A Specific Nucleophilic Ring-Opening Reaction of Aziridines as a Unique Platform for the Construction of Hydrogen Polysulfides Sensors
Abstract
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.
- Authors:
-
- 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)
- Publication Date:
- Research Org.:
- Pacific Northwest National Laboratory (PNNL), Richland, WA (United States). Environmental Molecular Sciences Laboratory (EMSL)
- Sponsoring Org.:
- USDOE Office of Science (SC), Biological and Environmental Research (BER); National Institutes of Health (NIH)
- OSTI Identifier:
- 1208715
- Report Number(s):
- PNNL-SA-108754
Journal ID: ISSN 1523-7060; 48706; KP1704020
- Grant/Contract Number:
- AC05-76RL01830; R01GM088226; R01HL116571
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Organic Letters
- Additional Journal Information:
- Journal Volume: 17; Journal Issue: 11; Journal ID: ISSN 1523-7060
- Publisher:
- American Chemical Society
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Nucleophilic; aziridines; fluorescence; hydrogen; polysulfides; Environmental Molecular Sciences Laboratory
Citation Formats
Chen, Wei, Rosser, Ethan W., Zhang, Di, Shi, Wen, Li, Yilin, Dong, Wen-Ji, Ma, Huimin, Hu, Dehong, and Xian, Ming. A Specific Nucleophilic Ring-Opening Reaction of Aziridines as a Unique Platform for the Construction of Hydrogen Polysulfides Sensors. United States: N. p., 2015.
Web. doi:10.1021/acs.orglett.5b01194.
Chen, Wei, Rosser, Ethan W., Zhang, Di, Shi, Wen, Li, Yilin, Dong, Wen-Ji, Ma, Huimin, Hu, Dehong, & Xian, Ming. A Specific Nucleophilic Ring-Opening Reaction of Aziridines as a Unique Platform for the Construction of Hydrogen Polysulfides Sensors. United States. https://doi.org/10.1021/acs.orglett.5b01194
Chen, Wei, Rosser, Ethan W., Zhang, Di, Shi, Wen, Li, Yilin, Dong, Wen-Ji, Ma, Huimin, Hu, Dehong, and Xian, Ming. Mon .
"A Specific Nucleophilic Ring-Opening Reaction of Aziridines as a Unique Platform for the Construction of Hydrogen Polysulfides Sensors". United States. https://doi.org/10.1021/acs.orglett.5b01194. https://www.osti.gov/servlets/purl/1208715.
@article{osti_1208715,
title = {A Specific Nucleophilic Ring-Opening Reaction of Aziridines as a Unique Platform for the Construction of Hydrogen Polysulfides Sensors},
author = {Chen, Wei and Rosser, Ethan W. and Zhang, Di and Shi, Wen and Li, Yilin and Dong, Wen-Ji and Ma, Huimin and Hu, Dehong and Xian, Ming},
abstractNote = {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.},
doi = {10.1021/acs.orglett.5b01194},
journal = {Organic Letters},
number = 11,
volume = 17,
place = {United States},
year = {Mon May 11 00:00:00 EDT 2015},
month = {Mon May 11 00:00:00 EDT 2015}
}
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