NOVEL FORMATION OF DIPYRROLO- AND DIINDOLO[1,2-a:2 ',1 '-c]QUINOXALINE DERIVATIVES AND THEIR OPTICAL PROPERTIES

作者：Matsumoto Shoji^*; Qu Sheng; Kobayashi Takamitsu; Kanehiro Masahiro; Akazome Motohiro; Ogura Katsuyuki

来源：Heterocycles, 2010, 80(1): 645-656.

DOI：10.3987/COM-09-S(S)51

• Dipyrrolo[1,2-a:2 ',1 '-c]quinoxaline
• Diindolo[1,2-a:2 ',1 '-c]quinoxaline
• Iodine-Induced Reaction
• UV-VIS Spectrum
• Fluorescence Spectrum

Dipyrrolo- and diindolo[1,2-a:2',1'-c]quinoxaline structures (A and B, respectively) were synthesized from 1,2-di(1-pyrrolyl)- and 1,2-di(1-indolyl)benzene derivatives with iodine using a novel intramolecular coupling reaction. Apparent differences between A and B were observed from UV-VIS absorption and fluorescence spectra. Sharp peaks with a fine structure were observed in the absorption and fluorescence spectra of diindolo[1,2-a:2',1'-c]quinoxaline (2b). Introduction of a phenyl ring at the 6 and 6' positions of the indole moieties of 2b is efficient for imparting a red shift. In addition, the electron-withdrawing group at those positions particularly affected the emission peaks.

• 出版日期2010-1-1