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Kodama Lab.

埼玉大学大学院理工学研究科 物質科学専攻 応用化学プログラム
埼玉大学工学部 応用化学科 有機工業化学研究室（小玉研究室）
埼玉大学大学院理工学研究科 物質科学専攻 応用化学プログラム
埼玉大学工学部 応用化学科 有機工業化学研究室（小玉研究室）

研究業績

2025

  1. Koichi Kodama, Yumi Kondo and Takuji Hirose
    "Solvent-induced chirality switching in the enantioseparation of hydroxycarboxylic acids with a quaternary stereogenic center"
    ACS Omega, 2025, 10, 12129-12134. (open access)

2024

  1. Koichi Kodama, Masato Obata and Takuji Hirose
    "Enantioseparation via Chiral Supramolecular Gels Comprising Ambidextrous Gelators Based on β-Peptide-type Primary Amines"
    ChemPlusChem, 2024, 89, e202400021. (open access) (Selected as a Front Cover)

    (This work was supported by JSPS KAKENHI Grant Number JP23K04716.)

  2. Koichi Kodama, Yumi Kondo, Kosei Katayama, Moeka Yanagisawa and Takuji Hirose
    "Enantiomer separation of 2-halomandelic acids via diastereomeric salt formation with chiral N-substituted 2-amino-2-phenylethanols"
    Chirality, 2024, 36, e23630.

2023

  1. Takuji Hirose, Yuka Kikuchi, Tomoaki Nakano, Tsukasa Ohno, Kengo Kawamura, Normazliana Binti Nazri, Atsuhiro Fujimori, Koichi Kodama and Mikio Yasutake
    "Thermoreversible Helical Fibers from Photoreactive Triphenylene-Derived Liquid Crystals in Liquid Paraffin"
    Heliyon, 2023, 9, e22037. (open access)
  2. Jyorthana Rajappa Muralidhar, Krishnachary Salikolimi, Kiyohiro Adachi, Daisuke Hashizume, Koichi Kodama, Takuji Hirose, Yoshihiro Ito, and Masuki Kawamoto
    "Chemical Storage of Ammonia through Dynamic Structural Transformation of a Hybrid Perovskite Compound"
    J. Am. Chem. Soc., 2023, 145, 16973-16977.
    埼玉大学からプレスリリースを行いました。
  3. Koichi Kodama, Masato Obata, Sho Sugimura, Hiroki Yuhara and Takuji Hirose
    "Development of Low-Molecular-Weight Organogelators from Cyclic beta-Amino Acid: Effect of Stereochemistry and their Application on Visual Chiral Recognition of Amines"
    Chem. Eur. J., 2023, 29, e202202692.
  4. Srinivas Chandrasekaran, Masaki Tambo, Yuta Yamazaki, Tatsuro Muramatsu, Yusuke Kanda, Takuji Hirose and Koichi Kodama
    "Enantioseparation of 3-hydroxycarboxylic acids via diastereomeric salt formation by 2-amino-1,2-diphenylethanol (ADPE) and cinchonidine"
    Molecules, 2023, 28, 114. (open access)

