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Threading a Linear Molecule Through a Macrocycle Thanks to Boron: Optical Properties of the Threaded Species and
Matthieu Hicguet1, Ludmilla Verrieux1, Olivier Mongin1
1Univ Rennes, École Nationale Supérieure de Chimie de Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) - UMR6226, F-35000, Rennes, France.
Abstract:
Two BODIPYs and two boron β-diketonates were threaded through a macrocycle bearing a 2,2'-biphenol unit, showing thus the ability of boron to act as a gathering atom. The new threaded species were characterized by 1D and 2D NMR spectroscopy as well as by X-ray crystallography for one of them and their properties rationalized with quantum chemistry to unravel the vibronic contributions. The BODIPYs exhibited interesting fluorescence features with quantum yields up to 91 % and enhanced photostability compared to their non-threaded homologues. A rotaxane was synthesized using this threading strategy after stoppering and removing the boron with potassium hydroxide.
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