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NLOphoric Red Emitting Bis Coumarins with O-BF2-O core - Synthesis, Photophysical Properties and DFT Studies

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Abstract

The red emitting dyes were synthesized by employing coumarin core as a donor and boron-bonded coumarin as an acceptor. 7-(N,N-Diethylamino)-coumarin 3-aldehyde was reacted with 3-acetyl-4-hydroxy-coumarin, 7-(N,N-diethylamino)-3-acetyl-4-hydroxy-coumarin and 3-acetyl-4-hydroxy-1-methyl-quinolone to form the corresponding chalcones. The synthesized chalcones were though red shifted as compared to the parent coumarin, and were not emitting in red region. The BF2-complexation was used as a tool to introduce a red shift in the molecules. The BF2-complexes synthesized were found to be red emitting and show higher one photon absorption cross section. The solvatochromism shown by these dyes was studied in the light of solvent polarity parameters. DFT calculations were used to understand the photophysical properties of the synthesized dyes. NLO properties of the dyes were estimated by solvatochromic and computational methods. All the molecules synthesized were characterised with the HRMS and NMR spectral Analysis.

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Acknowledgments

Abhinav Tathe is thankful to University Grants Commission, New Delhi for providing senior research fellowship.

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  1. Tinctorial Chemistry Group, Department of Dyestuff Technology, Institute of Chemical Technology, N. P. Marg, Matunga, Mumbai, MH, India, 400019

    Abhinav B. Tathe & Nagaiyan Sekar

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Correspondence to Nagaiyan Sekar.

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Tathe, A.B., Sekar, N. NLOphoric Red Emitting Bis Coumarins with O-BF2-O core - Synthesis, Photophysical Properties and DFT Studies. J Fluoresc 26, 471–486 (2016). https://doi.org/10.1007/s10895-015-1733-8

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