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Coumarin-Pyrazole Hybrid with Red Shifted ESIPT Emission and AIE Characteristics - a Comprehensive Study

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Abstract

The newly synthesized three coumarin pyrazole hybrid excited state intramolecular proton transfer (ESIPT) dyes show efficient charge transfer from the pyrazole ring and the coumarin towards the electron withdrawing dicyanovinylene group as revealed from the frontier molecular orbitals. Aggregation induced emission enhancement (AIEE) studies with 2-((3-(4-hydroxy-2-oxo-2H-chromen-3-yl)-1-phenyl-1H-pyrazol-4-yl)methylene) malononitrile showed 9 fold increase in the emission enhancement in 90% DMF-H2O mixture. Lippert-Mataga theory explained the solvatochromic behavior of the dyes in various solvents. The charge transfer characteristics and non-linear optical (NLO) properties have been supported and correlated with bond length alternation, bond order alternation and vibrational spectrum. As values of bond order alternation (BOA) tend to be more towards negative and as the value of α increases β decreases while the values of γ depends on the values of α and β. The observed values of γ are positive which revealed that β contributes significantly. The dyes exhibit linear and NLO properties superior to urea. (E)-2-(3-(2-(3-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-1-phenyl-1H-pyrazol-4-yl)vinyl)-5,5-dimethylcyclohex-2-en-1-ylidene) malononitrile shows enhanced linear and non-linear properties among the three dyes.

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Acknowledgements

Milind R. Shreykar is greatly thankful to University Grant Commission (U.G.C) and Technical Education Quality Improvement Programme (TEQIP), India for providing financial support.

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  1. Department of Dyestuff Technology, Institute of Chemical Technology, Nathalal Parekh Marg, Matunga, Mumbai, 400019, India

    Milind R. Shreykar & Nagaiyan Sekar

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  1. Milind R. Shreykar
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  2. Nagaiyan Sekar
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Correspondence to Nagaiyan Sekar.

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Shreykar, M.R., Sekar, N. Coumarin-Pyrazole Hybrid with Red Shifted ESIPT Emission and AIE Characteristics - a Comprehensive Study. J Fluoresc 27, 1687–1707 (2017). https://doi.org/10.1007/s10895-017-2106-2

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