2022

  1. Hayato Kanai, Kuniyo Yamada, Krishnachary Salikolimi, Koichi Kodama and Yasuhiro Ishida
    "Supramolecular Architecture of an Amphiphilic Amino Alcohol as a Versatile Chiral Environment for Stereocontrolled Photoreaction of Various Anthracenes"
    Chem. Eur. J., 2022, 28, e202201940. (Selected as Hot Paper)
  2. Koichi Kodama, Kazuhisa Maruyama and Takuji Hirose
    "Chiral 1,3-aminosquaramides derived from cis-2-benzamidocyclohexanecarboxylic acid as organocatalysts for asymmetric Michael addition reactions"
    Tetrahedron, 2022, 112, 132750.
  3. Srinivas Chandrasekaran, Takuji Hirose and Koichi Kodama
    ""Solvent-Induced Chirality Switching" in the Enantioseparation of Chlorine-Substituted Tropic Acids via Diastereomeric Salt Formation by (1R,2S)-(-)-2-amino-1,2-diphenylethanol (ADPE)"
    Tetrahedron, 2022, 108, 132653.
  4. Jyorthana Rajappa Muralidhar, Koichi Kodama, Takuji Hirose, Yoshihiro Ito and Masuki Kawamoto
    "Noncovalent Functionalization of Single-Walled Carbon Nanotubes with a Photocleavable Polythiophene Derivative"
    Nanomaterials, 2022, 12, 52.
  5. Hayato Kanai, Kuniyo Yamada, Koichi Kodama and Yasuhiro Ishida
    "Efficient preparation of stereo-pure amphiphilic 1,2-amino alcohols by using preparative enantioselective HPLC"
    Chirality, 2022, 34, 295-305.
  6. Jyorthana Rajappa Muralidhar, Koichi Kodama, Takuji Hirose, Yoshihiro Ito and Masuki Kawamoto
    "Photocleavage Behavior of a Polythiophene Derivative Containing a Coumarin Unit"
    Polymer Journal, 2022, 54, 191-198.

2021

  1. Koichi Kodama, Yuki Shimomura and Takuji Hirose
    "Enantiomer separation of nitriles and epoxides by crystallization with chiral organic salts: chirality switching modulated by achiral acids"
    Cryst. Growth Des., 2021, 21, 6552-6557.
  2. Koichi Kodama, Fusato Takase and Takuji Hirose
    "Direct enantioseparation of axially chiral 1,1’-biaryl-2,2’-diols using amidine-based resolving agents"
    RSC Adv., 2021, 11, 18162-18170. (open access)

    (This work was supported by JSPS KAKENHI Grant Number JP20K05458.)

  3. Koichi Kodama, Shohei Yamaguchi, Shigetaka Hayano, Takashi Houkawa, Yoshinori Kitahara, Hiroaki Shitara and Takuji Hirose
    "Characterization and enantiomer separation of indene-derived hexacyclic hydrocarbon and its application as a chiral source"
    Tetrahedron, 2021, 87, 132082.

2020

  1. Yingying Zhao, Xiangyong Wang, Ryo Kaneyama, Koichi Kodama and Takuji Hirose
    "Efficient pyrazole moiety-containing ligands for Cu-catalyzed O-arylation of phenols"
    ChemistrySelect, 2020, 5, 4152-4159.
  2. Koichi Kodama, Meng Yi, Hiroaki Shitara and Takuji Hirose
    "Chirality switching in the enantioseparation of 2-hydroxy-4-phenylbutyric acid: role of solvents in selective crystallization of the diastereomeric salt"
    Tetrahedron Lett., 2020, 61, 151773.

2019

  1. Koichi Kodama, Kozue Kawasaki, Meng Yi, Kaguya Tsukamoto, Hiroaki Shitara and Takuji Hirose
    "Solvent-induced chirality switching in the enantioseparation of halogen-substituted mandelic acids: Structural effects on molecular packing"
    Cryst. Growth Des., 2019, 19, 7153-7159.

    (This work was supported by JSPS KAKENHI Grant Number JP16K17888.)

  2. Md. Mofizur Rahman, Motoki Ueda, Kon Son, Siyoong Seo, Shinji Takeoka, Takuji Hirose and Yoshihiro Ito
    "Tubular network formation by mixing amphiphilic polypeptides with differing hydrophilic blocks"
    Biomacromolecules, 2019, 20, 3908-3914.
  3. Marziyeh Karimiavargani, Seiichi Tada, Noriko Minagawa, Yoshihiro Shimizu, Takuji Hirose, Yoshihiro Ito and Takanori Uzawa
    "Phosphorogenic and spontaneous formation of tris(bipyridine)ruthenium in peptide scaffolds"
    J. Pep. Sci., 2019, 25, e3158.
  4. Koichi Kodama, Ryuta Kawamata and Takuji Hirose
    "Synthesis and evaluation of chiral β-amino acid-based low-molecular-weight organogelators possessing a methyl/trifluoromethyl side chain"
    New J. Chem., 2019, 43, 2882-2887.
    (Selected as a Front Cover)
  5. Takuji Hirose, Zhe Xu, Yuka Kikuchi, Masahito Fukushima, Kengo Kawamura, Yosuke Kaguchi, Koichi Kodama and Mikio Yasutake
    "Polymeric Fibers and Microporous Films by Photo-Crosslinking of Triphenylene-Derived Liquid Crystals"
    J. Polym. Sci. Part A: Polym. Chem., 2019, 57, 605-612.
    (Selected as a Front Cover)

