Photooxidation and reproduction of pentacene derivatives substituted by aromatic groups
2007; Elsevier BV; Volume: 63; Issue: 39 Linguagem: Inglês
10.1016/j.tet.2007.07.021
ISSN1464-5416
AutoresKatsuhiko Ono, Hiroaki Totani, Takao Hiei, Akihiro Yoshino, Katsuhiro Saito, K. Eguchi, Masaaki Tomura, Jun‐ichi Nishida, Yoshiro Yamashita,
Tópico(s)Luminescence and Fluorescent Materials
ResumoPentacene derivatives substituted by aromatic groups at the 6,13-positions were prepared and investigated for their electronic properties and the photoaddition reaction with oxygen. The pentacene derivatives substituted by 2-thienyl and phenyl groups reacted with oxygen in solution under light and afforded their endoperoxides. These first-order kinetic constants were evaluated to be 1.5×10−3 s−1 and 2.7×10−3 s−1. The pentacene derivative with pentafluorophenyl groups was relatively stable in solution. The thermolysis and photolysis of the endoperoxide with 2-thienyl groups in solution afforded the pentacene derivative with yields of 30 and 44%, respectively. In addition, UV irradiation (254 nm) of the thin film of the endoperoxide was studied, which indicated the reproduction of the pentacene derivative.
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