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Title: A Specific Nucleophilic Ring-Opening Reaction of Aziridines as a Unique Platform for the Construction of Hydrogen Polysulfides Sensors

Hydrogen polysulfides (H 2S n, n>1) have been recently suggested to be the actual signalling molecules that involved in sulfur-related redox biology. However the exact mechanisms of H 2S n are still poorly understood and a major hurdle in this field is the lack of reliable and convenient methods for H 2S n detection. In this work we report a unique ring-opening reaction of N-sulfonylaziridine by Na 2S 2 under mild conditions. Based on this reaction a novel H 2S n-specific fluorescent probe (AP) was developed. The probe showed high sensitivity and selectivity for H 2S n. 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.
 [1] ;  [1] ;  [1] ;  [2] ;  [3] ;  [3] ;  [2] ;  [4] ;  [1]
  1. Washington State Univ., Pullman, WA (United States). Dept. of Chemistry
  2. Chinese Academy of Sciences (CAS), Beijing (China). Inst. of Chemistry, Key Lab. of Analytical Chemistry for Living Biosystems
  3. Washington State Univ., Pullman, WA (United States). Voiland School of Chemical Engineering and Bioengineering
  4. Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
Publication Date:
OSTI Identifier:
Report Number(s):
Journal ID: ISSN 1523-7060; 48706; KP1704020
Grant/Contract Number:
AC05-76RL01830; R01GM088226; R01HL116571
Accepted Manuscript
Journal Name:
Organic Letters
Additional Journal Information:
Journal Volume: 17; Journal Issue: 11; Journal ID: ISSN 1523-7060
American Chemical Society
Research Org:
Pacific Northwest National Lab. (PNNL), Richland, WA (United States). Environmental Molecular Sciences Lab. (EMSL)
Sponsoring Org:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23); National Institutes of Health (NIH)
Country of Publication:
United States
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Nucleophilic; aziridines; fluorescence; hydrogen; polysulfides; Environmental Molecular Sciences Laboratory