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Synthesis, spectral and photochemical properties of a biphotochromic dyad based on 3-styrylbenzo[f]quinoline and 2-[2-(pyren-1-yl)ethenyl]quinoline

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Abstract

A biphotochromic dyad, in which the styrylbenzo[f]quinoline (SBQ) and 2-[(2-(pyren-1-yl)ethenyl]quinoline (PEQ) moieties are linked to each other via an ester bridge, and the corresponding model monophotochromic compounds were synthesized. The investigation of the spectral and photochemical properties of the dyad and their comparison with the model compounds revealed efficient Förster resonance energy transfer (FRET), resulting in quenching of fluorescence and photoisomerization of the SBQ photochrome and sensitization of the same processes for the PEQ photochrome. Density functional theory calculations at the TD CAM-B3LYP/6-31G* level adequately reproduce the main features of the absorption spectra of the dyad as a biphotochromic system.

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Authors and Affiliations

  1. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432, Chernogolovka, Moscow Region, Russian Federation

    M. F. Budyka & V. M. Li

Authors
  1. M. F. Budyka
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  2. V. M. Li
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Correspondence to V. M. Li.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1665–1674, September, 2021.

The work was performed within the framework of the State assignment (No. AAAA-A19-119070790003-7) using facilities of the Multiple-User Analytical Center of the Institute of Problems of Chemical Physics of the Russian Academy of Sciences. The synthesis of methyl 2-((E)-2-pyren-1-yl-vinyl)quinoline-6-carboxylate was financially supported by the Ministry of Science and Higher Education of the Russian Federation (grant No. 075-15-2020-779).

This paper does not contain descriptions of studies on animals or humans.

The authors declare no competing interests.

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Budyka, M.F., Li, V.M. Synthesis, spectral and photochemical properties of a biphotochromic dyad based on 3-styrylbenzo[f]quinoline and 2-[2-(pyren-1-yl)ethenyl]quinoline. Russ Chem Bull 70, 1665–1674 (2021). https://doi.org/10.1007/s11172-021-3268-2

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  • DOI: https://doi.org/10.1007/s11172-021-3268-2

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