title: A combined theoretical and experimental investigation on the solvatochromism of ESIPT3-(1,3-benzothiazol-2-yl)-2-hydroxynaphthalene-1-carbaldehyde.
abstract: Excited state intramolecular proton transfer inspired 3-(1,3-benzothiazol-2-yl)-2-hydroxynaphthalene-1-carbaldehyde, showing solid state fluorescence has been synthesized. Existence of excited state intramolecular proton transfer process between carbonyl group and phenolic OH group has been theoretically predicted using computational method. Density functional theory and time dependent density functional theory computations have been used to investigate structural parameters and understand the photophysical properties of the synthesized carbaldehyde. The photophysical properties of carbaldehyde were evaluated using UV-Visible and fluorescence spectroscopy and are found to be very sensitive to the microenvironment such as solvent polarity and pH. The experimental absorption-emission a results are correlated with the computed values. The increase in the dipole moment of A2-Keto(*) than A2-Enol(*) suggested the presence of keto form in the excited state and which is responsible for the single fluorescence emission with a large Stokes shift in all solvents.
authors.affiliation: Tinctorial Chemistry Group, Department of Dyestuff Technology, Institute of Chemical Technology, Matunga, Mumbai 400 019, India.
authors.forename: Manjaree A
authors.initials: MA
authors.lastname: Satam
authors.affiliation: Tinctorial Chemistry Group, Department of Dyestuff Technology, Institute of Chemical Technology, Matunga, Mumbai 400 019, India.
authors.forename: Rahul D
authors.initials: RD
authors.lastname: Telore
authors.affiliation: Tinctorial Chemistry Group, Department of Dyestuff Technology, Institute of Chemical Technology, Matunga, Mumbai 400 019, India.
authors.forename: Abhinav B
authors.initials: AB
authors.lastname: Tathe
authors.affiliation: Tinctorial Chemistry Group, Department of Dyestuff Technology, Institute of Chemical Technology, Matunga, Mumbai 400 019, India.
authors.forename: Vinod D
authors.initials: VD
authors.lastname: Gupta
authors.affiliation: Tinctorial Chemistry Group, Department of Dyestuff Technology, Institute of Chemical Technology, Matunga, Mumbai 400 019, India. Electronic address: n.sekar@ictmumbai.edu.in.
authors.forename: Nagaiyan
authors.initials: N
authors.lastname: Sekar
mesh_terms: D003198:Computer Simulation; D006863:Hydrogen-Ion Concentration; D008956:Models, Chemical; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
chemical_list: D009281:Naphthalenes
keywords: Density functional theory; Dipole moment calculation; ESIPT; Photophysical property; Solid state fluorescence; Solvatochromism