Synthesis of novel styryl derivatives from 4-chloro-2-(morpholin-4-yl)-1,3-thiazole-5-carbaldehyde, study of their photophysical properties and TD-DFT computations

Sekar, Nagaiyan; Umape, Prashant G.; Padalkar, Vikas S.; Tayade, Rajratna P.; Ramasami, Ponnadurai

doi:10.1016/j.jlumin.2014.01.060

Cited by 10 publications

(1 citation statement)

References 64 publications

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“…Among the various luminous low-molecular-weight organic molecules that have been discovered [1] many contain the thiazole ring system (Scheme 1). [2][3][4] Imidazoles, oxazoles, and thiazoles are monocyclic 1,3-azole motifs that could be exploited to create luminous compounds such as chemosensors. [5][6][7] Monocyclic 1,3-azoles, distinct condensed azoles, have a degree of flexibility.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of (tricyanofuran‐3‐ylmethylene)hydrazinyl thiazole‐containing chromophore: A study of its photophysical properties, solvatochromism, and TD‐DFT computations

et al. 2022

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The chromophore 2-2- (3-cyano-5,5-dimethyl-4-((2-[thiazol-2-yl]hydrazono)methyl)furan-2(5H)-ylidene)malononitrile (TzHTCF) was prepared by diazo-coupling of diazotized 2-aminothiazole with 3-cyano-2-(dicyanomethylene)-4,5,5-trimethylfuran (TCF). The TzHTCF absorption solvatochromism, in different polarity solvents, demonstrated a ΔE max = +4.74 in which the positive sign implied the occurrence of a red shift and the TzHTCF lowest excited state was more polar than its ground state. In addition, the TzHTCF fluorescence spectrum produced a λ em in the 416-670 nm range and was more dependent on the solvent polarity than the absorption λ max , despite both exhibiting a red shift of 24 and 254 nm, respectively. To discover the Stokes shift (ΔνÞ behaviour of the TzHTCF derivative, Lippert-Mataga and linear solvation-energy relationship (LSER) formulations were utilized in which the LSER approach displayed better results than the Lippert-Mataga method (R 2 = 0.9931).Furthermore, the LSER showed that the absorption and fluorescence solvatochromic behaviours were dependent on the solvent's hydrogen-bond donor (α) and acceptor (β), along with the solvent's polarizability (π*). Moreover, DFT calculations showed that TzHTCF has a planar configuration and its simulated absorption and emission spectra in dimethyl sulphoxide revealed that λ max primarily originated from the HOMO!LUMO and HOMO-1!LUMO transitions, respectively.

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Section: Introductionmentioning

confidence: 99%

Synthesis of (tricyanofuran‐3‐ylmethylene)hydrazinyl thiazole‐containing chromophore: A study of its photophysical properties, solvatochromism, and TD‐DFT computations

et al. 2022

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Spectroscopic and nonlinear optical properties of new chalcone fluorescent probes for bioimaging applications: a theoretical and experimental study

et al. 2016

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In this study, the newly synthesized non-centrosymmetric, 4-dimethylamino-3'-isothiocyanatochalcone (PKA) compound was presented. This compound belongs to the chalcone group, and its main purpose is to be used in biomedical imaging as a fluorescence dye. For this reason, the linear and nonlinear properties in solvents of different polarity were thoroughly studied. In accordance with the requirements for a fluorochrome, the PKA compound is characterized by strong absorption, large Stokes' shifts, relatively high fluorescence quantum yields and high nonlinear optical response. Moreover, the isothiocyanate reactive probe was conjugated with Concanavalin A. Conventional fluorescence microscopy imaging of Candida albicans cells incubated with the PKA-Concanavalin A, is presented. The results of this study show that the novel conjugate PKA-Concanavalin A could be a promising new probe for cellular labelling in biological and biomedical research. Graphical abstract Spectroscopic behavior of the PKA dye.

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Fluorescent Styryl Dyes from 4-Chloro-2-(Diphenylamino)-1, 3-Thiazole-5-Carbaldehyde—Synthesis, Optical Properties and TDDFT Computations

2015

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4-Chloro-2-(diphenylamino)-1,3-thiazole-5-carbaldehyde was reacted with an active methylene compounds, cyanomethyl benzimidazole, cyanomethyl benzothiazole, barbituric acid and Meldrum's acid under Knoevenagel conditions to give novel push-pull styryl chromophores 8a-8d. The synthesized styryl chromophores were characterized by FT-IR, Mass and (1)H NMR spectral analysis. The photophysical characteristics of these styryl chromophores were evaluated. The effect of solvent polarity and viscosity on the absorption and emission properties of these chromophores was studied. The structural, molecular, electronic and photophysical parameters of the push-pull dyes were studied by using density functional theory (DFT) and time dependent density functional theory (TDDFT) computations. The ratio of the ground to the excited state dipole moment of the synthesized novel styryl dyes were calculated by Bakhshiev and Bilot-Kawski correlations.

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Synthesis of novel styryl derivatives from 4-chloro-2-(morpholin-4-yl)-1,3-thiazole-5-carbaldehyde, study of their photophysical properties and TD-DFT computations

Cited by 10 publications

References 64 publications

Synthesis of (tricyanofuran‐3‐ylmethylene)hydrazinyl thiazole‐containing chromophore: A study of its photophysical properties, solvatochromism, and TD‐DFT computations

Synthesis of (tricyanofuran‐3‐ylmethylene)hydrazinyl thiazole‐containing chromophore: A study of its photophysical properties, solvatochromism, and TD‐DFT computations

Spectroscopic and nonlinear optical properties of new chalcone fluorescent probes for bioimaging applications: a theoretical and experimental study

Fluorescent Styryl Dyes from 4-Chloro-2-(Diphenylamino)-1, 3-Thiazole-5-Carbaldehyde—Synthesis, Optical Properties and TDDFT Computations

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