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Paper | Special issue | Vol 80, No. 2, 2010, pp. 1165 - 1175
Published online: 18th September, 2009
DOI: 10.3987/COM-09-S(S)98
Synthesis of Tetrabenzoporphyrins Fused with Fluoranthenes

Jun Nakamura, Tetsuo Okujima,* Yuya Tomimori, Naoki Komobuchi, Hiroko Yamada, Hidemitsu Uno, and Noboru Ono

*Department of Chemistry and Biology, Graduate School or Science and Engineering, Ehime University, Matsuyama 790-8577, Japan

Abstract

Tetrabenzoporphyrins fused with fluoranthenes were prepared by the retro Diels-Alder reaction of the precursors composed of a porphyrin and four fluoranthenes connected with bicyclo[2.2.2]octadiene (BCOD). These porphyrins exhibited the Soret (480–494 nm, ε = 243,000–277,000) and intense Q bands (739–760 nm, ε = 375,000–509,000). Free bases and Zn complexes of them fluoresce at 760 nm and 746 nm with small Storks shifts and high quantum yields of 30 and 10 %, respectively.

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