A Short Review on Recent Advances and Applications of Bimane Chemistry

Abstract

1,5-diazabicyclo[3.3.0]octadienediones, also known as bimanes, are heterobicyclic compounds with generally high quantum yields, low toxicity, and low molecular weight. During the 1970s, the bimane fluorophore, which was synthesized from the reaction of a beta-keto ester and hydrazine, was first reported by Kosower and co-workers. Since that time, significant effort has been invested in the introduction of functional groups at the alpha-positions of syn-bimane, the bimane isomer in which both carbonyl groups are oriented in the same direction. In spite of these efforts, the successful attachment of high value functional groups at the alpha-positions of syn-bimane remain scarce. A recent report from Prof. Flavio Grynszpan's group using a solvent-free, environmentally friendly (i.e. "green") method allowed for a rapid, large-scale synthesis of bimane and the preparation and study of differently-substituted bimane derivatives. In this review, we describe the advantages of the current green synthesis of bimanes and the applications of the newly formed bimane derivatives as fluorescent and colorimetric sensors, with special attention paid to the relationship between the bimane structures, their photophysical characteristics, and their performance as chemical sensors.