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A02 Takeharu Haino

Takeharu Haino

Participating A02

Affiliation

Department of Chemistry, Graduate School of Science, Hiroshima University

Position

Professor

Contact

haino＠hiroshima-u.ac.jp

HP

http://home.hiroshima-u.ac.jp/orgchem/

Research Project

Development of Dissymmetric Spaces formed via Molecular Recognition

Co-Investigator

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)

Abstract

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

Keywords

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

2021

[65] Programmed Dynamic Covalent Chemistry System of Addition-condensation Reaction of Phenols and Aldehydes,
Hiroto Kudo; Daisuke Shimoyama; Ryo Sekiya; Takeharu Haino, Chem. Lett., 50, 4, 825 – 831, 2021
DOI: 10.1246/cl.200773.
[64] Blueish-white-light-emitting Nanographenes Developed by Pd-Catalyzed Suzuki-Miyaura Cross Coupling Reactions,
Shohei Nishitani; Ryo Sekiya; Ikuya Matsumoto; Takeharu Haino, Chem. Lett., 50, 4, 664 – 667, 2021
DOI: 10.1246/cl.200844.
[63] Self-Assembling Behavior and Chiroptical Properties of Carbazole-Cored Phenyl Isoxazolyl Benzenes,
Yudai Ono; Takehiro Hirao; Toshiaki Ikeda; Takeharu Haino, J. Org. Chem., 86, 8, 5499 – 5505, 2021
DOI: 10.1021/acs.joc.0c03005.
[62] Helically organized fullerene array in a supramolecular polymer main chain,
Takehiro Hirao; Yoshiki Iwabe; Naoka Fujii; Takeharu Haino, J. Am. Chem. Soc., 143, 4339 – 4345, 2021
DOI: 10.1021/jacs.0c13326.
[61] Stereoselectivity in Dehydrative Cyclic Trimerization of Substituted 4-Alkylaminobenzoic Acids,
Koji Takagi; Hinako Yamaguchi; Daiki Miyamoto; Yuka Deguchi; Takehiro Hirao; Takeharu Haino, New Journal of Chemistry, 45, 1187 – 1193, 2021
DOI: 10.1039/D0NJ05368F.
[60] A Light-Harvesting/Charge-Separation Model with Energy Gradient Made of Assemblies of meta-pyridyl Zinc Porphyrins,
Joe Otsuki; Takumi Okumura; Kosuke Sugawa; Shin-ichiro Kawano; Kentaro Tanaka; Takehiro Hirao; Takeharu Haino; Yu Jin Lee; Seongsoo Kang; Dongho Kim, Chem. Eur. J., 27, 4053 – 4063, 2021
DOI: 10.1002/chem.202003327.
[59] Calix[4]arene‐Based Triple‐Stranded Metallohelicate in Water,
Masayuki Morie; Ryo Sekiya; Takeharu Haino, Chem. Asian. J., 16, 49 – 55, 2021
DOI: 10.1002/asia.202001154.
[58] Translational isomers of N-sulfonylated [3]catenane: synthesis and isomerization,
Hajime Iwamoto; Yuki Ishizu; Eietsu Hasegawa; Ryo Sekiya; Takeharu Haino, Chem. Commun., 57, 1915 – 1918, 2021
DOI: 10.1039/d0cc07720h.
[57] Folding and Unfolding of Acetoxy Group-Terminated Alkyl Chains Inside a Size Regulable Hemi-Carcerand,
Kentaro Harada; Ryo Sekiya; Takeharu Haino, J. Org. Chem., 86, 4440 – 4447, 2021
DOI: 10.1021/acs.joc.0c02833.
[56] Edge Functionalized Nanographenes,
Ryo Sekiya; Takeharu Haino, Chem. Eur. J., 27, 1, 187 – 199, 2021
DOI: 10.1002/chem.202003370.

