The Synthesis and One‐ and Two‐Photon Optical Properties of Dipolar,Quadrupolar and Octupolar Donor–Acceptor Molecules Containing Dimesitylboryl Groups |
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Authors: | Jonathan C Collings Dr Suk‐Yue Poon Dr Céline Le Droumaguet Dr Marina Charlot Dr Claudine Katan Dr Lars‐Olof Pålsson Dr Andrew Beeby Dr Jackie A Mosely Dr Hanns Martin Kaiser Dieter Kaufmann Prof Dr Wai‐Yeung Wong Prof Dr Mireille Blanchard‐Desce Dr Todd B Marder Prof Dr |
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Institution: | 1. Department of Chemistry, Durham University, South Road, Durham, DH1 3LE (UK), Fax: (+44)?191‐384‐4737;2. Department of Chemistry and Centre for Advanced Luminescence Materials, Hong Kong Baptist University,Waterloo Road, Kowloon Tong, Hong Kong (P.R. China), Fax: (+852)?3411‐7348;3. Université de Rennes 1, CNRS, Chimie et Photonique Moléculaires (CPM), Campus de Beaulieu Case 1003, 35042, Rennes Cedex (France), Fax: (+33)?22323‐6617;4. Institut für Organische Chemie der Technischen Universit?t Clausthal, Leibnizstr. 6, 38678, Clausthal‐Zellerfeld (Germany) |
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Abstract: | 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 tris4‐(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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Keywords: | boron C?C coupling hydroboration luminescence two‐photon absorption |
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