The Synthesis and One- and Two-Photon Optical Properties of Dipolar, Quadrupolar and Octupolar Donor-Acceptor Molecules Containing Dimesitylboryl Groups
Résumé
Two series of related donor-acceptor conjugated dipolar, pseudo-quadrupolar (V-shaped) and octupolar molecular systems based on the p-dimesitylborylphenylethynylaniline, namely 4-(4-dimesitylborylphenylethynyl)-N,N-dimethylaniline, 4-[4-(4-dimesitylboryl-phenylethynyl)phenylethynyl]-N,N-dimethylaniline, 4,4'-bis(4-dimesitylborylphenyl-ethynyl)-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, 4,4'-bis(E-dimesitylborylethenyl)-N-n-butylcarbazole and tris(E-4-dimesitylborylethenylphenyl)amine have been synthesized, 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 spectra and two-photon absorption (TPA) cross-sections have been examined. Of these systems, the octupolar compound tris-(E-4-dimesitylborylethenylphenyl)amine has been shown to exhibit by far the largest two-photon absorption cross-section among the two series and amount to about 1000 GM at 740 nm. Its TPA performance is comparable to those of other triphenylamine based octupoles of similar size.
Domaines
Chimie théorique et/ou physique
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