The synthesis and one- and two-photon optical properties of dipolar, quadrupolar and octupolar donor-acceptor molecules containing dimesitylboryl groups

Jonathan C. Collings, Suk Yue Poon, Céline Le Droumaguet, Marina Charlot, Claudine Katan, Lars Olof Pålsson, Andrew Beeby, Jackie A. Mosely, Hanns Martin Kaiser, Dieter Kaufmann, Wai Yeung Wong, Mireille Blanchard-Desce, Todd B. Marder

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169 Citations (Scopus)

Abstract

Two series of related donor-acceptor conjugated dipolar, pseudoquadrupolar (V-shaped) and octupolar molecular systems based on the p- dimesitylborylphenylethynylaniline core, namely, 4-(4- dimesitylborylphenylethynyl)-N,N-dimethylaniline, 4-[4-(4- dimesitylborylphenylethynyl)phenylethynyl]-N,N-dimethylaniline, 3,6-bis(4-dimesitylborylphenylethynyl)-N-n-butylcarbazole and tris[4-(4-dimesitylborylphenylethynyl)phenyl]amine, and on the E-p-dimesityiborylethenylaniline motif, namely, E-4-dimesitylborylethenyl-N,N- di(4-tolyl)aniline, 3,6-bis(E-dimesitylborylethenyl)-N-n-butylcarbazole and tris(E-4-dimesitylborylethenylphenyl)amine have been synthesised by palladium-catalyzed cross-coupling and hydroboration routes, respectively. Their absorption and emission maxima, fluorescence lifetimes and quantum yields have been obtained and their two-photon absorption (TPA) spectra and TPA cross-sections have been examined. Of these systems, the octupolar compound tris(E-4-dimesitylborylethenylphenyl)amine has been shown to exhibit the largest TPA cross-section among the two series of approximately 1000 GM at 740 nm. Its TPA performance is comparable to those of other triphenylamine-based octupoles of similar size. The combination of such large TPA cross-sections and high emission quantum yields, up to 0.94, make these systems attractive for applications involving two-photon excited fluorescence (TPEF).

Original languageEnglish
Pages (from-to)198-208
Number of pages11
JournalChemistry - A European Journal
Volume15
Issue number1
DOIs
Publication statusPublished - 2009

Bibliographical note

Copyright:
Copyright 2009 Elsevier B.V., All rights reserved.

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