Synthesis of Carbazole-Containing Porphyrinoids by a Multiple An nidation Strategy: A Core-Modified and π-Expanded Porphyrin

摘要

Porphyrins are the most important pyrrolic macrocycles in light of their biological importance and ability to serve as efficient catalysts and functional pigments. Most porphyrins and porphyrinoids have been synthesized by the acid-catalyzed condensation of pyrroles and aldehydes, or their equivalents. The exception are those in which the pyrrole rings are connected either directly or through vinylene linkages, and these have been synthesized by the oxidative coupling of pyrroles and McMurry coupling reactions. New synthetic protocols for porphyrins are desirable, since they may allow the more efficient preparation of porphyrins or the exploration of structurally unique porphyrins that are otherwise very difficult to prepare. Carbazole-based materials have been extensively studied in view of their highly emissive and electron-conducting properties, chemical stabilities, and compatibilities with various transformations such as polymerizations and metal-catalyzed cross-coupling reactions. Despite these developments, porphyrins containing carbazole moieties have rarely been explored.