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

Abstract

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
Volume142
Issue number5
DOIs
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

Fingerprint

Dive into the research topics of 'Rational Functionalization of a C70 Buckybowl to Enable a C70:Buckybowl Cocrystal for Organic Semiconductor Applications'. Together they form a unique fingerprint.

Cite this