Synthesis of carbazole-based selenaporphyrin via annulation.
Cu(I)-mediated alkoxylation of doubly 1,3-butadiyne-bridged carbazole dimer 1, followed by acid-catalyzed cyclization, provided furan-bridged carbazole dimer 3, while annulation reaction of 1 with selenium in the presence of hydrazine monohydrate provided selenophene-bridged carbazole dimer 5a. Oxidation of isophlorin 5a afforded carbazole-based selenaporphyrin 5b, which possessed distinct aromaticity and produced intensified and red-shifted absorption bands in the near-IR region.
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Yokohama 223-8522, Japan.
Motoki
M
Masuda
Chihiro
C
Maeda
Naoki
N
Yoshioka
D002227:Carbazoles / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D007454:Iodides / Q000737:chemistry*; D008665:Metalloporphyrins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012643:Selenium / Q000737:chemistry*; D019265:Spectroscopy, Near-Infrared
D002227:Carbazoles; D007454:Iodides; D008665:Metalloporphyrins; D003300:Copper; C073870:cuprous iodide; D012643:Selenium