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Synthesis, molecular structure and optical properties of glycidyl derivatives of quercetin

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Abstract

Synthesis of glycidyl ethers of quercetin and studies of their structure and spectral properties have been carried out. Using FTIR spectroscopy, 1H and HSQC NMR spectroscopy, mass spectrometry and quantum chemical simulations, it was shown that glycidation of 7-hydroxy and 4′-hydroxy groups primarily takes place, and then, the sequential glycidation of 3′-hydroxy and, further, 3-hydroxy groups occurs. Solvatochromic effects and quadratic polarizability of the obtained ethers—7,4′-diglycidyloxy-3,5,3′-trihydroxyflavone, 7,3′,4′-triglycidyloxy-5,3′-dihydroxyflavone and 3,7,3′,4′-tetraglycidyloxy-5-hydroxyflavone—were studied. It was shown that the diglycidyl and triglycidyl ethers can be used for creation of new polymeric NLO materials.

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Acknowledgments

The authors gratefully acknowledge Professor J. Błażejowski and Professor K. Krzymiński from University of Gdansk for assistance with testing the structures of the glycidyl ethers. The Ukrainian-American Laboratory of Computational Chemistry (UALCC, Kharkiv, Ukraine) is also gratefully acknowledged.

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Authors and Affiliations

  1. National Technical University «Kharkiv Polytechnic Institute», 21, Frunze Str., Kharkiv, 61002, Ukraine

    Dmitry A. Mishurov & Andrey A. Voronkin

  2. Institute of Chemistry, V.N. Karazin Kharkiv National University, 4, Svoboda Square, Kharkiv, 61022, Ukraine

    Alexander D. Roshal

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  1. Dmitry A. Mishurov
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  3. Alexander D. Roshal
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Correspondence to Alexander D. Roshal.

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Mishurov, D.A., Voronkin, A.A. & Roshal, A.D. Synthesis, molecular structure and optical properties of glycidyl derivatives of quercetin. Struct Chem 27, 285–294 (2016). https://doi.org/10.1007/s11224-015-0694-5

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