2018

  1. Md. Mofizur Rahman, Motoki Ueda, Takuji Hirose and Yoshihiro Ito
    "Spontaneous Formation of Gating Lipid Domain in Uniform-Size Peptide Vesicles for Controlled Release"
    J. Am. Chem. Soc., 2018, 140, 17956-17961.
    埼玉大学からプレスリリースを行いました。
  2. Yingying Zhao, Xiangyong Wang, Koichi Kodama and Takuji Hirose
    "Copper-catalyzed coupling reactions of aryl halides and phenols by 4,4’-dimethoxy-2,2’-bipyridine and 4,7-dimethoxy-1,10-phenanthroline"
    ChemistrySelect, 2018, 3, 12620-12624.
  3. Tomoe Shimoda, Takeshi Morishima, Koichi Kodama, Takuji Hirose, Dmitry E. Polyansky, Gerald F. Manbeck, James T. Mackerman and Etsuko Fujita
    "Photocatalytic CO2 Reduction by Trigonal Bipyramidal Polypyridyl Cobalt(II) Complexes: Nature of Co(I) and Co(0) Complexes upon their Reactions with CO2, CO or Proton"
    Inorg. Chem., 2018, 57, 5486-5498.
  4. Koichi Kodama, Hayato Kanai, Yuki Shimomura and Takuji Hirose
    "Enantioseparation of sulfoxides and nitriles via inclusion crystallization with chiral organic salts based on L-phenylalanine"
    Eur. J. Org. Chem., 2018, 2018, 1726-1729.
  5. Fathy Hassan, Takafumi Sassa, Takuji Hirose, Yoshihiro Ito and Masuki Kawamoto
    "Light-driven molecular switching of atropisomeric polymers containing azo-binaphthyl groups in their side chains"
    Polymer Journal, 2018, 50, 455-465.
  6. Takuji Hirose, Shujie Qu, Koichi Kodama and Xiangyong Wang
    "Organocatalyst system for disubstituted carbonates from cycloaddition between CO2 and internal epoxides"
    J. CO2 Utilization, 2018, 24, 261-265.
  7. Fathy Hassan, Masuki Kawamoto, Krishnachary Salikolimi, Daisuke Hashizume, Takuji Hirose and Yoshihiro Ito
    "One-pot heterocyclic ring closure of 1,1'-bi-2-naphthol to 7H-dibenzo[c,g]carbazole"
    Tetrahedron Lett., 2018, 59, 99-102.

