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Synthesis and Conformational Switching of Partially and Differentially Bridged Resorcin[4]arenes Bearing Fluorescent Dye Labels. Preliminary Communication
Author(s) -
Azov Vladimir A.,
Diederich François,
Lill Yoriko,
Hecht Bert
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390172
Subject(s) - chemistry , fluorescence , molecule , stereochemistry , proton nmr , organic chemistry , physics , quantum mechanics
We report the synthesis of modified Cram ‐type cavitands bearing one or two fluorescent labels for single‐molecule spectroscopic studies of vasekite conformational switching ( Scheme 3 ). Syntheses were performed by stepwise bridging of the four couples of neighboring H‐bonded OH groups of resorcin[4]arene bowls ( Schemes 2 and 3 ). The new substitution patterns enable the construction of a large variety of future functional architectures. 1 H‐NMR Investigations showed that the new partially and differentially bridged cavitands feature temperature‐ and pH‐triggered vasekite conformational isomerism similar to symmetrical cavitands with four identical quinoxaline bridges ( Table ). It was discovered that vasekite switching of cavitands is strongly solvent‐dependent.