Synthesis and Conformational Switching of Partially and Differentially Bridged Resorcin[4]arenes Bearing Fluorescent Dye Labels. Preliminary Communication
✍ Scribed by Vladimir A. Azov; François Diederich; Yoriko Lill; Bert Hecht
- Publisher
- John Wiley and Sons
- Year
- 2003
- Tongue
- German
- Weight
- 129 KB
- Volume
- 86
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
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.