2020

[55] Feet-to-Feet-Connected Multitopic Resorcinarene Macrocycles,
Daisuke Shimoyama; Takeharu Haino, Asian Journal of Organic Chemistry, 9, 1718 – 1725, 2020
DOI: 10.1002/ajoc.202000302.
[54] Conformation of K+(Crown Ether) Complexes Revealed by Ion Mobility–Mass Spectrometry and Ultraviolet Spectroscopy,
Sota Tainaka; Tomoyuki Ujihira; Mayuko Kubo, Mayuko; Motoki Kida; Daisuke Shimoyama; Satoru Muramatsu; Manabu Abe; Takeharu Haino; Takayuki Ebata; Fuminori Misaizu; Keijiro Ohshimo; Yoshiya Inokuchi, J. Phys. Chem. A, 124, 9980 – 9990, 2020
DOI: 10.1021/acs.jpca.0c09068.
[53] Self-Healing Supramolecular Materials Constructed by Copolymerization via Molecular Recognition of Cavitand-based Coordination Capsules,
Natsumi Nitta; Mei Takatsuka; Shin-ichi Kihara; Takehiro Hirao; Takeharu Haino, Angew. Chem. Int. Ed., 59, 16690 – 16697, 2020
DOI: 10.1002/anie.202006604.
[52] Absorption of Chemicals in Amorphous Trisresorcinarene,
Daisuke Shimoyama; Ryo Sekiya; Takeharu Haino, Chem. Commun., 56, 12582 – 12585, 2020
DOI: 10.1039/D0CC05066K.
[51] Chemically Functionalized Two-Dimensional Carbon Materials,
Ryo Sekiya; Takeharu Haino, Chem. Asian. J., 15, 15, 2316 – 2328, 2020
DOI: 10.1002/asia.202000196.
[50] One-dimensional arrangement of NORIA in the solid-state,
Daisuke Shimoyama; Ryo Sekiya; Hiroyuki Maekawa; Hiroto Kudo; Takeharu Haino, CrystEngComm, 22, 4740 – 4747, 2020
DOI: 10.1039/D0CE00650E.
[49] A dual redox-responsive supramolecular polymer driven by molecular recognition between bisporphyrin and trinitrofluorenone,
Naoyuki Hisano; Takehiro Hirao; Takeharu Haino, Chem. Commun., 56, 55, 7553 – 7556, 2020
DOI: 10.1039/D0CC02474K.
[48] Helicity of a polyacetylene directed by molecular recognition of biscalixarene and fullerene,
Takehiro Hirao; Yoshiki Iwabe; Naoyuki Hisano; Takeharu Haino, Chem. Commun., 56, 49, 6672 – 6675, 2020
DOI: 10.1039/D0CC02506B.
[47] Columnar Organization of Carbo[5]helicene Directed by Peripheral Steric Perturbation,
Takehiro Hirao; Yudai Ono; Naomi Kawata; Takeharu Haino, Org. Lett., 22, 14, 5294 – 5298, 2020
DOI: 10.1021/acs.orglett.0c01421.
[46] Construction of Helically Stacked π-Electron Systems in Poly(quinolylene-2,3-methylene) Stabilized by Intramolecular Hydrogen Bonds,
Yuki Kataoka; Naoya Kanbayashi; Naoka Fujii; Taka-aki Okamura; Takeharu Haino; Kiyotaka Onitsuka, Angew. Chem. Int. Ed., 59, 26, 10286 – 10291, 2020
DOI: 10.1002/anie.202002734.
[45] AIE-active micelles formed by self-assembly of an amphiphilic platinum complex possessing isoxazole moieties,
Takehiro Hirao; Hidemi Tsukamoto; Toshiaki Ikeda; Takeharu Haino, Chem. Commun., 56, 1137 – 1140, 2020
DOI: 10.1039/C9CC07819C.
[44] A Regulable Internal Cavity Inside A Resorcinarene-Based Hemi-Carcerand,
Kentaro Harada; Ryo Sekiya; Takeharu Haino, Chem. Eur. J., 26, 5810 – 5817, 2020
DOI: 10.1002/chem.201905805.
[43] A Supramolecular Approach to Polymer-Shape Transformation via Calixarene-Fullerene Complexation,
Takehiro Hirao; Kazushi Fukuta; Takeharu Haino, Macromolecules, 53, 9, 3563 – 3570, 2020
DOI: 10.1021/acs.macromol.0c00621.
[42] Supramolecular Polymerization and Functions of Isoxazole Ring Monomers,
Takeharu Haino; Takehiro Hirao, Chem. Lett., 49, 574 – 584, 2020
DOI: 10.1246/cl.200031.
[41] Upper-Rim Functionalization and Supramolecular Polymerization of a Feet-to-Feet-Connected Biscavitand,
Daisuke Shimoyama; Ryo Sekiya; Takeharu Haino, Chem. Commun., 56, 3733 – 3736, 2020
DOI: 10.1039/D0CC00933D.
[40] Folding Control of Non-natural Glycopeptide Using Saccharide-coded Structural Information for Polypeptide,
Yuki Ishido; Naoya Kanbayashi; Naoka Fujii; Taka-aki Okamura; Takeharu Haino; Kiyotaka Onitsuka, Chem. Commun., 56, 2767 – 2770, 2020
DOI: 10.1039/C9CC10030J.
[39] Entropy–driven Cooperativity in the Guest Binding of an Octaphosphonate Biscavitand,
Daisuke Shimoyama; Takeharu Haino, Chem. Eur. J., 26, 3074 – 3079, 2020
DOI: 10.1002/chem.201905036.
[38] Chirality-Embedded Nanographenes,
Shohei Nishitani; Ryo Sekiya; Takeharu Haino, Angew. Chem. Int. Ed., 59, 2, 669 – 673, 2020
DOI: 10.1002/anie.201910040.
[37] Feet-to-Feet Connected Trisresorcinarenes,
Daisuke Shimoyama; Ryo Sekiya; Hiroto Kudo; Takeharu Haino, Org. Lett., 22, 352 – 356, 2020
DOI: 10.1021/acs.orglett.9b03693.

