Mechanochemical synthesis of corannulene-based curved nanographenes

• Main Authors: Báti, Gábor, Csókás, Dániel, Yong, Teoh, Tam, Si Man, Shi, Raymond Rong Sheng, Webster, Richard David, Pápai, Imre, García, Felipe, Stuparu, Mihaiela Corina
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2023
• Subjects: Science::Chemistry; Ball Milling; Used-Ring Systems
• Online Access: https://hdl.handle.net/10356/172345
• Institution: Nanyang Technological University

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.