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
  • 田中, 裕己
    九州大学大学院工学府応用化学専攻 九州大学分子システム科学センター
  • 亀谷, 陽平
    九州大学先導物質化学研究所総合物質制化学研究推進機構
  • 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
  • 陳, 祖前
    九州大学大学院工学府応用化学専攻 九州大学分子システム科学センター
  • ハオ, ジピン
    九州大学大学院工学府応用化学専攻 九州大学分子システム科学センター
  • 森, 重樹
    愛媛大学
  • 塩田, 淑仁
    九州大学先導物質化学研究所総合物質制化学研究推進機構
  • 吉澤, 一成
    九州大学先導物質化学研究所総合物質制化学研究推進機構
  • 古田, 弘幸
    九州大学大学院工学研究院応用化学部門 九州大学分子システム科学センター
  • 清水, 宗治
    九州大学大学院工学研究院応用化学部門 九州大学分子システム科学センター
  • Chen, Chun‐hsien
    Department of Chemistry and Center for Emerging Material and Advanced Devices National Taiwan University

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説明

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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