2017

  1. Mikio Yasutake, Masahiro Takatsudo, Takuya Tamura, Kana Yamada, Tsubasa Kamiya and Takuji Hirose
    "Development of liquid crystal materials having an anthraquinone and bithiophene moieties, and their electrochromic properties"
    Electrochemistry, 2017, 85, 768-774.
  2. Xiangyong Wang, Yingying Zhao, Koichi Kodama and Takuji Hirose
    "Poly(4-vinylphenol)/tetra-n-butylammonium iodide: efficient organocatalytic system for synthesis of cyclic carbonates from CO2 and epoxides"
    J. Appl. Polym. Sci., 2017, 134, 45189.
  3. Koichi Kodama, Jun Nagata, Nobuhiro Kurozumi, Hiroaki Shitara and Takuji Hirose
    "Solvent-induced chirality switching in the enantioseparation of regioisomeric hydroxyphenylpropionic acids via diastereomeric salt formation with (1R,2S)-2-amino-1,2-diphenylethanol"
    Tetrahedron: Asymmetry, 2017, 28, 460-466.
  4. Xiangyong Wang, Lin Wang, Yingying Zhao, Koichi Kodama and Takuji Hirose
    "Efficient and practical organocatalytic system for the synthesis of cyclic carbonates from carbon dioxide and epoxides: 3-hydroxypyridine/tetra-n-butylammonium iodide"
    Tetrahedron, 2017, 73, 1190-1195.
  5. Lin Wang, Naoya Onishi, Kazuhisa Murata, Takuji Hirose, James T. Muckerman, Etsuko Fujita, Yuichiro Himeda
    "Efficient Hydrogen Storage and Production Using a Catalyst with an Imidazoline-Based, Proton-Responsive Ligand"
    ChemSusChem, 2017, 10, 1071-1075.

2016

  1. Koichi Kodama, Rina Morita and Takuji Hirose
    "Formation of ternary inclusion crystal and enantioseparation of alkyl aryl sulfoxides by the salt of urea-modified L-phenylalanine and an achiral amine"
    Cryst. Growth Des., 2016, 16, 5206-5213.
  2. Wei Wang, Liping Zhu, Yoshinori Hirano, Marziyeh Kariminavargani, Seiichi Tada, Guanxin Zhang, Takanori Uzawa, Deqing Zhang, Takuji Hirose, Makoto Taiji and Yoshihiro Ito
    "Fluorogenic enhancement of an in vitro-selected peptide ligand by replacement of a fluorescent group"
    Anal. Chem., 2016, 88, 7991-7997.
  3. Takuji Hirose, Shinsuke Shimizu, Shujie Qu, Hiroaki Shitara, Koichi Kodama and Lin Wang
    " Economical synthesis of cyclic carbonates from carbon dioxide and halohydrins using K2CO3"
    RSC Adv., 2016, 6, 69040-69044.
  4. Koichi Kodama, Naoki Hayashi, Yasuhiko Yoshida and Takuji Hirose
    "Direct enantioseparation of diarylmethylamines with an ortho-hydroxy group via diastereomeric salt formation and their application to the enantioselective addition reaction of diethylzinc"
    Tetrahedron, 2016, 72, 1387-1394.
  5. Lin Wang, Koichi Kodama and Takuji Hirose
    "DBU/benzyl bromide: an efficient catalytic system for the chemical fixation of CO2 into cyclic carbonates under metal- and solvent-free conditions"
    Catal. Sci. Technol., 2016, 6, 3872-3877.
  6. Lin Wang, Guangyou Zhang, Koichi Kodama and Takuji Hirose
    "An efficient metal- and solvent-free organocatalytic system for chemical fixation of CO2 into cyclic carbonates under mild conditions"
    Green Chem., 2016, 18, 1229-1233.
  7. Koichi Kodama, Yuya Morita, Eriko Sekine and Takuji Hirose
    "A systematic study on ternary inclusion crystals consisting of dianilines and three positional isomers of ditoluoyl-L-tartaric acid"
    CrystEngComm, 2016, 18, 123-129.
  8. Li Lin, Guangyou Zhang, Koichi Kodama, Hiroaki Shitara and Takuji Hirose
    "Cationic Polymerization of Vinyl Ethers and p-Methoxystyrene by a Benign Initiating System: Silver Salt/Arylmethyl Halide/Dialkyl Sulfide"
    J. Polym. Sci. Part A: Polym. Chem., 2016, 54, 861-870.

