Yoshihiro Miyake

Graduate School of Engineering, Nagoya University
Associate Professor

Research AreasOrganic Chemistry, Coordination Chemistry
Participating Group (2020-2021)

Development of Emissive Soft Crystals through Control of Dynamic Motion of Negatively Curved π-Frameworks

Vapochromism, Thermochromism, Circulene, Negatively Curved π-Frameworks, Soft Crystal

Research Outline

Curved polycyclic aromatic hydrocarbons (PAHs) have attracted considerable attention, especially as novel π-conjugated materials. Recently we have found tetrathia[8]circulene octaoxides exhibit negatively curved annulated π-frameworks and a dynamic inversion of their saddle-shaped conformation. Especially, we have also found that tetrathia[8]circulene octaoxides 1 having peripheral aryl groups exhibited vapo- and thermochromic behaviors, through crystal-to-crystal transition. X-Ray analysis clearly suggest that this phenomenon originates from the dynamic motion of their negatively curved π-frameworks from saddle-conformation to planar conformation in the crystals. In this research subjects, we will disclose the detailed pathway on the crystal-to-crystal transition and establish the principle for the design of novel emissive soft crystals based on the curved π-conjugated frameworks.

Emissive Soft Crystals based on Curved π-conjugated Framework


Academic papers/reviewed


  1. "Quadruply BN-Fused Tetrathia[8]circulenes with Flexible Frameworks: Synthesis, Structures and Properties" S. Akahori, T. Sasamori, H. Shinokubo, *Y. Miyake, Chem. Eur. J., 27, 8178-8184 (2021).
  2. "Synthesis of Tetrasilatetrathia[8]circulenes through C–I and C–H Silylation" S. Akahori, T. Fujihara, Y. Tsuji, H. Shinokubo, *Y. Miyake, Synthesis 53, 2995-3000 (2021).
  3. "Synthesis and Characterization of 16π Antiaromatic 2,7-Dihydrodiazapyrenes: Antiaromatic Polycyclic Hydrocarbons with Embedded Nitrogen" T. Nakazato, H. Takekoshi, T. Sakurai, H. Shinokubo, *Y. Miyake, Angew. Chem. Int. Ed. 60, 13877-13881 (2021).
  4. "Aggregation-Induced Emission in Tetrathia[8]circulene Octaoxides via Restriction of the Dynamic Motion of their Negatively Curved π-Frameworks" H. Murase, Y. Nagata, S. Akahori, H. Shinokubo, *Y. Miyake, Chem. Asian J., 15, 3873-3877 (2020).
  5. "Enthalpically and Entropically Favorable Self-Assembly: Synthesis of C4h-Symmetric Tetraazatetrathia[8]circulenes by Regioselective Introduction of Pyridine Rings" S. Akahori, T. Sasamori, H. Shinokubo, *Y. Miyake, Chem. Eur. 27, 5675-5682 (2021). (Highlighted at Inside Cover).
  6. "Complexation of 2,7-Diazapyrene with Boron for Structural and Electronic Tuning" T. Nakazato, H. Shinokubo, *Y. Miyake, Chem. Commun. 57, 327-330 (2021). (Highlighted at Inside Backcover)
  7. "Peripherally Arylated 2,8-Diazaperylenes from Anthracene Diimide: Synthesis and Oxidative Annulation" T. Sakurai, T. Nakazato, H. Shinokubo, *Y. Miyake, Org. Lett., 23, 2099-2103 (2021).

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