A Specific Nucleophilic Ring-Opening Reaction of Aziridines as a Unique Platform for the Construction of Hydrogen Polysulfides Sensors
- Washington State Univ., Pullman, WA (United States). Dept. of Chemistry
- Chinese Academy of Sciences (CAS), Beijing (China). Inst. of Chemistry, Key Lab. of Analytical Chemistry for Living Biosystems
- Washington State Univ., Pullman, WA (United States). Voiland School of Chemical Engineering and Bioengineering
- Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
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.
- Research Organization:
- Pacific Northwest National Laboratory (PNNL), Richland, WA (United States). Environmental Molecular Sciences Laboratory (EMSL)
- Sponsoring Organization:
- USDOE Office of Science (SC), Biological and Environmental Research (BER); National Institutes of Health (NIH)
- Grant/Contract Number:
- AC05-76RL01830; R01GM088226; R01HL116571
- OSTI ID:
- 1208715
- Report Number(s):
- PNNL-SA-108754; 48706; KP1704020
- Journal Information:
- Organic Letters, Vol. 17, Issue 11; ISSN 1523-7060
- Publisher:
- American Chemical SocietyCopyright Statement
- Country of Publication:
- United States
- Language:
- English
Web of Science
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