Rational Functionalization of a C70 Buckybowl to Enable a C70:Buckybowl Cocrystal for Organic Semiconductor Applications

Guangpeng Gao, Meng Chen, Josiah Roberts, Meng Feng, Chengyi Xiao, Guowei Zhang, Sean Parkin, Chad Risko, Lei Zhang

Research output: Contribution to journalArticlepeer-review

49 Scopus citations


Fullerene fragments, referred to as buckybowls, are garnering interest due to their distinctive molecular shapes and optoelectronic properties. Here, we report the synthesis and characterization of a novel C70 subunit, diindeno[4,3,2,1-fghi:4′,3′,2′,1′-opqr]perylene, that is substituted with either triethylsilyl(TES)-ethynyl or 2,4,6-triisopropylphenyl groups at the meta-positions. The resulting compounds (1 and 2) display a bowl-to-bowl inversion at room temperature. Notably, the substituent groups on the meta-positions alter both the geometric and the electronic properties as well as the crystal packing of the buckybowls. In contrast to the 2,4,6-triisopropylphenyl groups in 2, the TES-ethynyl groups in 1 lead to enhanced bond length alternation, resulting in weaker aromaticity of the six-membered rings of the buckybowl skeleton. 1 forms one-dimensional (1D) concave-in-convex stacking columns, and when 1 is blended with C70, the buckybowls encapsulate C70 and result in two-dimensional cocrystals. Organic field-effect transistor (OFET) measurements demonstrate that 1 displays a hole mobility of 0.31 cm2 V-1 s-1, and the 1-C70 cocrystal exhibits ambipolar transport characteristics with electron and hole mobilities approaching 0.40 and 0.07 cm2 V-1 s-1, respectively. This work demonstrates the potential of buckybowls for the development of organic semiconductors.

Original languageEnglish
Pages (from-to)2460-2470
Number of pages11
JournalJournal of the American Chemical Society
Issue number5
StatePublished - Feb 5 2020

Bibliographical note

Publisher Copyright:
Copyright © 2020 American Chemical Society.

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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