Hydrogen polysulfides (H2Sn, n>1) have been recently suggested to be the actual signalling molecules that involved in sulfur-related redox biology. However the exact mechanisms of H2Sn are still poorly understood and a major hurdle in this field is the lack of reliable and convenient methods for H2Sn detection. In this work we report a unique ring-opening reaction of N-sulfonylaziridine by Na2S2 under mild conditions. Based on this reaction a novel H2Sn-specific fluorescent probe (AP) was developed. The probe showed high sensitivity and selectivity for H2Sn. Notably, the fluorescent turn-on product, i.e. compound 1, exhibited excellent two-photon photophysical properties and a large Stokes shift. Moreover, the high solid state luminescent efficiency of compound 1 makes it a potential candidate for organic emitters and solid-state lighting devices.
Revised: February 10, 2016 |
Published: May 11, 2015
Citation
Chen W., E.W. Rosser, D. Zhang, W. Shi, Y. Li, W. Dong, and H. Ma, et al. 2015.A Specific Nucleophilic Ring-Opening Reaction of Aziridines as a Unique Platform for the Construction of Hydrogen Polysulfides Sensors.Organic Letters 17, no. 11:2776-2779.PNNL-SA-108754.doi:10.1021/acs.orglett.5b01194