Fluoride-Induced Formation of Triphenylene Chemodosimeter

Significance

During the TBS deprotection of a highly oxygenated terphenylene derivative with tetrabutylammonium fluoride (TBAF) the authors noted an unusual and near-quantitative cyclization to the triphenylene. Subsequent mechanistic investigations have shown the necessity of at least four phenolate anions for the oxidative cyclization/dehydrogenation to occur. The authors also utilized the increased color change that occurs upon formation of the triphenylene as a potential fluoride chemodosimeter. The sensor was specific for fluoride over a variety of anions, was shown to have a submillimolar detection range, and is detectable visually.