Spontaneous Assembly and Three‐Dimensional Stacking of Antiaromatic 5,15‐Dioxaporphyrin on HOPG

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  • Chen, Tsang‐Wei Matt
    Department of Chemistry and Center for Emerging Material and Advanced Devices National Taiwan University
  • Tanaka, Yuki
    Department of Applied Chemistry Graduate School of Engineering, Kyushu University Center for Molecular Systems (CMS) Kyushu University
  • Kametani, Yohei
    Institute for Materials Chemistry and Engineering and Integrated Research Consortium on Chemical Science Kyushu University
  • Cheng, Kum‐Yi
    Department of Chemistry and Center for Emerging Material and Advanced Devices National Taiwan University
  • Lin, Chih‐Hsun
    Department of Chemistry and Center for Emerging Material and Advanced Devices National Taiwan University
  • Lin, Yi Rick
    Department of Chemistry and Center for Emerging Material and Advanced Devices National Taiwan University
  • Hsu, Ting‐Rong
    Department of Chemistry and Center for Emerging Material and Advanced Devices National Taiwan University
  • Chen, Zuqian
    Department of Applied Chemistry Graduate School of Engineering, Kyushu University Center for Molecular Systems (CMS) Kyushu University
  • Hao, Jiping
    Department of Applied Chemistry Graduate School of Engineering, Kyushu University Center for Molecular Systems (CMS) Kyushu University
  • Mori, Shigeki
    Advanced Research Center (ADRES) Ehime University
  • Shiota, Yoshihito
    Institute for Materials Chemistry and Engineering and Integrated Research Consortium on Chemical Science Kyushu University
  • Yoshizawa, Kazunari
    Institute for Materials Chemistry and Engineering and Integrated Research Consortium on Chemical Science Kyushu University
  • Furuta, Hiroyuki
    Department of Applied Chemistry Graduate School of Engineering, Kyushu University Center for Molecular Systems (CMS) Kyushu University
  • Shimizu, Soji
    Department of Applied Chemistry Graduate School of Engineering, Kyushu University Center for Molecular Systems (CMS) Kyushu University
  • Chen, Chun‐hsien
    Department of Chemistry and Center for Emerging Material and Advanced Devices National Taiwan University

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Antiaromatic compounds have recently received considerable attention because of their novel properties such as narrow HOMO–LUMO gaps and facile formation of mutual stacking. Here, the spontaneous assembly of antiaromatic meso-2-thienyl-substituted 5,15-dioxaporphyrin (DOP-1) is scrutinized at the liquid-solid interface by scanning tunneling microscopy (STM). Polymorphism in monolayers characterized by the orthogonal and parallel assemblies is found at the low concentration of 0.05 mM. The parallel assembly is more stable and dominantly formed at higher concentrations. Aggregation was observed at concentrations >0.2 mM, and the STM images of the aggregates implied the formation of stacked layers. The intrinsic electronic structures of the mutually stacked bilayer generated by applying an electric pulse to the monolayer were probed by scanning tunneling spectroscopy to reveal the narrowing of the HOMO–LUMO gap by about 20 % compared with the monolayer, thus suggesting significant molecular orbital interactions.

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