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Red Emitting Monoazo Disperse Dyes with Phenyl(1H-benzoimidazol-5-yl) Methanone as Inbuilt Photostabilizing Unit: Synthesis, Spectroscopic, Dyeing and DFT Studies

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Abstract

Synthesis of three novel phenyl(1H-benzoimidazol-5-yl)methanone based fluorescent monoazo disperse dyes and their characterization by spectroscopic methods (1H NMR, 13C NMR, IR and MS) are presented. Insertion of phenyl(1H-benzoimidazol-5-yl)methanone moiety bring about induced fluorescence properties and enhanced photostability as compared to the previously reported analogues (CI Solvent Yellow 14, 4-diethylamino-2-hydroxy-1-diazobenzene and 7-(diethylamino)-4-hydroxy-3-(phenyldiazenyl)-2H-chromen-2-one). Synthesized phenyl(1H-benzoimidazol-5-yl)methanone based dyes exhibited red-shifted absorption maxima (497–516 nm), high molar extinction coefficients and are emitting in the far-red region (565–627 nm). Moreover, naphthalene-comprising dyes showed negative solvatochromism while N,N-diethylamine comprising dyes showed positive solvatochromism and are in good agreement with solvent polarity graphs and the computed energy levels of highest occupied and lowest unoccupied molecular orbitals. Synthesised dyes have better photostability (light fastness) and sublimation fastness on dyed polyester and nylon compared to reported analogues. DFT calculated energies, electrophilicity index and Frontier Molecular Orbitals (FMO’s) enabled to evaluate the stabilities of azo and hydrazone forms of the dyes.

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Acknowledgements

One of the author Amol G. Jadhav is thankful to UGC for financial assistance in terms of SRF.

Suvidha Shinde is thankful to the Centre of Advanced Studies (UGC) for JRF and SRF under the Special Assistance Programme (SAP).

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  1. Amol G. Jadhav and Suvidha S. Shinde contributed equally to this work.

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  1. Department of Dyestuff Technology, Institute of Chemical Technology, Nathalal Parekh Marg, Matunga, Mumbai, 400 019, India

    Amol G. Jadhav, Suvidha S. Shinde & Nagaiyan Sekar

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  1. Amol G. Jadhav
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Correspondence to Nagaiyan Sekar.

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Jadhav, A.G., Shinde, S.S. & Sekar, N. Red Emitting Monoazo Disperse Dyes with Phenyl(1H-benzoimidazol-5-yl) Methanone as Inbuilt Photostabilizing Unit: Synthesis, Spectroscopic, Dyeing and DFT Studies. J Fluoresc 28, 639–653 (2018). https://doi.org/10.1007/s10895-018-2226-3

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