title: Synthesis of carbazole-based hetero-core-modified porphyrins.
abstract: Cu(I)-mediated annulation reaction of a 1,1'-(1,3-butadiyne)-8,8'-(2,5-thiophene)-bridged carbazole dimer 10 with amines provided the N-substituted carbazole-based isophlorines 11a-11c. A similar annulation reaction with selenium in the presence of hydrazine monohydrate afforded hetero-core-modified isophlorine 12. The oxidation of 12 generated the corresponding 21-selena-23-thiaporphyrin 13, which exhibited NIR absorption. The intramolecular charge transfer from Se to S was confirmed by the (1)H NMR results along with DFT calculations.
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Chihiro
authors.initials: C
authors.lastname: Maeda
authors.forename: Motoki
authors.initials: M
authors.lastname: Masuda
authors.forename: Naoki
authors.initials: N
authors.lastname: Yoshioka