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Cover Picture: Angew. Chem. Int. Ed. 8/2002
Author(s) -
Seidel Daniel,
Lynch Vincent,
Sessler Jonathan L.
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20020415)41:8<1255::aid-anie1255>3.0.co;2-c
Subject(s) - pyrrole , protonation , chemistry , porphyrin , molecule , aqueous solution , ion , crystallography , photochemistry , stereochemistry , organic chemistry
The cover picture shows the simple, one‐step synthesis of cyclo[8]pyrroles, a new class of aromatic heteroannulene. Using a newly developed biphasic oxidative coupling procedure that employs aqueous FeCl 3 as the oxidant, these novel porphyrin‐like systems may be obtained in yields exceeding 70% starting from well‐known bipyrrolic precursors. While formally derived from porphyrin as the result of substituting a pyrrole for each of the original bridging meso ‐carbon atoms, the cyclo[8]pyrroles differ from these quintessential tetrapyrrolic macroycles by virtue of Q‐like absorption bands that are red‐shifted into the near IR. Cyclo[8]pyrroles also show a propensity for protonation and anion binding that is underscored by the X‐ray structure of the sulfate salt that makes up the background for this illustration. More on these exciting new molecules can be found in the communication by J. L. Sessler et al. on pp. 1422–1425.