Tomoki Ogoshi

Graduate School of Engineering, Kyoto University
Professor
A01
Research AreasSupramolecular Chemistry, Polymer Chemistry
Participating Group (2020-2021)

Construction of Selective Responsive Soft Crystals by Weak-stimuli Based on Pillar-Shaped Macrocyclic Compounds

Keywords
Host-guest Complexes, Soft Crystals, Macrocyclic Compounds, Weak-stimuli Responsive, Pillar[n]arenes
Co-Researcher
Co-Researcher: Fa Shixin (Graduate School of Engineering, Kyoto University, Assistant professor)

Research Outline

To develop designed soft crystals, it is important to clarify how external stimuli input into soft crystals and the soft crystals exhibit the response. This researcher has developed pillar-shaped macrocyclic compounds “pillar[n]arenes” （Structure of pillar[n]arenes）. Pillar[n]arenes form host-guest complexes with alkane vapors because of their electron rich cavity. But, pillar[n]arene crystals are colorless solids; thus, we cannot detect encapsulation of alkane vapor. We have discovered that crystals of functionalized pillar[n]arene which contains one benzoquinone unit that endows the molecule with alkane-vapor-induced vapochromic properties (Vapochromic behavior of pillar[5]arene with one benzoquinone unit). In this study, we will expand soft crystal chemistry using pillar[n]arenes. The research subjects are (1) development of pillar[n]arene with vapor-responsive fluorescence by introducing -conjugated units into pillar[n]arenes and (2) chiral vapor detection using planar chirality of pillar[n]arenes

Structure of pillar[n]arenes
Vapochromic behavior of pillar[5]arene with one benzoquinone unit

Participating Group (2018-2019)

Construction of Weak-stimuli Responsive Soft Crystals Based on Pillar-Shaped Macrocyclic Compounds

Keywords
Host-guest Complexes, Soft Crystals, Macrocyclic Compounds, Weak-stimuli Responsive, Pillar[n]arenes
Co-Researcher
Co-Researcher: Takahiro Kakuta (Institute of Science and Engineering, Kanazawa University, Assistant Professor)

Research Outline

To develop designed soft crystals, it is important to clarify how external stimuli input into soft crystals and the soft crystals exhibit the response. This researcher has developed pillar-shaped macrocyclic compounds “pillar[n]arenes” （Structure of pillar[n]arenes）. Pillar[n]arenes form host-guest complexes with alkane vapors because of their electron rich cavity. But, pillar[n]arene crystals are colorless solids; thus, we cannot detect encapsulation of alkane vapor. We have discovered that crystals of functionalized pillar[n]arene which contains one benzoquinone unit that endows the molecule with alkane-vapor-induced vapochromic properties (Vapochromic behavior of pillar[5]arene with one benzoquinone unit). In this study, we will expand soft crystal chemistry using pillar[n]arenes. The research subjects are (1) development of pillar[n]arene with vapor-responsive fluorescence by introducing -conjugated units into pillar[n]arenes and (2) chiral vapor detection using planar chirality of pillar[n]arenes

Structure of pillar[n]arenes
Vapochromic behavior of pillar[5]arene with one benzoquinone unit

Publications

Academic papers/reviewed

A01-16

  1. "Vapoluminescence Behavior Triggered by Crystal-State Complexation between Host Crystals and Guest Vapors Exhibiting No Visible Fluorescence" T. Ogoshi, Y. Hamada, R. Sueto, R. Kojima, F. Sakakibara, Y. Nagata, Y. Sakata, S. Akine, T. Ono, T. Kakuta and T. Yamagishi, Cryst. Growth Des., 2020, 20(11), 7087-7092
    DOI: 10.1021/acs.cgd.0c00982
  2. "Sequential Chiral Induction and Regulator‐Assisted Chiral Memory of Pillar[5]arenes" S. Fa, K. Egami, K. Adachi, K. Kato and T. Ogoshi, Angewandte Chemie, International Edition, 2020, 59(46), 20353-20356
    DOI: 10.1002/anie.202010050
  3. "Host–Guest Complexation Using Pillar[5]arene Crystals: Crystal-Structure Dependent Uptake, Release, and Molecular Dynamics of an Alkane Guest" T. Ogoshi, Y. Hamada, R. Sueto, Y. Sakata, S. Akine, A. M. P. Moeljadi, H. Hirao, T. Kakuta, T. Yamagishi, M. Mizuno, Chemistry – A European Journal, 2019, 25, 2497-2502.
    DOI: 10.1002/chem.201900220
  4. "Metallonanobelt: A Kinetically Stable Shape-Persistent Molecular Belt Prepared by Reversible Self-Assembly Processes" Y. Sakata, R. Yamamoto, D. Saito, Y. Tamura, K. Maruyama, T. Ogoshi, S. Akine, Inorg. Chem., 2018, 57, 15500-15506.
    DOI: 10.1021/acs.inorgchem.8b02804
  5. "Guest Vapor-Induced State Change of Structural Liquid Pillar[6]arene" T. Ogoshi, K. Maruyama, Y. Sakatsume, T. Kakuta, T. Yamagishi, T. Ichikawa, M. Mizuno, J. Am. Chem. Soc., 2019, 141, 785-789.
    DOI: 10.1021/jacs.8b12253
  6. "Molecular weight fractionation by confinement of polymer in one-dimensional pillar[5]arene channels" T. Ogoshi, R. Sueto, M. Yagyu, R. Kojima, T. Kakuta, T. Yamagishi, K. Doitomi, A. K. Tummanapelli, H. Hirao, Y. Sakata, S. Akine, M. Mizuno, Nature Commun., 2019, 10, 479.
    DOI: 10.1038/s41467-019-08372-1
  7. "Applications of Pillar[n]arene-Based Supramolecular Assemblies" T. Ogoshi, T. Kakuta, T. Yamagishi, Angew. Chem. Int. Ed., 2019, 58, 2197-2206.
    DOI: 10.1002/anie.201805884
  8. "Stimuli-Responsive Supramolecular Assemblies Constructed from Pillar[n]arenes" T. Kakuta, T. Yamagishi, T. Ogoshi, Acc. Chem. Res., 2018, 51, 1656-1666.
    DOI: 10.1021/acs.accounts.8b00157
  9. "A Planar-Chiral Pillar[5]arene-Based Monophosphine Ligand with Induced Chirality at the Biaryl Axis" Y. Nagata, Y. Shimada, T. Nishikawa, R. Takeda, M. Uno, T. Ogoshi, M. Suginome, Synlett, 2018, 29, 2167-2170.
    DOI: 10.1055/s-0037-1610635
  10. "An amphiphilic pseudo[1]catenane: neutral guest-induced clouding point change" T. Ogoshi, T. Akutsu, T. Yamagishi, Beilstein J. Org. Chem., 2018, 14, 1937-1943.
    DOI: 10.3762/bjoc.14.167
Contact
ogoshi[at]sbchem.kyoto-u.ac.jp