超分子ボロン錯体の合成と分子認識
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概要
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Tandem Claisen rearrangement enabled us to produce noncyclic and macrocyclic catechol ligands with plural phenolic hydroxy groups from the corresponding di-isobutenyl polyether derivatives having various functional groups such as ester, amide, and aromatic rings. Complexation of the resultant catechol ligands with boronic acid selectively and effectively gave supramolecular boron complexes, in which only the catechol moiety reacted with boronic acid. The free phenolic hydroxy and ester groups assembled in the boron complex B1 was able to act as metal binding site, while the amide groups, quinoline, and oxyethylene moieties in the boron complex B2-B5 form multiple hydrogen bond formation with anions such as halogen, phosphate, acetate, and sulfate ions. The selectivity and the binding strength on the molecular recognition strongly depend on the variation and stereospecificity of the functional groups in the boron complexes, in addition to the coordination structure and charge of the boron in the boron complexes. Thus, introduction of chromophoric or fluorophoric group into the boron complexes allowed us to construct optical sensing systems for target molecules.
- 社団法人 有機合成化学協会の論文
- 2007-10-01
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