A02 Takeharu Haino

Takeharu Haino

Participating A02


Department of Chemistry, Graduate School of Science, Hiroshima University





Research Project

Development of Dissymmetric Spaces formed via Molecular Recognition


Ryo Sekiya (Associate Pofessor, Department of Chemistry, Graduate School of Science, Hiroshima University)

Toshiaki Ikeda (Assistant Professor, Department of Chemistry, Graduate School of Science, Tokai University)


Our group has been developing calixarene-based hosts that display unique molecular recognition. During the course of these studies, we have developed dissymmetric calixarene capsules via coordination-driven self-assembly. The capsules existed as a racemic mixture of the (P)- and (M)-enantiomeric forms which are dynamically interconvertible through dissociation and recombination. When chiral guests are captured, the chiral interiors recognize the shape of the guests, which results in a difference in energy between the diastereomeric complexes. However, the removal of chiral guests results in the quick racemization. We envisage developing supramolecular helical polymeric capsules that possess multiple guest binding sites being coupled together. Chiral guest binding can cooperatively participate in the chiral induction of the helical organization of the supramolecular polymeric capsules that could be applied for chiral separation and catalytic systems.

Research Areas

Supramolecular Chemistry, Polymer chemistry, Organic Chemistry


Self-Assembly, Supramolecular Capsule, Chiral Recognition, Supramolecular Polymer, Helicate


[25] A circularly polarized luminescent organogel based on a Pt(ii) complex possessing phenylisoxazoles,
Toshiaki Ikeda; Kyohei Hirano; Takeharu Haino, Materials Chemistry Frontiers, 2, 468 - 474, 2018
DOI: 10.1039/c7qm00564d.
[24] Facile Synthesis of an Eight-Armed Star-Shaped Polymer,
Natsumi Nitta; Mei Takatsuka; Shin-ichi Kihara; Ryo Sekiya; Takeharu Haino, ACS Macro Letters, 7, 1308 - 1311, 2018
DOI: 10.1021/acsmacrolett.8b00669.
[23] Majority-Rules Effect and Allostery in Molecular Recognition of Calix[4]arene-Based Triple-Stranded Metallohelicates,
Yutaro Yamasaki; Hidemi Shio; Tomoko Amimoto; Ryo Sekiya; Takeharu Haino, Chem. Eur. J., 24, 34, 8558 - 8568, 2018
DOI: 10.1002/chem.201800997.
[22] Controllable Direction of Porphyrin Derivatives in Two Cyclodextrin Cavities,
Banri Horiguchi; Toshimi Nakaya; Masafumi Ueda; Kouta Sugikawa; Tsutomu Mizuta; Takeharu Haino; Naomi Kawata; Atsushi Ikeda, European Journal of Organic Chemistry, 2018, 18, 2138 - 2143, 2018
DOI: 10.1002/ejoc.201800433.
[21] Pseudorotaxanes in the Gas Phase: Structure and Energetics of Protonated Dibenzylamine–Crown Ether Complexes,
Motoki Kida; Daisuke Shimoyama; Toshiaki Ikeda; Ryo Sekiya; Takeharu Haino; Takayuki Ebata; Christophe Jouvet; Yoshiya Inokuchi, Phys. Chem. Chem. Phys., 20, 27, 18678 - 18687, 2018
DOI: 10.1039/c8cp02707b.
[20] Supramolecular Copolymerization via Sequence Reorganization of Supramolecular Homopolymer,
Kouhei Nadamoto; Kei Maruyama; Naoka Fujii; Toshiaki Ikeda; Shin-ichi Kihara; Takeharu Haino, Angew. Chem. Int. Ed., 57, 7028 - 7033, 2018
DOI: 10.1002/ange.201800980.
[19] Supramolecular Polymer Network of Graphene Quantum Dots,
Yuichiro Uemura; Kairi Yamato; Ryo Sekiya; Takeharu Haino, Angew. Chem. Int. Ed., 57, , 2018
DOI: 10.1002/anie.201713299.


