Modulation of ICT and PET processes in boranil derivatives: a ratiometric fluorescent probe for imaging of cysteine

Abstract

1 is the first ratiometric fluorescent probe for imaging of intracellular Cys based on boranil derivatives modulated by ICT and PET processes with fast response, high sensitivity, excellent selectivity.

Cooperation of ESIPT and ICT Processes in the Designed 2-(2′-Hydroxyphenyl)benzothiazole Derivative: A Near-Infrared Two-Photon Fluorescent Probe with a Large Stokes Shift for the Detection of Cysteine and Its Application in Biological Environments

“…The mechanism by which the acrylates work as the responsive groups to Cys is as follows: Michael addition of Cys to the acrylates to yield the thioether intermediates, which are intramolecularly cyclized to give lactams and to release free fluorophores. ,,− To further rationalize the sensing mechanism of SDP-A toward Cys, we carried out the related product analysis by HRMS (ESI) and 1 H NMR. Upon addition of significant excess of Cys, the molecular ion peak ([M] + ) of the probe SDP-A , found as 425.1317 ( m / z ) (Figure S7A), almost disappeared along with appearance of two new signal peaks, corresponding to the free fluorophore SDP at 371.1212 ( m / z ) and the thioether intermediate at 546.1513 ( m / z ) (Figure S7B).…”

A novel fluorescent probe with a large Stokes shift for colorimetric and selective detection of cysteine in water, milk, cucumber, pear and tomato

“…When Cys was added, the Michael addition occurred between Cys and probe 2, and then generated seven-membered cyclolactam and uorophore compound 4 (Scheme 2a) through the intramolecular cyclization. 28,[37][38][39][40][41] Moreover, due to the inuence of ring tension and spatial steric hindrance, 26 probe 2 had a poor ability to identify Hcy and GSH. Furthermore, the reaction between probe 2 and Cys was further supported by in situ 1 H NMR study (Scheme 2b).…”

Donor–Acceptor Boron-Ketoiminate Complexes with Pendent N-Heterocyclic Arms: Switched-on Luminescence through N-Heterocycle Methylation

“…In this context, Gardinier and co-workers have investigated the impact on the electronic structure of difluoroboron complexes upon mono- and disubstitution of the oxygen-donor atoms with nitrogen, revealing the intermediacy of the difluoroboron β-ketominates as electron donors and acceptors compared to symmetric O^O or N^N chelates . Of the various N^O-containing difluoroboron complexes that have been reported, ,− considerable attention has been dedicated to the boranil analogues ( D ), first reported by Ziessel and co-workers, from both application − and theoretical points of view.…”