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Synthesis, Photo-physical and DFT Studies of ESIPT Inspired Novel 2-(2′,4′-Dihydroxyphenyl) Benzimidazole, Benzoxazole and Benzothiazole

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Abstract

Novel ESIPT inspired benzimidazole, benzoxazole and benzothiazole were synthesized from 2,4-dihydroxy benzoic acid and 1,2-phenelenediamine, 2-aminophenol, and 2-aminothiophenol respectively. The synthesized 2-(2′,4′-dihydroxyphenyl) benzimidazole, benzoxazole and benzothiazole are fluorescent and the emission characteristic are very sensitive to the micro-environment. They show a single absorption and dual emission with large Stokes shift originating from excited state intramolecular proton transfer. The absorption-emission characteristics of all these compounds are studied as a function of pH. The change in the electronic transition, energy levels, and orbital diagrams of synthesized compounds were investigated by the molecular orbital calculation and were correlated with the experimental spectral emission. Experimental absorption and emission wavelengths are in good agreement with those predicted using the Density Functional Theory (DFT) and Time-Dependent Density Functional Theory (TD-DFT) [B3LYP/6-31G(d)].

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Acknowledgments

Vikas Patil and Vikas Padalkar are thankful to the Institute of Chemical Technology, Mumbai, India.

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Authors and Affiliations

  1. Tinctorial Chemistry Group, Institute of Chemical Technology (Formerly UDCT), N. P. Marg, Matunga, Mumbai, 400 019, Maharashtra, India

    Vikas S. Patil, Vikas S. Padalkar, Abhinav B. Tathe, Vinod D. Gupta & N. Sekar

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  1. Vikas S. Patil
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  2. Vikas S. Padalkar
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  3. Abhinav B. Tathe
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Correspondence to N. Sekar.

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Patil, V.S., Padalkar, V.S., Tathe, A.B. et al. Synthesis, Photo-physical and DFT Studies of ESIPT Inspired Novel 2-(2′,4′-Dihydroxyphenyl) Benzimidazole, Benzoxazole and Benzothiazole. J Fluoresc 23, 1019–1029 (2013). https://doi.org/10.1007/s10895-013-1228-4

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