文献类型：期刊文献

英文题名：Photophysics of perylene monoimide-labelled organocatalysts

作者：Zheng, Dongdong[1];Oskouei, Mina Raeisolsadati[1];Sanders, Hans J.[1];Qian, Junhong[1,2];Williams, Rene M.[1];Brouwer, Albert M.[1]

机构：[1]Univ Amsterdam, vant Hoff Inst Mol Sci, POB 94157, NL-1090 GD Amsterdam, Netherlands;[2]East China Univ Sci & Technol, 130 Meilong Rd, Shanghai 200237, Peoples R China

年份：2019

卷号：18

期号：2

起止页码：524

外文期刊名：PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000458569100025)】；

基金：We thank the China Scholarship Council for a scholarship (no. 201406170063) to Dongdong Zheng. Fengshou Yu is gratefully acknowledged for the electrochemistry measurement. Steven Kettelarij performed the synthesis of PMI-dHQD 2. Michiel Hilbers helped with the spectroscopy experiments.

语种：英文

摘要：We designed and synthesized cinchona alkaloid derivates PMI-BnCPD, 1 and PMI-dHQD, 2, in which a fluorescent perylene monoimide unit is linked to the quinuclidine fragment. The latter acts as an electron donor, quenching the perylene imide fluorescence in polar solvents. In the organocatalytic application of these compounds, the electron donor is deactivated by binding to an electrophile, e.g. H+. We show that this restores the fluorescence, allowing the compounds to signal the electrophile binding step that occurs in many catalytic reactions. In order to demonstrate that charge transfer is indeed the fluorescence quenching mechanism, we detected the charge separated state by means of transient absorption spectroscopy. Incidentally, the excited state absorption bands of the locally excited and charge transfer states are very similar. The activity of the fluorophore labeled organocatalyst 1 in a fluorogenic Michael addition reaction is demonstrated.