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

Tsang Wei Matt Chen, Yuki Tanaka, Yohei Kametani, Kum Yi Cheng, Chih Hsun Lin, Yi Rick Lin, Ting Rong Hsu, Zuqian Chen, Jiping Hao, Shigeki Mori, Yoshihito Shiota, Kazunari Yoshizawa, Hiroyuki Furuta, Soji Shimizu, Chun hsien Chen

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8 Citations (Scopus)


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.

Original languageEnglish
Article numbere202212726
JournalAngewandte Chemie - International Edition
Issue number48
Publication statusPublished - Nov 25 2022

All Science Journal Classification (ASJC) codes

  • Catalysis
  • General Chemistry


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