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. "Reversible “On/Off” Chiral Amplification of Pillar[5]arene Assemblies by Dual External Stimuli" S. Fa, M. Mizobata, S. Nagano, K. Suetsugu, T. Kakuta, T. Yamagishi, *T. Ogoshi, ACS Nano 15, 16794–16801 (2021).
    DOI: 10.1021/acsnano.1c06975
  2. "Thermally Responsive Poly(ethylene oxide)-based Polyrotaxanes Bearing Hydrogen-bonding Pillar[5]arene Rings" K. Kato, K. Onishi, K. Maeda, M. Yagyu, S. Fa, T. Ichikawa, M. Mizuno, T. Kakuta, T. Yamagishi, *T. Ogoshi, Chem. Eur. J.,27(21), 6435-6439(2021). (Cover) (領域内共同研究 A01公募 水野)
    DOI: 10.1002/chem.202005099
  3. "Pre-regulation of the Planar Chirality of Pillar[5]arenes for Preparing Discrete Chiral Nanotubes" S. Fa, K. Adachi, Y. Nagata, E. Egami, K. Kato, *T. Ogoshi, Chem. Sci., 2021,12, 3483-3488.
    DOI: 10.1039/D1SC00074H
  4. "Biomimetic Approach for Highly Selective Artificial Water Channels Based on Tubular Pillar[5]Arene Dimers" D. Strilets, S. Fa, A. Hardiagon, M. Baaden, *T. Ogoshi, *M. Barboiu, Angew. Chem. Int. Ed., 59, 23213-23219 (2020).
    DOI: 10.1002/anie.202009219
  5. "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, T. Yamagishi, Cryst. Growth Des., 20, 7087-7092 (2020). (Supplementary Cover) (領域内共同研究　A01公募 酒田, A02小野)
    DOI: 10.1021/acs.cgd.0c00982
  6. "Sequential Chiral Induction and Regulator-Assisted Chiral Memory of Pillar[5]arenes" S. Fa, K. Egami, K. Adachi, K. Kato, *T. Ogoshi, Angew. Chem. Int. Ed., 58, 20353-20356 (2020). (Inside Back Cover)
    DOI: 10.1002/anie.202010050
  7. "Holding of Planar Chirality of Pillar[5]arene by Kinetic Trapping Using Host-Guest Interactions with Achiral Guest Solvents" *Y. Nagata, M. Suzuki, Y. Shimada, H. Sengoku, S. Nishida, T. Kakuta, T. Yamagishi, *M. Suginome, *T. Ogoshi, Chem. Commun., 56, 8424-8427 (2020).
    DOI: 10.1002/anie.201916515
  8. "Guest Exchangeable Length-Controlled Discrete Tubes via Non-Covalent Interactions" S. Fa, Y. Sakata, S. Akine, *T. Ogoshi, Angew. Chem. Int. Ed., 58, 2197-2206 (2020). (領域内共同研究 A01公募 酒田)
    DOI: 10.1002/anie.201916515
  9. "Obvious Vapochromic Color Changes of a Pillar[6]arene Containing One Benzoquinone Unit with a Mechanochromic Change Before Vapor Exposure" K. Wada, T. Kakuta, T. Yamagishi, *T. Ogoshi, Chem. Commun., 56, 4344-4347 (2020).
    DOI: 10.1039/D0CC01112F
  10. "Conformation and Planar Chirality of Pillar[n]arenes" S. Fa, T. Kakuta, T. Yamagishi, *T. Ogoshi, Chem. Lett., 48, 1278-1287 (2019). (Cover)
    DOI: 10.1246/cl.190544
  11. "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, Chem. Eur. J., 25, 2497-2502 (2019). (Cover)(領域内共同研究 A01公募 酒田)
    DOI: 10.1002/chem.201805733
  12. "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., 141, 785-789 (2019).
    DOI: 10.1021/jacs.8b12253
  13. "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., 10479 (2019). (領域内共同研究　A01公募 酒田)
    DOI: 10.1038/s41467-019-08372-1
  14. "Applications of Pillar[n]arene-Based Supramolecular Assemblies" *T. Ogoshi, T. Kakuta, T. Yamagishi, Angew. Chem. Int. Ed., 58, 2197-2206 (2019).
    DOI: 10.1002/anie.201805884
  15. "Stimuli-Responsive Supramolecular Assemblies Constructed from Pillar[n]arenes" T. Kakuta, T. Yamagishi, *T. Ogoshi, Acc. Chem. Res., 51, 1656-1666 (2018).
    DOI: 10.1021/acs.accounts.8b00157
  16. "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, 29, 2167-2170 (2018).
    DOI: 10.1055/s-0037-1610635
  17. "An amphiphilic pseudo[1]catenane: neutral guest-induced clouding point change" *T. Ogoshi, T. Akutsu, T. Yamagishi, Beilstein J. Org. Chem., 14, 1937-43
    DOI: 10.3762/bjoc.14.167
  18. "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, 29, 2167-2170 (2018).

International conferences

A01-16

  1. Tomoki Ogoshi “Pillar-Shaped Macrocyclic Compounds “Pillar[n]arenes”: from Simple Molecular Receptors to Bulk Supramolecular Assemblies”, SCEJ 86th Annual Meeting, International Symposium, Japan, Online, 2021/3/20.
  2. Tomoki Ogoshi “Pillar-Shaped Macrocyclic Compounds “Pillar[n]arenes”: from Simple Molecular Receptors to Supramolecular Assemblies”,ISMSC-2021 (Online), Prof. Shionoya 2020 Izatt-Christensen Award Session, University of Oregon, Oregon, US, Online, 2021/7/13.
  3. Tomoki Ogoshi “Pillar-Shaped Macrocyclic Compounds “Pillar[n]arenes”: from Simple Molecular Receptors to Supramolecular Assemblies”,UGe Organic Chemistry Lectures 2021, University of Geneva, Hosted by Prof. Jérôme Lacour, Geneva, Switzerland, Online, 2021/4/22.
  4. Tomoki Ogoshi “Supramolecular Assemblies of Pillar[n]arenes for Molecular Separation, Artificial Water Channels and Biosensor Applications”, 4th NanoLSI Symposium, Kanazawa University, Kanazawa, Japan, Online, 2020/11/26
Contact
ogoshi[at]sbchem.kyoto-u.ac.jp