Staff Publications

Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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Record number 539520
Title Quantitative and Orthogonal Formation and Reactivity of SuFEx Platforms
Author(s) Gahtory, Digvijay; Sen, Rickdeb; Pujari, Sidharam; Li, Suhua; Zheng, Qinheng; Moses, John E.; Sharpless, K.B.; Zuilhof, Han
Source Chemistry-A European Journal 24 (2018)41. - ISSN 0947-6539 - p. 10550 - 10556.
DOI https://doi.org/10.1002/chem.201802356
Department(s) Laboratory for Organic Chemistry
VLAG
Publication type Refereed Article in a scientific journal
Publication year 2018
Keyword(s) click chemistry - fluorine - sulfur - surface chemistry - surface modification
Abstract

The constraints of minute reactant amounts and the impossibility to remove any undesired surface-bound products during monolayer functionalization of a surface necessitate the selection of efficient, modular and orthogonal reactions that lead to quantitative conversions. Herein, we explore the character of sulfur–fluoride exchange (SuFEx) reactions on a surface, and explore the applicability for quantitative and orthogonal surface functionalization. To this end, we demonstrate the use of ethenesulfonyl fluoride (ESF) as an efficient SuFEx linker for creating “SuFEx-able” monolayer surfaces, enabling three distinct approaches to utilize SuFEx chemistry on a surface. The first approach relies on a di-SuFEx loading allowing dual functionalization with a nucleophile, while the two latter approaches focus on dual (CuAAC–SuFEx/SPOCQ–SuFEx) click platforms. The resultant strategies allow facile attachment of two different substrates sequentially on the same platform. Along the way we also demonstrate the Michael addition of ethenesulfonyl fluoride to be a quantitative surface-bound reaction, indicating significant promise in materials science for this reaction.

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