Research Theme

Design and synthesis of three-dimensional organic structures

Keywords

π-conjugated molecules, molecular topology, 3D network polymer

Aromatic compounds are potentially useful as functional electronic materials. However, the design and control of three-dimensional molecular assembly are still very difficult, especially for the crystal engineering of organic molecules. This group aims to create novel topological and reticular organic structures by using synthetic organic chemistry and geometric insight. To achieve our purpose, this group will start electron-diffraction crystallography (MicroED) for the rapid structure determination of three-dimensional covalent organic frameworks.

1) Design and synthesis of π-conjugated organic molecules
2) Development of novel molecular topology
3) Construction of 3D network polymers

Selected Publications

1. Synthesis, structure, and properties of a bay-fluorinated triphenylene
   Ryu Yoshida, Haruki Sugiyama, Yasutomo Segawa*
   Chem. Lett. 2024, 53, upae048.
2. Synthesis of Polycyclic Arenes Composed of Four-, Five-, Six-, and Eight-Membered Rings via an Unexpected Four-Membered Ring Formation Reaction
   Soshi Hirota, Sachiko Nakano, Haruki Sugiyama, Yasutomo Segawa*
   Org. Lett. 2023, 25, 8062–8066.
3. Synthesis of penta- and hexa(3,4-thienylene): Size-dependent structural properties of cyclic oligothiophenes
   Mai Nagase, Sachiko Nakano, Yasutomo Segawa*
   Chem. Commun. 2023, 59, 11129-11132.
4. Nonplanar Aromatic Hydrocarbons: Design and Synthesis of Highly Strained Structures
   Yasutomo Segawa*
   Bull. Chem. Soc. Jpn. 2022, 95, 1600–1610.
5. Synthesis of a Möbius carbon nanobelt
   Yasutomo Segawa,* Tsugunori Watanabe, Kotono Yamanoue, Motonobu Kuwayama, Kosuke Watanabe, Kenichiro Itami*
   Nature Synth. 2022, 1, 535–541.
6. Double-helix supramolecular nanofibers assembled from negatively curved nanographenes
   Kenta Kato, Kiyofumi Takaba, Saori Maki-Yonekura, Nobuhiko Mitoma, Yusuke Nakanishi, Taishi Nishihara, Taito Hatakeyama, Takuma Kawada, Yuh Hijikata, Jenny Pirillo, Lawrence T. Scott, Koji Yonekura,* Yasutomo Segawa,* Kenichiro Itami*
   J. Am. Chem. Soc. 2021, 143, 5465-5469.
7. Synthesis of a zigzag carbon nanobelt
   Kwang Yin Cheung, Kosuke Watanabe, Yasutomo Segawa,* Kenichiro Itami*
   Nature Chem. 2021, 13, 255-259.
8. Topological Molecular Nanocarbons: All-benzene Catenane and Trefoil Knot
   Yasutomo Segawa,* Motonobu Kuwayama, Yuh Hijikata, Masako Fushimi, Taishi Nishihara, Jenny Pirillo, Junya Shirasaki, Natsumi Kubota, Kenichiro Itami*
   Science 2019, 365, 272-276.
9. Synthesis of a Carbon Nanobelt
   Guillaume Povie, Yasutomo Segawa,* Taishi Nishihara, Yuhei Miyauchi, Kenichiro Itami*
   Science 2017, 356, 172–175.
10. Metal-free Hydrogenation Catalysis of Polycyclic Aromatic Hydrocarbons
    Yasutomo Segawa, Douglas W. Stephan*
    Chem. Commun. 2012, 48, 11963–11965.
11. Boryllithium: Isolation, Characterization, and Reactivity as a Boryl Anion.
    Yasutomo Segawa, Makoto Yamashita,* Kyoko Nozaki*
    Science 2006, 314, 113–115.