A series of stable, six membered, boronate esters (C6F5-, C6H3F3-, C6H3Cl2-, C6H6-, Mesityl-) of different Lewis acidities was synthesized by esterification of the corresponding boronic acids with 1,8-naphtalenediol. The adduct formation of these naphthalene boronate esters with 4,4′-bipyridine has been investigated. Highly Lewis acidic boronate esters tend to form stable double tweezer shaped adducts, while the adducts derived from less Lewis acidic boronate esters tend to dissociate into their individual components. The inclusions properties of the C6H3F3- adduct double tweezer structure with a series of aromatic guest molecules such as benzene, toluene, o-xylene, m-xylene, p-xylene, mesitylene will be presented.

1,8-Naphthalenediol derived boronic esters and inclusion properties of the 4,4′-bipyridine based Lewis acid–base complexes with different aromatic guest molecules

2019 Fall National Meeting

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