A specific nucleophilic ring-opening reaction of aziridines as a unique platform for the construction of hydrogen polysulfides sensors

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

doi:10.1021/acs.orglett.5b01194

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A specific nucleophilic ring-opening reaction of aziridines as a unique platform for the construction of hydrogen polysulfides sensors

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A specific nucleophilic ring-opening reaction of aziridines as a unique platform for the construction of hydrogen polysulfides sensors

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

Organic letters, Vol.17(11), pp.2776-2779

06/05/2015

DOI: https://doi.org/10.1021/acs.orglett.5b01194

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https://hdl.handle.net/2376/116278

PMCID: PMC4460920

PMID: 25961957

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Abstract

Hydrogen

Stereoisomerism

Sulfides - chemistry

Molecular Structure

Photons

Aziridines - chemistry

Aziridines - chemical synthesis

Photochemical Processes

A hydrogen polysulfide mediated aziridine ring-opening reaction was discovered. Based on this reaction, a novel H2S(n)-specific chemosensor (AP) was developed. AP showed high sensitivity and selectivity for H2S(n). Notably, the fluorescent turn-on product (1) exhibited excellent two-photon photophysical properties, a large Stokes shift, and high solid state luminescent efficiency.

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Title: A specific nucleophilic ring-opening reaction of aziridines as a unique platform for the construction of hydrogen polysulfides sensors
Creators: Wei Chen - †Department of Chemistry, Washington State University, Pullman, Washington 99164, United States
Ethan W Rosser - †Department of Chemistry, Washington State University, Pullman, Washington 99164, United States
Di Zhang - †Department of Chemistry, Washington State University, Pullman, Washington 99164, United States
Wen Shi - ‡Key Laboratory of Analytical Chemistry for Living Biosystems, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
Yilin Li - §Voiland School of Chemical Engineering and Bioengineering, Washington State University, Pullman, Washington 99164, United States
Wen-Ji Dong - §Voiland School of Chemical Engineering and Bioengineering, Washington State University, Pullman, Washington 99164, United States
Huimin Ma - ‡Key Laboratory of Analytical Chemistry for Living Biosystems, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
Dehong Hu - ∥William R. Wiley Environmental Molecular Science Laboratory, Pacific Northwest National Laboratory (PNNL), Richland, Washington 99352, United States
Ming Xian - †Department of Chemistry, Washington State University, Pullman, Washington 99164, United States
Publication Details: Organic letters, Vol.17(11), pp.2776-2779
Academic Unit: Chemistry, Department of; Chemical Engineering and Bioengineering, School of
Publisher: United States
Grant note: R01GM088226 / NIGMS NIH HHS R01 GM088226 / NIGMS NIH HHS R01 HL116571 / NHLBI NIH HHS R01HL116571 / NHLBI NIH HHS
Identifiers: 99900547340801842
Language: English
Resource Type: Journal article