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

Chen, Wei; Rosser, Ethan W.; Zhang, Di; Shi, Wen; Li, Yilin; Dong, Wen-Ji; Ma, Huimin; Hu, Dehong; Xian, Ming

doi:10.1021/acs.orglett.5b01194

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

Journal Article · Mon May 11 00:00:00 EDT 2015 · Organic Letters

DOI:https://doi.org/10.1021/acs.orglett.5b01194· OSTI ID:1208715

Chen, Wei ^[1]; Rosser, Ethan W. ^[1]; Zhang, Di ^[1]; Shi, Wen ^[2]; Li, Yilin ^[3]; Dong, Wen-Ji ^[3]; Ma, Huimin ^[2]; Hu, Dehong ^[4]; Xian, Ming ^[1]

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 (H₂S_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 H₂S_n are still poorly understood and a major hurdle in this field is the lack of reliable and convenient methods for H₂S_n 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 H₂S_n-specific fluorescent probe (AP) was developed. The probe showed high sensitivity and selectivity for H₂S_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.

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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

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Cited by: 74 works

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Nucleophilic
aziridines
fluorescence
hydrogen
polysulfides
Environmental Molecular Sciences Laboratory

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

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