A theoretical study of the photophysical properties of coumarin-carbohydrazone and coumarin-thiocarbohydrazone

Anamika, 2018, Advances in synthesis and potentially bioactive of coumarin derivatives, Curr. Org. Chem., 22, 2509, 10.2174/1385272822666181029102140 Keni, 2015, Recent progress in the drug development of coumarin derivatives as potent antituberculosis agents, Eur. J. Med. Chem., 100, 257, 10.1016/j.ejmech.2015.06.017 Wang, 2013, Cassia cinnamon as a source of coumarin in cinnamon-flavored food and food supplements in the United States, J. Agric. Food Chem., 61, 4470, 10.1021/jf4005862 Iemsam-Arng, 2016, Modified NLC-loaded coumarin for pharmaceutical applications: the improvement of physical stability and controlled release profile, Pharm. Dev. Technol., 21, 1015, 10.3109/10837450.2015.1089897 Stiefel, 2017, Bioprofiling of cosmetics with focus on streamlined coumarin analysis, ACS Omega, 2, 5242, 10.1021/acsomega.7b00562 Thakur, 2015, Coumarins as anticancer agents: A review on synthetic strategies, mechanism of action and SAR studies, Eur. J. Med. Chem., 101, 476, 10.1016/j.ejmech.2015.07.010 Decottignies, 2007, Characterisation of odour masking agents often used in the solid waste industry for odour abatement, Water Sci. Technol., 55, 359, 10.2166/wst.2007.198 Feuster, 2003, Detection of amines and unprotected amino acids in aqueous conditions by formation of highly fluorescent iminium ions, J. Am. Chem. Soc., 125, 16174, 10.1021/ja036434m Ray, 2008, A coumarin-derived fluorescence probe selective for magnesium, Inorg. Chem., 47, 2252, 10.1021/ic702388z Kielesinski, 2019, The synthesis and photophysical properties of tris-coumarins, PCCP, 21, 8314, 10.1039/C9CP00978G Wang, 2018, The coumarin conjugate: synthesis, photophysical properties and the ratiometric fluorescence response to water content of organic solvent, Dyes Pigments, 151, 233, 10.1016/j.dyepig.2018.01.004 Bhalekar, 2019, Coumarin and hydroxyl decorated viscosity sensitive triphenylamine derivatives: Synthesis, photophysical properties, viscosity sensitivity, TD-DFT, and NLO Properties, Chemistryselect, 4, 12512, 10.1002/slct.201903247 Pramod, 2019, Synthesis, photophysical, quantum chemical investigation, linear and non-linear optical properties of coumarin derivative: Optoelectronic and optical limiting application, Spectrochim. Acta A, 223, 10.1016/j.saa.2019.117288 Sun, 2019, New Coumarin-benzoxazole derivatives: Synthesis, photophysical and NLO properties, Dyes Pigments, 164, 287, 10.1016/j.dyepig.2019.01.010 Mantulin, 1973, Excited states of skin-sensitizing coumarins and psoralens. Spectroscopic studies, J. Am. Chem. Soc., 95, 5122, 10.1021/ja00797a004 Cao, 2019, Coumarin-based small-molecule fluorescent chemosensors, Chem. Rev., 119, 10403, 10.1021/acs.chemrev.9b00145 Ma, 2007, Coumarin-based fluorescent sensors, Prog. Chem., 19, 1258 Sanap, 2012, Synthesis of coumarin based fluorescent compounds, Tetrahedron Lett., 53, 5407, 10.1016/j.tetlet.2012.07.111 Mahapatra, 2016, Highly selective ratiometric fluorescent probes for detection of perborate based on excited-state intramolecular proton transfer (ESIPT) in environmental samples and living cells, Chemistryselect, 1, 375, 10.1002/slct.201500032 Yan, 2018, A novel turn-on fluorescent probe based on coumarin schiff's base for multichannel monitoring