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Strong Induced‐Fit Binding of Viologen and Pyridine Derivatives in Adjustable Porphyrin Cavities
Author(s) -
Deutman Alexander B. C.,
Smits Jan M. M.,
de Gelder René,
Elemans Johannes A. A. W.,
Nolte Roeland J. M.,
Rowan Alan E.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201402919
Subject(s) - porphyrin , viologen , chemistry , pyridine , stereochemistry , photochemistry , combinatorial chemistry , medicinal chemistry
The synthesis and binding properties of new porphyrin cage compounds consisting of a rigid diphenylglycoluril part, which is connected via flexible bis(ethyleneoxy) spacers to a (metallo)porphyrin “roof”, are reported. Binding of viologen guests and pyridine ligands in these porphyrin cages are accompanied by significant conformational reorganizations of the hosts. Despite these structural changes, association constants are still very high, revealing that not only receptors that bind guests according to a lock‐and‐key mechanism but also those that bind guests by an induced‐fit mechanism can exhibit strong binding.