Efficient synthesis of diethyl benzo[c]cinoline-3,8-dicarboxylate for fluorescence quenching materials†
Abstract
An intriguing reaction for direct construction of diethyl benzo[c]cinoline-3,8-dicarboxylate (2) was developed. The synthetic route was improved, the operation procedure was simplified, and the total yield was enhanced. The single crystal structure of the intermediate was obtained and a possible reaction mechanism was speculated. Moreover, compound 2 and its hydrolysis product were employed as fast and extremely efficient sensors for sensitive optical detection of picric acid (TNP) for the first time. These fluorescence quenching materials are capable of sensing TNP in real water samples, which is important in terms of practical application. In addition, we also analysed the working principle for the detection of TNP by density functional theory.