Triphenylamine and N-phenyl carbazole-based coumarin derivatives: Synthesis, solvatochromism, acidochromism, linear and nonlinear optical properties

[Display omitted] •Rigidified triphenylamine and N-phenyl carbazole based solvatochromic and acidochromic D-π-A coumarins.•Lippert-Mataga, Mac-Rae, and multilinear Kamlet-Taft and Catalan analysis corroborate ICT.•Solvatochromic NLO properties and comparison with DFT computed values using B3LYP, BHH...

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Bibliographic Details
Published in:Journal of photochemistry and photobiology. A, Chemistry. Chemistry., 2019-09, Vol.382, p.111937, Article 111937
Main Authors: Yadav, Sagar B., Kothavale, Shantaram, Sekar, Nagaiyan
Format: Article
Language:English
Subjects:
Acidochromism
Carbazole
Carbazoles
Charge transfer
Computer applications
Coumarin
Density functional theory
Dyes
Electrostatic properties
Molecular orbitals
NLOphoric coumarin
Nonlinear optics
Optical properties
Polarizability
Positive solvatochromism
Regression analysis
Solvatochromic NLO
Synthesis
TD-DFT
Time dependence
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Summary:[Display omitted] •Rigidified triphenylamine and N-phenyl carbazole based solvatochromic and acidochromic D-π-A coumarins.•Lippert-Mataga, Mac-Rae, and multilinear Kamlet-Taft and Catalan analysis corroborate ICT.•Solvatochromic NLO properties and comparison with DFT computed values using B3LYP, BHHLYP, and CAM-B3LYP. In a sequential study of rigidification of donating unit on its charge transfer towards accepting a coumarin unit, four donor-acceptor triphenylamine and N-phenyl carbazole based coumarin dyes were synthesized and characterized. The dyes exhibit positive solvatochromism which is well supported by linear as well as multilinear regression analysis. The intramolecular charge transfer characteristics were established using Generalized Mulliken-Hush (GMH), and frontier molecular orbital (FMO), Molecular electrostatic potential (MEP) plot analysis from optimized geometry. The detailed investigation of positive acidochromism is performed. The non-linear optical (NLO) properties of synthesized dyes were studied using solvatochromic and computational method. The linear polarizability, hyperpolarizability and second-order hyperpolarizability of the synthesized dyes were studied by time-dependent density functional theory computational method using three different functionals with the basis set 6–31 G (d).
ISSN:1010-6030
1873-2666
DOI:10.1016/j.jphotochem.2019.111937