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Mechanochemical Synthesis of Corannulene‐Based Curved Nanographenes
Author(s) -
Báti Gábor,
Csókás Dániel,
Yong Teoh,
Tam Si Man,
Shi Raymond R. S.,
Webster Richard D.,
Pápai Imre,
García Felipe,
Stuparu Mihaiela C.
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202007815
Subject(s) - corannulene , cyclic voltammetry , mechanochemistry , chemistry , spectroscopy , materials science , chemical physics , nanotechnology , electrochemistry , computational chemistry , molecule , organic chemistry , electrode , physics , quantum mechanics
It is shown that corannulene‐based strained π‐surfaces can be obtained through the use of mechanochemical Suzuki and Scholl reactions. Besides being solvent‐free, the mechanochemical synthesis is high‐yielding, fast, and scalable. Therefore, gram‐scale preparation can be carried out in a facile and sustainable manner. The synthesized nanographene structure carries positive (bowl‐like) and negative (saddle‐like) Gaussian curvatures and adopts an overall quasi‐monkey saddle‐type of geometry. In terms of properties, the non‐planar surface exhibits a high electron affinity that was measured by cyclic voltammetry, with electrolysis and in situ UV/vis spectroscopy experiments indicating that the one‐electron reduced state displays a long lifetime in solution. Overall, these results indicate the future potential of mechanochemistry in accessing synthetically challenging and functional curved π‐systems.