The Synthesis and One- and Two-Photon Optical Properties of Dipolar, Quadrupolar and Octupolar Donor-Acceptor Molecules Containing Dimesitylboryl Groups

被引:191
作者
Collings, Jonathan C. [3 ]
Poon, Suk-Yue [4 ,5 ]
Le Droumaguet, Celine [1 ]
Charlot, Marina [1 ]
Katan, Claudine [1 ]
Palsson, Lars-Olof [3 ]
Beeby, Andrew [3 ]
Mosely, Jackie A. [3 ]
Kaiser, Hanns Martin [2 ,3 ]
Kaufmann, Dieter [2 ]
Wong, Wai-Yeung [4 ,5 ]
Blanchard-Desce, Mireille [1 ]
Marder, Todd B. [3 ]
机构
[1] Univ Rennes 1, CNRS, CPM, F-35042 Rennes, France
[2] Tech Univ Clausthal, Inst Organ Chem, D-38678 Clausthal Zellerfeld, Germany
[3] Univ Durham, Dept Chem, Durham DH1 3LE, England
[4] Hong Kong Baptist Univ, Ctr Adv Luminescence Mat, Kowloon Tong, Hong Kong, Peoples R China
[5] Hong Kong Baptist Univ, Dept Chem, Kowloon Tong, Hong Kong, Peoples R China
关键词
boron; C-C coupling; hydroboration; luminescence; two-photon absorption; 3-COORDINATE ORGANOBORON COMPOUNDS; EXCITATION CROSS-SECTIONS; CHARGE-TRANSFER EMISSION; A-PI-A; PHOTOPHYSICAL PROPERTIES; TRIVALENT BORON; SINGLE-PHOTON; FLUORESCENCE EXCITATION; CRYSTAL-STRUCTURES; ORGANIC-MOLECULES;
D O I
10.1002/chem.200801719
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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).
引用
收藏
页码:198 / 208
页数:11
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