Syntheses of Novel Carbazolylacetylene-Derived Macrocycles

Abstract

The syntheses of novel cyclic oligomers based on the carbazolylacetylene unit are described. The desired cyclic tetramer could be synthesized in 14.3% yield by the reaction of 3,6-diethynyl-9-tetradecylcarbazole and 3,6-bis(3’-iodo-9’-tetradecylcarbazolyl)-9-tetradecylcarbazole in the presence of Pd(PPh3)4/CuI as catalysts under high dilution conditions and purified by column chromatography and isolated by preparative gel permeation chromatography. Besides the tetramer, a cyclic octamer was also isolated in 5.4% yield.