Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 34, Pages 10118-10121Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201604297
Keywords
isoporphyrins; macrocycles; NIR dyes; porphyrinoids; templated synthesis
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Zinc and cadmium complexes of meso-arylisoporphyrins carrying a pyrrolyl or dipyrrinyl substituent at the sp(3) carbon atom were obtained through a simple one-pot variation of the Alder-Longo porphyrin synthesis. Key to the formation and stabilization of isoporphyrins is the presence of metal acetates during the oxidative macrocyclization step. The characteristic Q-bands of isoporphyrins are found in the NIR region between 750 nm and 880 nm. All of the isolated pyrrolyl-and dipyrrinyl-appended isoporphyrins are stable under typical laboratory conditions and allow chemical transformations like BF2 coordination, transmetalation, and ligand exchange.
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