2019

[36] Separation of Spectroscopically Uniform Nanographenes,
Kairi Yamato; Ryo Sekiya; Manabu Abe; Takeharu Haino, Chem. Asian. J., 14, 10, 1786 – 1791, 2019
DOI: 10.1002/asia.201801632.
[35] Intrinsic Emission from Nanographenes,
Kairi Yamato; Ryo Sekiya; Shohei Nishitani; Takeharu Haino, Chem. Asian. J., 14, 18, 3213 – 3220, 2019
DOI: 10.1002/asia.201900906.
[34] Conformational Characteristics of Feet-to-Feet-Connected Biscavitands,
Daisuke Shimoyama; Takeharu Haino, J. Org. Chem., 84, 21, 13483 – 13489, 2019
DOI: 10.1021/acs.joc.9b01730.
[33] Organogelators of 5,17-Difunctionalized Calix[4]arenes,
Lai Nang Duy; Ryo Sekiya; Masatoshi Tosaka; Shigeru Yamago; Takuya Matsumoto; Takashi Nishino; Takayuki Ichikawa; Takeharu Haino, Chem. Lett., 48, 43 – 46, 2019
DOI: 10.1246/cl.180819.
[32] Designer Supramolecular Polymers with Specific Molecular Recognitions,
Takeharu Haino, Polymer Journal, 51, 303 – 318, 2019
DOI: 10.1038/s41428-018-0126-7.
[31] Near‐Infrared‐Emitting Nitrogen‐Doped Nanographenes,
Kairi Yamato; Ryo Sekiya; Kaho Suzuki; Takeharu Haino, Angew. Chem. Int. Ed., 58, 27, 9022 – 9026, 2019
DOI: 10.1002/anie.201901510.
[30] A protocol for size separation of nanographenes,
Ikuya Matsumoto; Ryo Sekiya; Takeharu Haino, RSC Adv., 9, 58, 33843 – 33846, 2019
DOI: 10.1039/c9ra07528c.
[29] Tunable enforced cavities inside self-assembled capsules,
Takeshi Maehara; Ryo Sekiya; Kentaro Harada; Takeharu Haino, Organic Chemistry Frontiers, 6, 10, 1561 – 1566, 2019
DOI: 10.1039/c9qo00010k.
[28] Ring–Chain Competition in Supramolecular Polymerization Directed by Molecular Recognition of the Bisporphyrin Cleft,
Takehiro Hirao; Naoyuki Hisano; Shigehisa Akine; Shin-ichi Kihara; Takeharu Haino, Macromolecules, 52, 16, 6160 – 6168, 2019
DOI: 10.1021/acs.macromol.9b01012.
[27] Helical Assembly of a Dithienogermole Exhibiting Switchable Circularly Polarized Luminescence,
Kyohei Hirano; Toshiaki Ikeda; Naoka Fujii; Takehiro Hirao; Masashi Nakamura; Yohei Adachi; Joji Ohshita; Takeharu Haino, Chem. Commun., 55, 71, 10607 – 10610, 2019
DOI: 10.1039/C9CC05253D.
[26] Substituent-controlled racemization of dissymmetric coordination capsules,
Kentaro Harada; Ryo Sekiya; Takeshi Maehara; Takeharu Haino, Organic & Biomolecular Chemistry, 17, 19, 4729 – 4735, 2019
DOI: 10.1039/C9OB00388F.

2018

[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 via Coordination-Driven Self-Assembly of a Four-Armed Cavitand,
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, 18, 4960 – 4964, 2018
DOI: 10.1002/anie.201713299.

2017

[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.

2016

[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.