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Paper | Regular issue | Vol 89, No. 10, 2014, pp.2346-2355
Published online, 2nd October, 2014
DOI: 10.3987/COM-14-13080
Stepwise Syntheses of 3,6-Carbazole-Based Conjugated Oligomers

Hiroyuki Fujita and Tsuyoshi Michinobu*

*Department of Organic and Polymeric Materials, Graduate School of Science and Technology, Tokyo Institute of Technology, O-okayama 2-12-1, Muguro-ku, Tokyo 152-8552, Japan

Abstract

A series of monodispersed ethynylene-linked 3,6-carbazole oligomers was synthesized by the Sonogashira coupling and deprotection protocol. The resulting conjugated carbazole oligomers were characterized by 1H-, 13C-NMR, and IR spectroscopies, and MALDI-TOF mass spectrometry. The effective conjugation length of the 3,6-carbazole structure was evaluated from the longest wavelength absorption maxima (λmax) in CH2Cl2. The λmax gradually red-shifted with the increasing carbazole unit, and this bathochromic shift saturated at the pentamer.