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FRET Studies on a Series of BODIPY‐Dye‐Labeled Switchable Resorcin[4]arene Cavitands
Author(s) -
Pochorovski Igor,
Breiten Benjamin,
Schweizer W. Bernd,
Diederich François
Publication year - 2010
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.201001625
Subject(s) - bodipy , förster resonance energy transfer , chemistry , fluorescence , cavitand , fluorescence spectroscopy , spectroscopy , nuclear magnetic resonance spectroscopy , photochemistry , two dimensional nuclear magnetic resonance spectroscopy , supramolecular chemistry , molecule , stereochemistry , organic chemistry , physics , quantum mechanics
A series of borondipyrromethane (BODIPY)‐dye‐labeled resorcin[4]arene cavitands 1 – 4 with different lengths of oligo(phenylene–ethynylene) spacers between the dyes and the macrocyclic rim has been synthesized. Their switching behavior from the “vase” to “kite” conformations in bulk solution was examined by both variable‐temperature (VT) NMR and fluorescence spectroscopy. Both VT‐NMR and VT fluorescence resonance energy transfer (FRET) experiments showed that cavitands 1 – 4 undergo vase‐to‐kite switching at low temperatures. Acid‐triggered switching to the kite conformation was observed by fluorescence spectroscopy. Quantitative evaluation of the FRET data led to the determination of the Förster radius R 0 =37 Å for the BODIPY‐dye FRET pair and an average cavitand opening angle α =16° in the vase conformation.