Coumarin based emissive rod shaped new schiff base mesogens and their zinc(II) complexes: synthesis, photophysical, mesomorphism, gelation and DFT studies

References

• Brun M-P, Bischoff L, Garbay C. A very short route to enantiomerically pure coumarin-bearing fluorescent amino acids. Angew Chem Int Ed. 2004;43:3432–3436. DOI:10.1002/anie.200454116.
   PubMed Web of Science ®Google Scholar
• Sun Y-F, Xu S-H, Wu R-T, et al. The synthesis, structure and photoluminescence of coumarin-based chromophores. Dyes and Pigments. 2010;87:109–118. DOI:10.1016/j.dyepig.2010.03.003.
   Web of Science ®Google Scholar
• Inagaki S, Ohtani O, Goto Y, et al. Light harvesting by a periodic mesoporous organosilica chromophore. Angew Chem Int Ed. 2009;48:4042–4046. DOI:10.1002/anie.200900266.
   PubMed Web of Science ®Google Scholar
• Ezeh VC, Harrop TC. A sensitive and selective fluorescence sensor for the detection of arsenic(III) in organic media. Inorg Chem. 2012;51:1213–1215. DOI:10.1021/ic2023715.
   PubMed Web of Science ®Google Scholar
• Halim M, Tremblay MS, Jockusch S, et al. Transposing molecular fluorescent switches into the near-IR: development of luminogenic reporter substrates for redox metabolism. J Am Chem Soc. 2007;129:7704–7705. DOI:10.1021/ja071311d.
   PubMed Web of Science ®Google Scholar
• Yeh J-T, Chen W-C, Liu S-R, et al. A coumarin-based sensitive and selective fluorescent sensor for copper(II) ions. New J Chem. 2014;38:4434–4439. DOI:10.1039/C4NJ00695J.
   Web of Science ®Google Scholar
• Jung HS, Ko KC, Kim G-H, et al. Coumarin-based thiol chemosensor: synthesis, turn-on mechanism, and its biological application. Org Lett. 2011;13:1498–1501. DOI:10.1021/ol2001864.
   PubMed Web of Science ®Google Scholar
• Schraub M, Soll S, Hampp N. High refractive index coumarin-based photorefractive polysiloxanes. Eur Polym J. 2013;49:1714–1721. DOI:10.1016/j.eurpolymj.2013.03.021.
   Web of Science ®Google Scholar
• Essaïdi Z, Krupka O, Iliopoulos K, et al. Synthesis and functionalization of coumarin-containing copolymers for second order optical nonlinearities. Opt Mater. 2013;35:576–581. DOI:10.1016/j.optmat.2012.10.011.
   Web of Science ®Google Scholar
• Sun Y-F, Wang H-P, Chen Z-Y, et al. Solid-state fluorescence emission and second-order nonlinear optical properties of coumarin-based fluorophores. J Fluoresc. 2013;23:123–130. DOI:10.1007/s10895-012-1125-2.
   PubMed Web of Science ®Google Scholar
• Trenor SR, Shultz AR, Love BJ, et al. Coumarins in polymers: from light harvesting to photo-cross-linkable tissue scaffolds. Chem Rev. 2004;104:3059–3078. DOI:10.1021/cr030037c.
   PubMed Web of Science ®Google Scholar
• Kim C, Trajkovska A, Wallace JU, et al. New insight into photoalignment of liquid crystals on coumarin-containing polymer films. Macromolecules. 2006;39:3817–3823. DOI:10.1021/ma060269o.
   Web of Science ®Google Scholar
• Kang H, Kwon K-S, Kang D, et al. Enhanced, perpendicular liquid-crystal alignment on rubbed films of a coumarin-containing polystyrene. Macromol Chem Physic. 2007;208:1853–1861. DOI:10.1002/macp.200700270.
   Web of Science ®Google Scholar
• Chigrinov G, Kozenkov VM, Kwok HS. Photoalignment of liquid crystalline materials: physics and application. England: John Wiley and Son Ltd.; 2008.
