Mechanochemical Synthesis of Corannulene-Based Curved Nanographenes.

Autor: Báti G; Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University Singapore, 21 Nanyang Link, 637371, Singapore, Singapore., Csókás D; Institute of Organic Chemistry, Research Centre for Natural Sciences, Magyar tudósok körútja 2, 1117, Budapest, Hungary., Yong T; Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University Singapore, 21 Nanyang Link, 637371, Singapore, Singapore., Tam SM; Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University Singapore, 21 Nanyang Link, 637371, Singapore, Singapore., Shi RRS; Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University Singapore, 21 Nanyang Link, 637371, Singapore, Singapore., Webster RD; Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University Singapore, 21 Nanyang Link, 637371, Singapore, Singapore., Pápai I; Institute of Organic Chemistry, Research Centre for Natural Sciences, Magyar tudósok körútja 2, 1117, Budapest, Hungary., García F; Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University Singapore, 21 Nanyang Link, 637371, Singapore, Singapore., Stuparu MC; Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University Singapore, 21 Nanyang Link, 637371, Singapore, Singapore.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2020 Nov 23; Vol. 59 (48), pp. 21620-21626. Date of Electronic Publication: 2020 Sep 17.
DOI: 10.1002/anie.202007815
Abstrakt: 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.
(© 2020 Wiley-VCH GmbH.)
Databáze: MEDLINE
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