of Al3+, Hg2+ and ClO- in different solutions and its applications, Chemistryselect, 3, 10157, 10.1002/slct.201802228 Rajasekhar, 2017, Aβ plaque-selective NIR fluorescence probe to differentiate Alzheimer's disease from tauopathies, Biosens. Bioelectron., 98, 54, 10.1016/j.bios.2017.06.030 Dai, 2014, A simple and effective coumarin-based fluorescent probe for cysteine, Biosens. Bioelectron., 59, 35, 10.1016/j.bios.2014.03.018 Lee, 2006, Synthesis and anti-angiogenesis activity of coumarin derivatives, Bioorg. Med. Chem. Lett., 16, 4596, 10.1016/j.bmcl.2006.06.007 Fischer, 1995, Fluorescence of coumarins and xanthenes after two-photon absorption with a pulsed titanium-sapphire laser, Appl. Opt., 34, 1989, 10.1364/AO.34.001989 Qin, 2016, A small-molecule and resumable two-photon fluorescent probe for Zn2+ based on a coumarin Schiff-base, Sens. Actuator. B-Chem., 228, 156, 10.1016/j.snb.2016.01.031 Zheng, 2014, A unique carbazole-coumarin fused two-photon platform: development of a robust two-photon fluorescent probe for imaging carbon monoxide in living tissues, Chem. Sci., 5, 3439, 10.1039/C4SC00283K Genco, 2018, Bright polariton coumarin-based OLEDs operating in the ultrastrong coupling regime, Adv. Opt. Mater., 6, 1800364, 10.1002/adom.201800364 Lee, 2004, Efficient green coumarin dopants for organic light-emitting devices, Org. Lett., 6, 1241, 10.1021/ol049903d Yu, 2009, Synthesis, characterization and high-efficiency blue electroluminescence based on coumarin derivatives of 7-diethylamino-coumarin-3-carboxamide, Org. Electron., 10, 653, 10.1016/j.orgel.2009.02.026 Vekariya, 2017, Coumarin based sensitizers with ortho-halides substituted phenylene spacer for dye sensitized solar cells, Org. Electron., 48, 291, 10.1016/j.orgel.2017.06.013 Venkatraman, 2015, Artificial evolution of coumarin dyes for dye sensitized solar cells, PCCP, 17, 27672, 10.1039/C5CP04624F Wang, 2007, A high-light-harvesting-efficiency coumarin dye for stable dye-sensitized solar cells, Adv. Mater., 19, 1138, 10.1002/adma.200601020 Wu, 2017, Fluorescent chemosensors: the past, present and future, Chem. Soc. Rev., 46, 7105, 10.1039/C7CS00240H He, 2016, Fluorescent chemosensors manipulated by dual/triple interplaying sensing mechanisms, Chem. Soc. Rev., 45, 6449, 10.1039/C6CS00413J Sakai, 2017, Polyacetylenes as colorimetric and fluorescent chemosensor for anions, Polym. Rev., 57, 159, 10.1080/15583724.2016.1144613 Gale, 2018, Fluorescent and colorimetric sensors for anionic species, Coordin. Chem. Rev., 354, 2, 10.1016/j.ccr.2017.05.003 Samanta, 2019, Unambiguous detection of elevated levels of hypochlorous acid in double transgenic AD mouse brain, ACS Chem. Neurosci., 10, 4847, 10.1021/acschemneuro.9b00554 Rajasekhar, 2016, A high affinity red fluorescence and colorimetric probe for amyloid β aggregates, Sci. Rep., 6, 23668, 10.1038/srep23668 Narayanaswamy, 2014, A thiazole coumarin (TC) turn-on fluorescence probe for AT-base pair detection and multipurpose applications in different biological systems, Sci. Rep., 4, 6476, 10.1038/srep06476 Maity, 2011, Highly selective colorimetric chemosensor for Co2+, Inorg. Chem., 50, 11282, 10.1021/ic2015447 Biswas, 2016, Simple and efficient coumarin-based colorimetric and fluorescent chemosensor for F- detection: An ON1-OFF-ON2 fluorescent assay, Sens. Actuator. B-Chem., 222, 823, 10.1016/j.snb.2015.08.090 Ma, 2012, Bis-coumarins bridged by thiocarbazide as novel fluorescent sensor for Fe3+, Adv. Mater. Res.