   Google Scholar
• He J, Zhao Y, Zhao Y. Photoinduced bending of a coumarin-containing supramolecular polymer. Soft Matter. 2009;5:308–310. DOI:10.1039/B814278E.
   Web of Science ®Google Scholar
• Kobatake S, Takami S, Muto H, et al. Rapid and reversible shape changes of molecular crystals on photoirradiation. Nature. 2007;446:778–781. DOI:10.1038/nature05669.
   PubMed Web of Science ®Google Scholar
• Kittapa MM, Harishkumar NH. Synthesis, fluorescence and liquid crystal properties of coumarins. Saarbrücken: Lambert Academic Publishing; 2012.
   Google Scholar
• Takechi H, Kubo K, Takahashi H, et al. Crystal structure, mesomorphic and emission properties of liquid crystals having a 7-(diethylamino)-3-phenylcoumarin Core. J Oleo Sci. 2007;56:195–200. DOI:10.5650/jos.56.195.
   PubMedGoogle Scholar
• Tian Y, Akiyama E, Nagase Y. Liquid crystalline cyclic tetramethyltetrasiloxanes containing coumarin moieties. J Mater Chem. 2003;13:1253–1258. DOI:10.1039/B302857G.
   Web of Science ®Google Scholar
• Mahadevan KM, Harishkumar HN, Masagalli JN, et al. Synthesis and liquid crystal property of new fluoro coumarin carboxylates. Mol Cryst Liq Cryst. 2013;570:20–35. DOI:10.1080/15421406.2012.704824.
   Web of Science ®Google Scholar
• Dave JS, Menon MR, Patel PR. Synthesis and mesomorphic characterization of azoesters with a coumarin ring. Liq Cryst. 2002;29:543–549. DOI:10.1080/02678290110114341.
   Web of Science ®Google Scholar
• Chen P, Li Y, Chen X, et al. Synthesis, mesomorphic and gelation properties of 7-alkoxycoumarin-3-carbonyl hydrazine. Liq Cryst. 2012;39:1393–1401. DOI:10.1080/02678292.2012.718377.
   Web of Science ®Google Scholar
• Nakai H, Takenaka S, Kusabayashi S. Thermal and dielectric properties of liquid crystals with a coumarin skeleton. Bull Chem Soc Jpn. 1983;56:3571–3377. DOI:10.1246/bcsj.56.3571.
   Web of Science ®Google Scholar
• Buchs J, Gäbler M, Janietz D, et al. Coumarin-based emissive liquid crystals. Liq Cryst. 2014;41:1605–1618. DOI:10.1080/02678292.2014.936530.
   Web of Science ®Google Scholar
• Morita Y, Ushijima H, Era K, et al. Synthesis and physico-chemical properties of polar liquid crystal materials incorporating a coumarin skeleton at the terminal position. Mol Cryst Liq Cryst. 2008;494:282–292. DOI:10.1080/15421400802430000.
   Web of Science ®Google Scholar
• Kumar V, Kumar A, Diwan U, et al. Zn2+-responsive highly sensitive fluorescent probe and 1D coordination polymer based on a coumarin platform. Dalton Trans. 2013;42:13078–13083. DOI:10.1039/C3DT51182K.
   PubMed 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. DOI:10.1080/15421400490436250.
   Web of Science ®Google Scholar
• Babu SS, Praveen VK, Ajayaghosh A. Functional π-gelators and their applications. Chem Rev. 2014;114:1973–2129. DOI:10.1021/cr400195e.
   PubMed Web of Science ®Google Scholar
• Zhang P, Wang H, Liu H, et al. Fluorescence-enhanced organogels and mesomorphic superstructure based on hydrazine derivatives. Langmuir. 2010;26:10183–10190. DOI:10.1021/la100325c.
   PubMed Web of Science ®Google Scholar
• Prabhu DD, Kumar NS, Sivadas AP, et al. Trigonal 1,3,4-oxadiazole-based blue emitting liquid crystals and gels. J Phys Chem B. 2012;116:13071–13080. DOI:10.1021/jp305349h.
