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Isophlorins: Molecules at the Crossroads of Porphyrin and Annulene Chemistry
Author(s) -
Pohl Michael,
Schmickler Hans,
Lex Johann,
Vogel Emanuel
Publication year - 1991
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199116931
Subject(s) - annulene , dication , porphyrin , chemistry , molecule , connection (principal bundle) , stereochemistry , computational chemistry , photochemistry , organic chemistry , mathematics , geometry
The isophlorins already discussed by Woodward in connection with chlorophyll synthesis are Janus‐faced—on one hand porphyrins ( N , N ′‐dihydroporphyrins) and on the other true annulenes ([20] annulenes not conforming to the Hückel rule)—and as such are structurally particularly interesting. Whereas isophlorins not substituted at NH have evaded discovery and synthesis, the N , N ′, N ″, N ″′‐tetramethyloctaethylisophlorin ( 1 , RCH 3 ) has been prepared by two‐electron reduction of the known N , N ′, N ″, N ″′‐tetramethyloctaethylporphyrin dication.