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Luminescence feature of new 3,6‐di(thiazolidin‐5‐one‐2‐yl)‐carbazole derivative: synthesis, photophysical properties, density functional theory studies, and crystal shape effect
Author(s) -
Bawazeer Tahani M.,
Althagafi Ismail,
Morad Moataz,
Munshi Alaa M.,
Bayazeed Abrar A.,
Alharbi Arwa,
ElMetwaly Nashwa
Publication year - 2021
Publication title -
luminescence
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.428
H-Index - 45
eISSN - 1522-7243
pISSN - 1522-7235
DOI - 10.1002/bio.4013
Subject(s) - stokes shift , chemistry , density functional theory , intramolecular force , molecular orbital , carbazole , time dependent density functional theory , photochemistry , absorption spectroscopy , solvatochromism , homo/lumo , crystal (programming language) , absorption (acoustics) , hypsochromic shift , solvent , crystallography , luminescence , fluorescence , computational chemistry , molecule , materials science , stereochemistry , organic chemistry , physics , optoelectronics , quantum mechanics , computer science , composite material , programming language
A new carbazole chromophore conjugated with substituted thiazolidine‐4‐one ( CzPT ) was synthesized by applying the Knoevenagel reaction between 3,6‐diformyl‐ N ‐hexylcarbazole and ethyl 2‐aceto‐2‐(5‐oxo‐3‐phenylthiazolidin‐2‐ylidene)acetate. The chemical structure of the new derivative (CzPT) was elucidated by spectral studies. The CzPT absorption spectra in different solvents exhibited a red shift for λ max by increasing solvent polarity. Bands at 430–474 nm appeared and were attributed to intramolecular charge transfer with high π–π* characteristics. CzPT fluorescence spectra exhibited a red shift after increasing the solvent polarity. To understand the Stokes' shift ( ∆ ν ¯ ) behaviour of the CzPT derivative referring to the polarity of solvents, Lippert–Mataga and linear solvation‐energy relationship (LSER) models were employed in which the LSER exhibited respectable results compared with Lippert–Mataga ( r 2 = 0.9707). Moreover, time‐dependent density functional theory absorption spectra in hexane and dimethylformamide showed that λ max had a major contribution in the highest occupied molecular orbital to lowest unoccupied molecular orbital transition in both solvents. In addition, the reduced uniformity of crystal features may lead to dislocation or anomalous arrangement of crystals with irregular spacing, which automatically enhances the optical properties of such crystals.