   PubMed Web of Science ®Google Scholar
• Guha S, Lohar S, Bolte M, et al. Crystal structure and interaction of 6-amino coumarin with nitrite ion for its selective fluorescence detection. Spectrosc Lett. 2012;45:225–235. DOI:10.1080/00387010.2011.605416.
   Web of Science ®Google Scholar
• Lai CK, Chang C-H, Tsai C-H. Liquid crystalline properties of bis(salicylaldiminato)copper(II) complexes: the first columnar discotics derived from salicylaldimine Schiff bases. J Mater Chem. 1998;8:599–602. DOI:10.1039/A707091H.
   Web of Science ®Google Scholar
• Paul MK, Kalita G, Laskar AR, et al. Synthesis and mesomorphic behaviour of achiral four-ring unsymmetrical bent-core liquid crystals: nematic phases. J Mol Struct. 2013;1049:78–89. DOI:10.1016/j.molstruc.2013.06.044.
   Web of Science ®Google Scholar
• Hehre WJ, Radom L, Schleyer PR, et al. Ab initio molecular orbital theory. New York: Wiely; 1986.
   Google Scholar
• Becke AD. Density-functional thermochemistry. III. the role of exact exchange. J Chem Phys. 1993;98:5648–5652. DOI:10.1063/1.464913.
   Web of Science ®Google Scholar
• Lee C, Yang W, Parr RG. Development of the colle-salvetti correlation-energy formula into a functional of the electron density. Phys Rev B. 1988;37:785–789. DOI:10.1103/PhysRevB.37.785.
   Web of Science ®Google Scholar
• Miertus S, Tomasi J. Approximate evaluations of the electrostatic free energy and internal energy changes in solution processes. J Chem Phys. 1982;65:239–245. DOI:10.1016/0301-0104(82)85072-6.
   Web of Science ®Google Scholar
• Miertus S, Scrocco E, Tomasi J. Electrostatic interaction of a solute with a continuum. A direct utilizaion of AB initio molecular potentials for the prevision of solvent effects. J Chem Phys. 1981;55:117–129. DOI:10.1016/0301-0104(81)85090-2.
   Web of Science ®Google Scholar
• Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian 09, Revision B.01. Wallingford (CT): Gaussian, Inc.; 2010.
   Google Scholar
• Golcu A, Tumer M, Demirelli H, et al. Cd(II) and Cu(II) complexes of polydentate Schiff base ligands: synthesis, characterization, properties and biological activity. Inorg Chim Acta. 2005;358:1785–1797. DOI:10.1016/j.ica.2004.11.026.
   Web of Science ®Google Scholar
• Creaven BS, Devereux M, Karcz D, et al. Copper(II) complexes of coumarin-derived Schiff bases and their anti-Candida activity. J Inorg Biochem. 2009;103:1196–1203. DOI:10.1016/j.jinorgbio.2009.05.017.
   PubMed Web of Science ®Google Scholar
• Zhao L, Loy DA, Shea KJ. Photodeformable spherical hybrid nanoparticles. J Am Chem Soc. 2006;128:14250–14251. DOI:10.1021/ja066047n.
   PubMed Web of Science ®Google Scholar
• Majumder A, Rosair GM, Mallick A, et al. Synthesis, structures and fluorescence of nickel, zinc and cadmium complexes with the N,N,O-tridentate Schiff base N-2-pyridylmethylidene-2-hydroxy-phenylamine. Polyhedron. 2006;25:1753–1762. DOI:10.1016/j.poly.2005.11.029.
   Web of Science ®Google Scholar
• Abu-Eittah H, El-Tawil A. The electronic absorption spectra of some coumarins. A molecular orbital treatment. Can J Chem. 1985;63:1173–1179. DOI:10.1139/v85-200.
   Web of Science ®Google Scholar
• Joshi A, Manasreh MO, Davis EA, et al. Optical properties of colloidal InGaP∕ZnS core/shell nanocrystals. Appl Phys Lett. 2006;89:111907–3. DOI:10.1063/1.2354031.
