Liq Cryst. 1992;12(2):203–238.
   Web of Science ®Google Scholar
• Hogan JL, Imrie CT, Luckhurst GR. Asymmetric dimeric liquid-crystals - the preparation and properties of the alpha-(4-cyanobiphenyl-4ʹ-oxy)-omega-(4-normal- alkylanilinebenzylidene-4 ‘-oxy)hexanes. Liq Cryst. 1988;3(5):645–650.
   Web of Science ®Google Scholar
• Attard GS, Date RW, Imrie CT, et al. Nonsymmetrical dimeric liquid-crystals – the preparation and properties of the alpha-(4-cyanobiphenyl-4ʹ-yloxy)-omega-(4-n-alkylanilinebenzylidene-4ʹ-o xy)alkanes. Liq Cryst. 1994;16(4):529–581.
   Web of Science ®Google Scholar
• Imrie CT. Non-symmetric liquid crystal dimers: how to make molecules intercalate. Liq Cryst. 2006;33(11–12):1449–1485.
   Web of Science ®Google Scholar
• Imrie CT, Taylor L. The preparation and properties of low molar mass liquid-crystals possessing lateral alkyl chains. Liq Cryst. 1989;6(1):1–10.
   Web of Science ®Google Scholar
• Henderson PA, Seddon JM, Imrie CT. Methylene- and ether-linked liquid crystal dimers II. Effects of mesogenic linking unit and terminal chain length. Liq Cryst. 2005;32(11–12):1499–1513.
   Web of Science ®Google Scholar
• Henderson PA, Niemeyer O, Imrie CT. Methylene-linked liquid crystal dimers. Liq Cryst. 2001;28(3):463–472.
   Web of Science ®Google Scholar
• Lu Z, Henderson PA, Paterson BJA, et al. Liquid crystal dimers and the twist-bend nematic phase. The preparation and characterisation of the alpha,omega-bis(4-cyanobiphenyl-4 ‘-yl) alkanedioates. Liq Cryst. 2014;41(3):471–483.
   Web of Science ®Google Scholar
• Yeap G-Y, Ha ST, Lim P-L, et al. Synthesis and mesomorphic properties of schiff base esters ortho-hydroxy-para-alkyloxybenzylidene-para-substituted anilines. Mol Cryst Liq Cryst. 2004;423:73–84.
   Web of Science ®Google Scholar
• Rajasekhar Y, Karunakar M, Ragini D, et al. Synthesis, characterization and photophysical studies of rare earth metal complexes with a mesogenic Schiff-base. J Mol Liq. 2016;216:510–515.
   Web of Science ®Google Scholar
• Yeap G-Y, Ha S-T, Ito MM, et al. Synthesis, fourier transform infrared, 1D and 2D NMR spectral studies on the conformation of two new cholesteryl 4-alkoxyphenyl-4′ benzoates. J Mol Struct. 2004;687:57–64.
   Web of Science ®Google Scholar
• Stamatoiu O, Bubnov A, Tarcomnicul I, et al. Synthesis and spectral characterisation of new amido-ether Schiff bases. J Mol Struct. 2008;886:187–196.
   Web of Science ®Google Scholar
• Yeap G-Y, Ha S-T, Ishizawa N, et al. Synthesis, crystal structure and spectroscopic study of para substituted 2-hydroxy-3-methoxybenzalideneanilines. J Mol Struct. 2003;658:87–99.
   Web of Science ®Google Scholar
• Abraham S, Mallia VA, Ratheesh KV, et al. Reversible thermal and photochemical switching of liquid crystalline phases and luminescence in diphenylbutadiene-based mesogenic dimers. J Am Chem Soc. 2006;128:7692–7698.
   PubMed Web of Science ®Google Scholar
• Paterson DA, Gao M, Kim YK, 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(32):6827–6840.
   PubMed Web of Science ®Google Scholar