Big, strong, neutral, twisted, and chiral π acids

Chemistry : a European Journal
Yingjie ZhaoStefan Matile

Abstract

General synthetic access to expanded π-acidic surfaces of variable size, topology, chirality, and π acidity is reported. The availability of π surfaces with these characteristics is essential to develop the functional relevance of anion-π interactions with regard to molecular recognition, translocation, and transformation. The problem is that, with expanded π surfaces, the impact of electron-withdrawing substituents decreases and the high π acidity needed for strong anion-π interactions can be more difficult to obtain. To overcome this problem, it is herein proposed to build large surfaces from smaller fragments and connect these fragments with bridges that are composed only of single atoms. Two central surfaces for powerful anion-π interactions, namely, perfluoroarenes and naphthalenediimides (NDIs), were selected as fragments and coupled with through sulfide bridges. Their oxidation to sulfoxides and sulfones, as well as fluorine substitution in the peripheral rings, provides access to the full chemical space of relevant π acidities. According to cyclic voltammetry, LUMO levels range from -3.96 to -4.72 eV. With sulfoxide bridges, stereogenic centers are introduced to further enrich the intrinsic planar chirality of the expan...Continue Reading

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Citations

Sep 9, 2015·Journal of the American Chemical Society·Yingjie ZhaoStefan Matile
Aug 27, 2016·Chemical Reviews·Mohammad Al KobaisiSheshanath V Bhosale
Aug 11, 2017·Chemistry : a European Journal·Chao Wang, Stefan Matile
Dec 15, 2015·Chemistry : a European Journal·François N MirosStefan Matile
Feb 20, 2020·Chemical Communications : Chem Comm·Zhaohui ZhangYingjie Zhao
Dec 14, 2018·Journal of the American Chemical Society·Xiang ZhangStefan Matile

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