N-type organic semiconductors based on π-deficient pentacenequinones: Synthesis, electronic structures, molecular packing, and thin film transistors

Zhixiong Liang, Qin Tang, Jing Liu, Jinhua Li, Feng Yan, Qian Miao

Research output: Journal article publicationJournal articleAcademic researchpeer-review

89 Citations (Scopus)


Quinones are well-known as organic oxidizing reagents in organic synthesis and biological systems, but their ability of accepting electrons was rarely explored in connection with n-type organic semiconductors. Here, we report a comprehensive study on two groups of π-deficient pentacenequinones, fluorinated pentacenequinones and N-heteropentacenequinones, highlighting their electronic structures,molecular packing, and n-channel thin film transistors. It is found that replacingH atoms of pentacenequinone with F atoms or replacing C atoms with N can lower the lowest unoccupied molecular orbital (LUMO) energy level of pentacenequinone to yield n-type organic semiconductors with the field effect mobility up to higher than 0.1 cm2V-1s-1 in thin film transistors. A comparison between the two groups of quinones in terms of their electronic structures and molecular packing has led to interesting findings on the roles of electron-withdrawing moieties in tuning frontier molecular orbitals and p-stacking. Another interesting finding on the molecular packing is the quadruple weak hydrogen bonds, which link the neighboring p-stacks of quinones. This study suggests that π-deficient quinones would be a general design for n-type organic semiconductors.
Original languageEnglish
Pages (from-to)6438-6443
Number of pages6
JournalChemistry of Materials
Issue number23
Publication statusPublished - 14 Dec 2010

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Materials Chemistry

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