Oxidative cyclo-rearrangement of helicenes into chiral nanographenes

We develop a facile strategy to recompose helicenes into chiral nanographenes through a unique oxidative cyclo-rearrangement reaction

Chengshuo Shen; Guoli Zhang; Yongle Ding; Na Yang; Fuwei Gan; Jeanne Crassous; Huibin Qiu

2021

Scholarcy highlights

  • Nanographenes are emerging as a distinctive class of functional materials for electronic and optical devices
  • F ollowing the impressive development of graphene materials1,2, nanographenes with size limited in the nanometer scale are currently emerging as prominent semiconducting substances due to their open bandgap3, which is highly useful for electronic devices4, energy storage5, and sensors6
  • We explored the oxidative reactions of primitive carbohelicene 6H in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and various acids
  • X-ray diffraction of a single crystal further confirmed the formation of an unsymmetric chiral π-conjugated system in which a benzoperylene moiety was fused with a helicene skeleton
  • To gain more insights into this interesting oxidation reaction, we introduced a variety of substituents on the helicene skeleton and prepared 4-bromo, 4-fluoro, 4-trifluoromethyl, 4-methyl and 5,6-diphenyl substituted carbo helicenes, namely, 8HBr, 8HF, 8HCF3, 8HCH3, and 8H2py
  • We have developed a distinctive oxidative cyclorearrangement method to recompose the skeleton of helicenes to precisely fabricate chiral nanographenes with unique topologies and absolute configurations integrally inherited from their helical precursors

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