Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 48, Pages 21620-21626Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202007815
Keywords
ball milling; fused-ring systems; mechanochemistry; solventless reactions; sustainable chemistry
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Funding
- Ministry of Education Singapore under the AcRF Tier 1 [2019-T1-002-066, RG106/19, 2018-T1-001-176, RG18/18]
- Agency for Science, Technology and Research (A*STAR) [AME IRG A1883c0006, A1783c0003]
- NTU [04INS000171C230, M4080552]
- NIIF HPC Hungary [85708]
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It is shown that corannulene-based strained pi-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 pi-systems.
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