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

Abstract

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.

Authors:
 [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:
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)
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. doi: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. doi: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 = {2015},
month = {5}
}

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