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Angew Chem Int Ed Engl. 2019 Apr 1;58(15):5044-5048. doi: 10.1002/anie.201901274. Epub 2019 Mar 6.

Converting Thioether Waste into Organic Semiconductors by Carbon-Sulfur Bond Activation.

Author information

1
Center of Materials Science and Optoelectronics Engineering, College of Materials Science and Opto-Electronic Technology & CAS Center for Excellence in Topological Quantum Computation & CAS Key Laboratory of Vacuum Physic, University of Chinese Academy of Sciences, Beijing, 100049, P. R. China.
2
Key Laboratory of Organic Solids, Beijing National Laboratory for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, P. R. China.
3
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China.
4
School of Materials Science and Engineering, South China University of Technology, Guangzhou, 510640, China.

Abstract

A goal for human society is to convert organic waste into valuable materials. Herein, 2-(methylthio)-bezothiazole (MTBT), an important organic waste in urban runoff, was catalytically converted into a series of organic semiconductors through carbon-sulfur bond activation. The efficient conversion of various substrates with different aromatic moieties and reacting functional groups (tin and boron) proved the generality of this novel diarylation Liebeskind-Srogl methodology. Moreover, the resulting organic semiconductors showed excellent performance in field effect transistors and cell imaging. This contribution presents an excellent example of converting organic waste into valuable materials and may open a new avenue to utilizing widely available aromatic thioethers.

KEYWORDS:

cross-coupling; homogenous catalysis; organic waste; semiconductors; sulfur

PMID:
30793823
DOI:
10.1002/anie.201901274

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