Comparative studies of excited state intramolecular proton transfer (ESIPT) and azo-hydrazone tautomerism in naphthalene-based fluorescent acid azo dyes by computational study
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Suvidha Shinde
Abstract
We found that benzothiazole is responsible for enhancing fastness properties of dyes. On comparing the total electronic energies of naphthol tautomers (−1425.16 eV) and its analogs (−2146.59 eV), we found that benzothiazolyl series is more stable than the naphthol series. Frontier Molecular Orbitals (FMOs) also show flow of charge transfer from the donor to the acceptor in benzothiazole-containing compounds, whereas it is absent in plane naphthol series. Among the benzothiazolyl isomers, the hydrazone form is found to be more stable and responsible for fluorescence possession. Highest Occupied Molecular Orbital (HOMO)–Lowest Occupied Molecular Orbital (LUMO) energy band gap also indicates the same. Electrophilicity index and hyper-hardness values of both the series were found to be positive which directly ratifies photostability and reactivity. Benzothiazolyl series was found to be more stable, hence light fastness, enhanced.
Funding source: University Grants Commission
Award Identifier / Grant number: UGC CAS SAP
Acknowledgments
Suvidha S. Shinde is thankful to University Grant Commission, New Delhi, India for providing research UGC-SAP fellowship.
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Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Research funding: This research was supported by University Grant Commission (UGC CAS SAP).
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Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
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© 2020 Walter de Gruyter GmbH, Berlin/Boston
Articles in the same Issue
- Frontmatter
- Reviews
- Comparative studies of excited state intramolecular proton transfer (ESIPT) and azo-hydrazone tautomerism in naphthalene-based fluorescent acid azo dyes by computational study
- The application of the natural killer cells, macrophages and dendritic cells in treating various types of cancer
- Selection of oxypeucedanin as a potential antagonist from molecular docking analysis of HSP90
- Modeling and assessment of the transfer effectiveness in integrated bioreactor with membrane separation
- Modelling of enzyme kinetics: cellulose enzymatic hydrolysis case
- Synthesis, characterization and computational studies of 1,3-bis[( E)-furan-2-yl)methylene]urea and 1,3-bis[( E)-furan-2-yl)methylene]thiourea
Articles in the same Issue
- Frontmatter
- Reviews
- Comparative studies of excited state intramolecular proton transfer (ESIPT) and azo-hydrazone tautomerism in naphthalene-based fluorescent acid azo dyes by computational study
- The application of the natural killer cells, macrophages and dendritic cells in treating various types of cancer
- Selection of oxypeucedanin as a potential antagonist from molecular docking analysis of HSP90
- Modeling and assessment of the transfer effectiveness in integrated bioreactor with membrane separation
- Modelling of enzyme kinetics: cellulose enzymatic hydrolysis case
- Synthesis, characterization and computational studies of 1,3-bis[( E)-furan-2-yl)methylene]urea and 1,3-bis[( E)-furan-2-yl)methylene]thiourea
