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Cyclo[8]pyrrole: A Simple‐to‐Make Expanded Porphyrin with No Meso Bridges
Author(s) -
Seidel Daniel,
Lynch Vincent,
Sessler Jonathan L.
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20020415)41:8<1422::aid-anie1422>3.0.co;2-o
Subject(s) - porphyrin , pyrrole , hydrogen bond , chemistry , crystal structure , crystallography , ion , stereochemistry , molecule , photochemistry , organic chemistry
Easily obtained in a single step from bipyrrolic precursors in yields over 70 %, cyclo[8]pyrroles represent a new class of porphyrin analogues that display the classic disklike structure of porphyrins. The X‐ray crystal structure of one of the cyclo[8]pyrroles obtained (see picture) shows that the macrocycle acts as a formal diprotonated receptor and forms eight hydrogen bonds to a sulfate ion bound within its core.