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Novel Rhodafluors: Synthesis, Photophysical, pH and TD-DFT Studies

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Abstract

An efficient protocol for the synthesis of new rhodol derivatives has been developed. The synthesis involves condensation of 2-hydroxy benzophenone derivatives with 1, 3-dihydroxy benzene derivatives in solvents such as ionic liquid (N-methyl-2-pyrrolidonium hydrogen sulfate) and methane sulphonic acid. Both ionic liquid and methane sulphonic acid were found to be promising self-catalyzed solvents to bring out the conversion to form desired rhodols in excellent yields. In N-methyl-2-pyrrolidonium hydrogen sulfate reaction proceeds faster compared to methane sulphonic acid. The new fluorophores are investigated for their photophysical properties in various microenvironments and systematically characterized by means of density functional theory and time dependent density functional theory. Photophysical properties of the new rhodafluors found sensitive towards change in the pH of media and thus can be used as efficient pH sensors.

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Acknowledgments

One of the authors, KGT, is thankful to the Council of Scientific and Insdustrial Research (CSIR), India for Junior and Senior Research Fellowships, and RM is thankful to University Grant Comission for Junior and Senior Research Fellowships under SAP programme. SP is thankful to TEQIP (Technical Education Quality Improvement Program) for financial support.

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Authors and Affiliations

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

    Supriya S. Patil, Kishor G. Thorat, Ramnath Mallah & Nagaiyan Sekar

Authors
  1. Supriya S. Patil
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  2. Kishor G. Thorat
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  3. Ramnath Mallah
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  4. Nagaiyan Sekar
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Corresponding author

Correspondence to Nagaiyan Sekar.

Additional information

Supriya S. Patil and Kishor G. Thorat contributed equally equally to this work.

Electronic supplementary material

[Supporting Information contains optimized geometry parameter table, absorption emission spectra, 1H, 13C and LCMS spectra, etc.]

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Patil, S.S., Thorat, K.G., Mallah, R. et al. Novel Rhodafluors: Synthesis, Photophysical, pH and TD-DFT Studies. J Fluoresc 26, 2187–2197 (2016). https://doi.org/10.1007/s10895-016-1915-z

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