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Synthesis and Properties of Aryl- and Amino-Substituted Dibenzo[b,e]phosphindolizines
Akihiro Tsurusaki1, Makoto Nakamura1, Akihiro Komura1
1Department of Chemistry, Graduate School of Science, Osaka Metropolitan University, 3-3-138 Sugimoto, Sumiyoshi-ku, Osaka, 558-8585, Japan.
Abstract:
Dibenzo[b,e]phosphindolizine oxides with five different aryl groups and a diphenylamino group at the 10-position are synthesized by the Suzuki-Miyaura cross-coupling reaction and the Buchwald-Hartwig amination reaction of 10-chlorodibenzo[b,e]phosphindolizine. The molecular structures and properties of the products are elucidated by X-ray crystallographic analysis, UV-vis spectroscopy, and electrochemical analysis. Dibenzo[b,e]phosphindolizines with p-(diphenylamino)phenyl and diphenylamino groups have smaller HOMO-LUMO gaps and higher HOMO energy levels than derivatives with methoxy and trifluoromethyl groups and without an amino group. The substituent effects are also investigated by theoretical calculations.
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