2015

  1. Takuji Hirose, Yutaro Miyazaki, Mizuki Watabe, Sho Akimoto, Tatsuya Tachikawa, Koichi Kodama and Mikio Yasutake
    "Trialkylsilylethynyl-substituted triphenylenes and hexabenzocoronenes: highly soluble liquid crystalline materials and their hole transport abilities"
    Tetrahedron, 2015, 71, 4714-4721.
  2. Li Lin, Guangyou Zhang, Koichi Kodama, Hiroaki Shitara, Mikio Yasutake and Takuji Hirose
    "A Benign Initiating System for Cationic Polymerization of Isobutyl Vinyl Ether: Silver Salt/Aryl(Alkyl) Halide/Lewis Base"
    J. Polym. Sci. Part A: Polym. Chem., 2015, 53, 2050-2058.

2014

  1. Lin Wang, Li Lin, Guangyou Zhang, Koichi Kodama, Mikio Yasutake and Takuji Hirose
    "Synthesis of cyclic carbonates from CO2 and epoxides catalyzed by low loadings of benzyl bromide/DMF at ambient pressure"
    Chem. Commun., 2014, 50, 14813-14816.
  2. Koichi Kodama, Nobuhiro Kurozumi, Hiroaki Shitara and Takuji Hirose
    "Solvent-induced dual chirality switching in the optical resolution of tropic acid via diastereomeric salt formation with (1R,2S)-2-amino-1,2-diphenylethanol"
    Tetrahedron, 2014, 70, 7923-7928.
  3. Koichi Kodama, Hiroaki Shitara and Takuji Hirose
    "Chirality switching in optical resolution of mandelic acid in C1-C4 alcohols: elucidation of solvent effects based on X-ray crystal structures of diastereomeric salts"
    Cryst. Growth Des., 2014, 14, 3549-3556.
  4. Takuji Hirose, Hiroaki Takai, Mizuki Watabe, Hiroyuki Minamikawa, Tatsuya Tachikawa, Koichi Kodama and Mikio Yasutake
    "Effect of alkoxy terminal chain length on mesomorphism of 1,6-disubstituted pyrene-based hexacatenar liquid crystals: Columnar phase control"
    Tetrahedron, 2014, 70, 5100-5108.
  5. Koichi Kodama, Naoki Hayashi, Mikidai Fujita and Takuji Hirose
    "Direct enantioseparation of 1-(2-hydroxyphenyl)ethylamines via diastereomeric salt formation: chiral recognition mechanism based on the crystal structure"
    RSC Adv., 2014, 4, 25609-25615.
  6. Takuji Hirose and Koichi Kodama
    "Recent Advances in Organozinc Reagents" In: Gary A. Molander and Paul Knochel (eds.),
    Comprehensive Organic Synthesis, 2nd Edition, Vol. 1, Oxford: Elsevier; 2014, pp. 204-266.

2013

  1. Hiroaki Shitara, Toshiki Shintani, Koichi Kodama and Takuji Hirose
    "Solvent-induced Reversed Stereoselectivity in Reciprocal Resolutions of Mandelic Acid and erythro-2-Amino-1,2-diphenylethanol"
    J. Org. Chem., 2013, 78, 9309-9316.
    （現代化学2013年11月号で取り上げられました。）
  2. Koichi Kodama, Akinori Kobayashi and Takuji Hirose
    "Synthesis and spectral properties of ruthenium(II) complexes based on 2,2'-bipyridines modified by a perylene chromophore"
    Tetrahedron Lett., 2013, 54, 5514-5517.
  3. 廣瀬　卓司、小玉　康一、設楽　浩明（発明者）
    "エリトロ-2-アミノ-1,2-ジフェニルエタノールの光学分割方法およびマンデル酸の光学分割方法"
    （特許）特願　2013-24783号

2012

  1. Koichi Kodama, Hiroaki Kawamata, Naoya Takahashi and Takuji Hirose
    "Cyanative self-condensation of aromatic aldehydes promoted by VO(OiPr)3-Lewis base as a cooperative catalyst"
    Org. Biomol. Chem., 2012, 10, 9440-9446.
  2. Wan-Hui Wang, Jonathan F. Hull, James T. Muckerman, Etsuko Fujita, Takuji Hirose and Yuichiro Himeda
    "Highly Efficient D2 Generation by Dehydrogenation of Formic Acid in D2O through H+/D+ Exchange on Iridium Catalyst: Application to the Synthesis of Deuterated Compounds by Transfer Deuterogenation"
    Chem. Eur. J., 2012, 18, 9397-9404.
  3. Koichi Kodama, Ayaka Kanno, Eriko Sekine and Takuji Hirose
    "Enantioseparation of 1-arylethanols via a supramolecular chiral host consisting of N-(2-naphthoyl)-L-aspartic acid and an achiral diamine"
    Org. Biomol. Chem., 2012, 10, 1877-1882.

