Synthesis of Carbazole-Based Selenaporphyrin <i>via</i> Annulation

Abstract

Cu(I)-mediated alkoxylation of doubly 1,3-butadiyne-bridged carbazole dimer <b>1</b>, followed by acid-catalyzed cyclization, provided furan-bridged carbazole dimer <b>3</b>, while annulation reaction of <b>1</b> with selenium in the presence of hydrazine monohydrate provided selenophene-bridged carbazole dimer <b>5a</b>. Oxidation of isophlorin <b>5a</b> afforded carbazole-based selenaporphyrin <b>5b</b>, which possessed distinct aromaticity and produced intensified and red-shifted absorption bands in the near-IR region