Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 1, Pages 198-208Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200801719
Keywords
boron; C-C coupling; hydroboration; luminescence; two-photon absorption
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Funding
- UIC
- Hong Kong Research Grants Council [HKBU202106P]
- Hong Kong Baptist University [FRG/05-06/II-71]
- CNRS
- Rennes Metropole
- Engineering and Physical Sciences Research Council [EP/C508955/1] Funding Source: researchfish
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Two series of related donor-acceptor conjugated dipolar, pseudo-quadrupolar (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-dimesitylborylethenylaniline 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).
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