Triboluminescence is the property of a class of compounds that spontaneously emit light upon mechanical fracture. Compounds that exhibit triboluminescence can be used in applications including pressure sensors. The optical and structural features required for triboluminescence to occur are poorly understood. Evidence suggests that noncentrosymmetric packing is a requirement for compounds to exhibit triboluminescence. Salts involving chiral cations paired with photoluminescent metal complexes were chosen as potential triboluminescent synthetic targets. As single enantiomer compounds are either expensive or difficult to obtain, we looked to employ cinchonine, a readily available and inexpensive single enantiomer natural product obtained from cinchona trees. An N-benzyl derivative of cinchonine (N-Bzcinch)Br (N-Bzcinch = N-benzylcinchonidinium), was synthesized and characterized by 1H NMR, solid-state photoluminescence, and X-ray structures. Two X-ray structures were obtained of N-benzylcinchonidinium bromide, an anhydrous form and a 1.5 hydrate. Both single enantiomer structures crystallize in chiral space groups, but exhibit different packing in large part due to hydrogen-bonding. Both salts also exhibit green solid-state photoluminescence. As several salts of [MnBr4]2- exhibit triboluminescence, our next goal is to synthesize salts of the form (N-Bzcinch)2[MnBr4].

Structural studies of N-benzylcinchonidinium bromide for use in triboluminescent complexes

2019 Spring National Meeting

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.