-Switz., 396–398, 2137 Day, 2005, TDDFT study of one- and two-photon absorption properties: Donor-pi-acceptor chromophores, J. Phys. Chem. B, 109, 1803, 10.1021/jp047511i Hua, 2016, High quantum yield and pH sensitive fluorescence dyes based on coumarin derivatives: fluorescence characteristics and theoretical study, RSC Adv., 6, 49221, 10.1039/C6RA05996A Zhang, 2017, A theoretical investigation of the two-photon absorption and fluorescent properties of coumarin-based derivatives for Pd2+ detection, RSC Adv., 7, 49505, 10.1039/C7RA08832A Ben Azaza, 2018, Synthesis and spectral properties of coumarins derivatives fluorescence emitters: Experiment and DFT/TDDFT calculations, Opt. Mater., 83, 138, 10.1016/j.optmat.2018.05.082 Liu, 2017, Altering intra- to inter-molecular hydrogen bonding by dimethylsulfoxide: A TDDFT study of charge transfer for coumarin 343, Spectrochim. Acta A, 177, 1, 10.1016/j.saa.2017.01.022 Pedone, 2013, Understanding the photophysical properties of coumarin-based Pluronic-silica (PluS) nanoparticles by means of time-resolved emission spectroscopy and accurate TDDFT/stochastic calculations, PCCP, 15, 12360, 10.1039/c3cp51943k M.J. Frisch, G.W. Trucks, H.B. Schlegel, et al., Gaussian 16 Rev. B.01, Wallingford, CT, 2016. Lee, 1988, Development of the colle-salvetti correlation-energy formula into a functional of the electron-density, Phys. Rev. B, 37, 785, 10.1103/PhysRevB.37.785 Becke, 1993, Density-functional thermochemistry.3. The role of exact exchange, J. Chem. Phys., 98, 5648, 10.1063/1.464913 Perdew, 1996, Generalized gradient approximation made simple, Phys. Rev. Lett., 77, 3865, 10.1103/PhysRevLett.77.3865 Adamo, 1999, Toward reliable density functional methods without adjustable parameters: The PBE0 model, J. Chem. Phys., 110, 6158, 10.1063/1.478522 Ernzerhof, 1999, Assessment of the Perdew–Burke–Ernzerhof exchange-correlation functional, J. Chem. Phys., 110, 5029, 10.1063/1.478401 Zhao, 2008, Theor. Chem. Acc., 120, 215, 10.1007/s00214-007-0310-x Yanai, 2004, A new hybrid exchange–correlation functional using the Coulomb-attenuating method (CAM-B3LYP), Chem. Phys. Lett., 393, 51, 10.1016/j.cplett.2004.06.011 Scalmani, 2010, Continuous surface charge polarizable continuum models of solvation. I. General formalism, J. Chem. Phys., 132, 10.1063/1.3359469 Lu, 2012, Multiwfn: A multifunctional wavefunction analyzer, J. Comput. Chem., 33, 580, 10.1002/jcc.22885 Ji, 2009, Tuning the intramolecular charge transfer of alkynylpyrenes: Effect on photophysical properties and its application in design of OFF−ON fluorescent thiol probes, J. Org. Chem., 74, 4855, 10.1021/jo900588e Zhao, 2007, Site-selective photoinduced electron transfer from alcoholic solvents to the chromophore facilitated by hydrogen bonding: A new fluorescence quenching mechanism, J. Phys. Chem. B, 111, 8940, 10.1021/jp0734530 Song, 2012, TD-DFT study on the excited-state proton transfer in the fluoride sensing of a turn-off type fluorescent chemosensor based on anthracene derivatives, Spectrochim. Acta A, 97, 746, 10.1016/j.saa.2012.07.010 Cheng, 2009, Synthesis of conjugated polymers for organic solar cell applications, Chem. Rev., 109, 5868, 10.1021/cr900182s