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Synthesis, structure, and properties of luminescent diazaborole and indole systems

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Chemistry of Heterocyclic Compounds Aims and scope

Thiophenes and phenylacetylenes, decorated with 1-methylindol-2-yl, 1,3,2-benzodiazaborol-2-yl, 1,3,2-diazaborol-2-yl, or 1,3,2-diazaborolidinyl groups at one end and dimesitylborolyl or CN substituents at the opposite end of the molecules, were synthesized. Upon UV irradiation, these push-pull systems in THF solution gave rise to bright-blue emission with Stokes shifts ranging from 4100 to 9300 cm–1 and quantum efficiencies up to 0.99. Thereby intramolecular charge transfer took place from the HOMO of the indolyl or borolyl fluorophores to the LUMO, mainly centered on the electron-withdrawing cyano or dimesitylboranyl group.

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  1. Fakultät für Chemie der Universität Bielefeld, Universitätsstraße 25, D-33615, Bielefeld, Germany

    Lothar Weber, Daniel Eickhoff, Hans-Georg Stammler & Beate Neumann

  2. Equipe Chimie Physique, IPREM, UMR 5254, Université de Pau et des Pays de l’Adour, 2 Av. du président Angot, B.P. 1155, 64013, Pau Cedex, France

    Anna Chrostowska & Clovis Darrigan

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(1), 54–65

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Weber, L., Eickhoff, D., Chrostowska, A. et al. Synthesis, structure, and properties of luminescent diazaborole and indole systems. Chem Heterocycl Comp 53, 54–65 (2017). https://doi.org/10.1007/s10593-017-2021-0

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