   Web of Science ®Google Scholar
• Liuzzo V, Oberhauser W, Pucci A. Synthesis of new red photoluminescent Zn(II)-salicylaldiminato complex. Inorg Chem Commun. 2010;13:686–688. DOI:10.1016/j.inoche.2010.03.020.
   Web of Science ®Google Scholar
• Nijegorodov NI, Downey WS. The influence of planarity and rigidity on the absorption and fluorescence parameters and intersystem crossing rate constant in aromatic molecules. J Phys Chem. 1994;98:5639–5643. DOI:10.1021/j100073a011.
   Web of Science ®Google Scholar
• Martin A, Long C, Forster RJ, et al. Near IR emitting BODIPY fluorophores with mega-stokes shifts. Chem Commun. 2012;48:5617–5619. DOI:10.1039/C2CC31150J.
   PubMed Web of Science ®Google Scholar
• Su Z, Chen K, Guo Y, et al. A coumarin-based fluorescent chemosensor for Zn2+ in aqueous ethanol media. J Fluoresc. 2010;20:851–856. DOI:10.1007/s10895-010-0628-y.
   PubMed Web of Science ®Google Scholar
• Xue L, Li G, Yu C, et al. A ratiometric and targetable fluorescent sensor for quantification of mitochondrial zinc ions. Chem Eur J. 2012;18:1050–1054. DOI:10.1002/chem.201103007.
   PubMed Web of Science ®Google Scholar
• Jung HS, Ko KC, Lee JH, et al. Rationally designed fluorescence turn-on sensors: a new design strategy based on orbital control. Inorg Chem. 2010;49:8552–8557. DOI:10.1021/ic101165k.
   PubMed Web of Science ®Google Scholar
• Paul MK, Saha SK, Dilipkumar Singh Y, et al. Synthesis, mesomorphic, photophysical and computational studies of new achiral four-ring unsymmetrical bent-core mesogens and their Copper(II) complexes. Liq Cryst. 2014;41:1367–1381. DOI:10.1080/02678292.2014.920931.
   Web of Science ®Google Scholar
• Marcos M. Design and synthesis of low molecular weight metallomesogens. In: Serrano JL, editor. Metallomesogens: synthesis properties and applications. New York (NY): VCH Publisher; 1996. 235–299.
   Google Scholar
• George M, Weiss RG. Chemically reversible organogels via “Latent” gelators. aliphatic amines with carbon dioxide and their ammonium carbamates. Langmuir. 2002;18:7124–7135. DOI:10.1021/la0255424.
   Web of Science ®Google Scholar
• Kishida T, Fujita N, Hirata O, et al. Axial coordination changes the morphology of porphyrin assemblies in an organogel system. Org Biomol Chem. 2006;4:1902–1909. DOI:10.1039/B602025A.
   PubMed Web of Science ®Google Scholar
• Kryachko ES, Ludena EV. Energy density functional theory of many-electron system. Dordrecht: Kluwer; 1990.
   Google Scholar
• Koopmans TA. Über die Zuordnung von Wellenfunktionen und Eigenwerten zu den Einzelnen Elektronen Eines Atoms. Physica. 1933;1104. doi:10.1016/S0031-8914(34)90011-2
   Google Scholar
• Parr G, Chattaraj PK. Principle of maximum hardness. J Am Chem Soc. 1991;113:1854–1855. DOI:10.1021/ja00005a072.
   Web of Science ®Google Scholar
• Aihara J. Reduced HOMO−LUMO gap as an index of kinetic stability for polycyclic aromatic hydrocarbons. J Phys Chem. 1999;103:7487–7495. DOI:10.1021/jp990092i.
   Web of Science ®Google Scholar
• Chattaraj PK, Sengupta S. Popular electronic structure principles in a dynamical context. J Phys Chem. 1996;100:16126–16130. DOI:10.1021/jp961096f.
   Web of Science ®Google Scholar