[18] Synthesis and Structure of Feet-to-Feet Connected Bisresorcinarenes,
Daisuke Shimoyama; Toshiaki Ikeda; Ryo Sekiya; Takeharu Haino, J. Org. Chem., 82, 13220 - 13230, 2017
DOI: 10.1021/acs.joc.7b02301.
[17] Slow Intermolecular Complexation–Decomplexation Exchanges of Cyclodextrins in Fullerene and Its Derivative Complexes,
Atsushi Ikeda; Tomoya Mae; Kouta Sugikawa; Kenji Komaguchi; Toshifumi Konishi; Takehiro Hirao; Takeharu Haino, Chemistryselect, 2, 34, 11322 - 11327, 2017
DOI: 10.1002/slct.201702319.
[16] Hexameric assembly of 5,17-di-substituted calix[4]arene in the solid state,
Yutaro Yamasaki; Ryo Sekiya; Takeharu Haino, CrystEngComm, 19, 6744, 6744 - 6751, 2017
DOI: 10.1039/C7CE01515A.
[15] Supramolecular Polymeric Assemblies of π-Conjugated Molecules Possessing Phenylisoxazoles,
Toshiaki Ikeda; Takeharu Haino, Polymer, 128, 243 - 256, 2017
DOI: 10.1016/j.polymer.2017.02.059.
[14] Sequence-controlled Supramolecular Terpolymerization Directed by Specific Molecular Recognitions,
Takehiro Hirao; Hiroaki Kudo; Tomoko Amimoto; Takeharu Haino, Nat. Commun., 8, 634 - 634, 2017
DOI: 10.1038/s41467-017-00683-5.
[13] Induced Dipole-Directed, Cooperative Self-Assembly of a Benzotrithiophene,
Toshiaki Ikeda; Hiroaki Adachi; Hiroyuki Fueno; Kazuyoshi Tanaka; Takeharu Haino, J. Org. Chem., 82, , 2017
DOI: 10.1021/acs.joc.7b01520.
[12] Light-Harvesting Organogel based on Tris(phenylisoxazolyl)benzene,
Toshiaki Ikeda; Yuko Ueda; Naomitsu Komori; Manabu Abe; Takeharu Haino, Supramol. Chem., 29, 6, 471 - 476, 2017
DOI: 10.1080/10610278.2016.1268692.
[11] Photoluminescent Responses of Graphene Quantum Dots toward Organic Bases and an Acid,
Kaho Suzuki; Kairi Yamato; Ryo Sekiya; Takeharu Haino, Photochem. Photobiol. Sci., 16, 5, 623 - 626, 2017
DOI: 10.1039/c7pp00067g.
[10] Supramolecular Graft Copolymerization of a Polyester by Guest-Selective Encapsulation of a Self-Assembled Capsule,
Yuta Tsunoda; Mei Takatsuka; Ryo Sekiya; Takeharu Haino, Angew. Chem. Int. Ed., 56, 10, 2613 - 2618, 2017
DOI: 10.1002/anie.201611394.


[9] Photoresponsive Toroidal Nanostructure Formed by Self-Assembly of Azobenzene-Functionalized Tris(phenylisoxazolyl)benzene,
Hiroaki Adachi; Yuko Hirai; Toshiaki Ikeda; Makoto Maeda; Ryo Hori; Shoichi Kutsumizu; Takeharu Haino, Org. Lett., 18, 5, 924 - 927, 2016
DOI: 10.1021/acs.orglett.5b03622.
[8] Cooperative Self-Assembly of Carbazole Derivative Driven by Multiple Dipole–Dipole Interactions,
Toshiaki Ikeda ; Tatsuya Iijima; Ryo Sekiya; Osamu Takahashi; Takeharu Haino, J. Org. Chem., 81, 15, 6832 - 6837, 2016
DOI: 10.1021/acs.joc.6b01169.
[7] Solvent-Induced Emission of Organogels Based on Tris(Phenylisoxazolyl)Benzene,
Toshiaki Ikeda; Tetsuya Masuda; Midori Takayama; Hiroaki Adachi; Takeharu Haino, Org. Biomol. Chem., 14, 1, 36 - 39, 2016
DOI: 10.1039/c5ob01898f.
[6] Frozen Dissymmetric Cavities in Resorcinarene-BasedCoordination Capsules,
Taisuke Imamura; Takeshi Maehara; Ryo Sekiya; Takeharu Haino, Chem. Eur. J., 22, 10, 3250 - 3254, 2016
DOI: 10.1002/chem.201505183.
[5] Synthesis of Linear [5]Catenanes via Olefin Metathesis Dimerization of Pseudorotaxanes Composed of a [2]Catenane and a Secondary Ammonium Salt,
Hajime Iwamoto; Shinji Tafuku; Yoshihiko Sato; Wataru Takizawa; Wataru Katagiri; Eiji Tayama; Eietsu Hasegawa; Yoshimasa Fukazawa; Takeharu Haino, Chem. Commun., 52, 2, 319 - 322, 2016
DOI: 10.1039/c5cc07562a.
[4] Hydrogen-Bonded Hexameric Cluster of Benzyl Alcohol in the Solid State Polymeric Organization of p-tert-Butylcalix[5]arene,
Yasunori Kajiki; Ryo Sekiya; Takeharu Haino, Supramol. Chem., 28, 5-6, 444 - 449, 2016
DOI: 10.1080/10610278.2015.1117084.
[3] Induced-Fit Molecular Recognition of Alkyl Chains in p-tert-Butylcalix[5]arene in the Solid State,
Yasunori Kajiki; Ryo Sekiya; Yutaro Yamasaki; Yuichiro Uemura; Takeharu Haino, Bull. Chem. Soc. Jpn., 89, 2, 220 - 225, 2016
DOI: 10.1246/bcsj.20150344.
[2] Allostery in Guest Binding of Rim-to-Rim Connected Homoditopic Biscavitands,
Daisuke Shimoyama; Hitomi Yamada; Toshiaki Ikeda; Ryo Sekiya; Takeharu Haino, Eur. J. Org. Chem., 20, 3300 - 3303, 2016
DOI: 10.1002/ejoc.201600410.
[1] Chemical Functionalization and Photoluminescence of Graphene Quantum Dots,
Ryo Sekiya; Yuichiro Uemura; Hiroyoshi Naito; Kensuke Naka; Takeharu Haino, Chem. Eur. J., 22, 24, 8198 - 8206, 2016
DOI: 10.1002/chem.201504963.