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Tuning the Electron Affinity and Stacking Properties of Corannulene by Introduction of Fluorinated Thioethers. | LitMetric

Tuning the Electron Affinity and Stacking Properties of Corannulene by Introduction of Fluorinated Thioethers.

Chem Asian J

Freie Universität Berlin, Fachbereich Biologie, Chemie, Pharmazie, Institut für Chemie und Biochemie, Fabeckstraße 34-36, 14195, Berlin, Germany.

Published: October 2018

AI Article Synopsis

Article Abstract

Trifluoromethylthio-substituted corannulene can be easily synthesized in good yield by the reaction of iodocorannulene with CuSCF . Oxidation with meta-chloroperbenzoic acid (mCPBA) yields the corresponding sulfonyl compound which exhibits the largest anodic shift of the redox potential caused by a single substituent. Similarly, four SCF , SC F and SeC F substituents are introduced in the 1,2,5,6-positions of corannulene starting with 1,2,5,6-tetraiodo- or 1,2,5,6-tetrabromocorannulene, respectively. The reactions are performed in polar aprotic solvents and are believed to follow S Ar-type substitution mechanisms. Crystal and molecular structures of selected compounds were elucidated by X-ray crystallography. Trifluoromethanesulfonyl corannulene and the fourfold-substituted trifluoromethylthioether exhibit a perfect columnar stacking of the bowls. The substituted corannulenes were investigated electrochemically by cyclic voltammetry giving raise to large anodic shifts owing to substitution with electron-withdrawing groups.

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Source
http://dx.doi.org/10.1002/asia.201801311DOI Listing

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