2011

  1. Koichi Kodama, Kazuyuki Sugawara and Takuji Hirose
    "Synthesis of chiral 1,3-diamines derived from cis-2-benzamidocyclohexanecarboxylic acid and their application in the Cu-catalyzed enantioselective Henry reaction"
    Chem. Eur. J., 2011, 17, 13584-13592.
  2. Koichi Kodama, Eriko Sekine and Takuji Hirose
    "Construction of hydrogen-bonded ternary organic crystals derived from L-tartaric acid and their application to enantioseparation of secondary alcohols"
    Chem. Eur. J., 2011, 17, 11527-11534.
  3. Takuji Hirose, Kazuyuki Sugawara and Koichi Kodama
    "Switching of enantioselectivity in the catalytic addition of diethylzinc to aldehydes by regioisomeric chiral 1,3-amino sulfonamide ligands"
    J. Org. Chem., 2011, 76, 5413-5428.　Highlighted in SYNFACTS (Synfacts, 2011, 9, 1004.)
  4. Yuichiro Himeda, Satoru Miyazawa and Takuji Hirose
    "Interconversion between formic acid and H2/CO2 using rhodium and ruthenium catalysts for CO2 fixation and H2 storage"
    ChemSusChem, 2011, 4, 487-493.
  5. Koichi Kodama, Yuria Kimura, Hiroaki Shitara, Mikio Yasutake, Rumiko Sakurai and Takuji Hirose
    "Solvent-induced chirality control in the enantioseparation of 1-phenylethylamine via diastereomeric salt formation"
    Chirality, 2011, 23, 326-332.
  6. Takuji Hirose, Yuki Shibano, Yutaro Miyazaki, Norihito Sogoshi, Seiichiro Nakabayashi and Mikio Yasutake
    "Synthesis and Hole Transport Properties of Highly Soluble Pyrene Based Discotic Liquid Crystals with Trialkylsilylethynyl Groups"
    Mol. Cryst. Liq. Cryst., 2011, 534, 81-92.

2010

  1. Wan-Hui Wang, Takeshi Abe, Xiang-Bo Wang, Koichi Kodama, Takuji Hirose and Guang-You Zhang
    "Self-assembled proline-amino thioureas as efficient organocatalysts for the asymmetric Michael addition of aldehydes to nitroolefins"
    Tetrahedron Asymmetry, 2010, 21, 2925-2933.
  2. Takuji Hirose, Shuhei Shigaki, Makoto Hirose and Atsushi Fushimi
    "Synthesis of new CO2-soluble ruthenium(II) and cobalt(II) polypyridine complexes bearing fluorinated alkyl chains and their application to photoreduction of liq. CO2"
    J. Fluorine Chem., 2010, 131, 915-921.
  3. Takuji Hirose, Takuya Yumoto, Kozue Matsumoto, Satomi Mitsushio, Osamu Kawakami and Mikio Yasutake
    "Liquid-Crystalline Behavior and Structure of Charge-Transfer Complexes of Pyrene Derivatives with Four Linear Alkanoyloxy Substituents"
    Mol. Cryst. Liq. Cryst., 2010, 524, 68-101.
  4. Wan-Hui Wang, Xiang-Bo Wang, Koichi Kodama, Takuji Hirose and Guang-You Zhang
    "Novel chiral ammonium ionic liquids as efficient organocatalysts for asymmetric Michael addition of aldehydes to nitroolefins"
    Tetrahedron, 2010, 66, 4970-4976.
  5. