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Molecular Recognition of Azobenzene Dicarboxylates by Acridine‐Based Receptor Molecules; Crystal Structure of the Supramolecular Inclusion Complex of trans ‐3,3′‐Azobenzene Dicarboxylate with a Cyclo‐bis‐intercaland Receptor
Author(s) -
Cudic Predrag,
Vigneron JeanPierre,
Lehn JeanMarie,
Cesario Michèle,
Prangé Thierry
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199910)1999:10<2479::aid-ejoc2479>3.0.co;2-n
Subject(s) - azobenzene , chemistry , acridine , supramolecular chemistry , intercalation (chemistry) , molecule , crystallography , stereochemistry , crystal structure , organic chemistry
The water soluble acyclic 1 and macrocyclic 2 receptor molecules, based on acridine units, form 1:1 complexes with the cis ‐ or trans ‐2,2′ and 3,3′‐azobenzene dicarboxylate substrates. The stability constants of these complexes, determined by 1 H NMR spectroscopy, cover a wide range from 30 to 10 5 M –1 , thus displaying very pronounced structure selectivity with respect to both substitution pattern and cis , trans configuration. The complexes of the cyclo‐bis‐intercaland receptor 2 are two or three orders of magnitude more stable than those of 1 . The inclusion complex of cyclo‐bis‐intercaland 2 with trans ‐3,3′‐ azobenzene dicarboxylate has been isolated and its structure has been determined by X‐ray crystallography using synchrotron radiation, confirming the intercalation of the substrate between the acridine residues in the species formed.