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Substituent Modulation from ESIPT to ICT Emission in Benzoimidazolphenyl-methanones Derivatives: Synthesis, Photophysical and DFT Study

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Abstract

Design and synthesis of five new derivatives of benzophenone based imidazole dyes is presented. Synthesized dyes were well characterized by 1H NMR, 13C NMR, FT-IR and mass analysis. Dyes contain a secondary acceptor, ESIPT core and different donors forming (D-ESIPT core-A) as basic skeleton in order to study both ESIPT and ICT systematically in this same class of dyes. Dyes without a donor substituent showed ESIPT emission while dyes with a substituted strong donor showed intramolecular charge transfer (ICT) emission. Moreover emission properties of methoxy analogue dyes has been studied to further confirm non-ESIPT emission in dyes without donors and ICT emission in strong donor substituted dyes. All dyes exhibited long range emissions from 392 to 567 nm. Dyes exhibiting ESIPT emission showed negative solvatochromism while ICT emission exhibiting dyes shows positive solvatochromism. ICT and ESIPT characteristics are well correlated with polarity functions plots and Mulliken–Hush analysis. Experimental observations are well supported by TD–DFT and computed energies. The electrophilicity index has been calculated to get details of the stabilities of possible tautomers.

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Acknowledgements

The authors are greatly thankful to Indoco Remedies Pvt. Ltd. for recording the mass spectra of the dyes. One of the authors, Amol G. Jadhav, is greatful to UGC for financial support.

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  1. Department of Intermediate and Dyestuff Technology, Institute of Chemical Technology (Formerly UDCT), N.P. Marg, Matunga, Mumbai, 400 019, Maharashtra, India

    Amol G. Jadhav & Nagaiyan Sekar

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Correspondence to Nagaiyan Sekar.

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Jadhav, A.G., Sekar, N. Substituent Modulation from ESIPT to ICT Emission in Benzoimidazolphenyl-methanones Derivatives: Synthesis, Photophysical and DFT Study. J Solution Chem 46, 777–797 (2017). https://doi.org/10.1007/s10953-017-0602-2

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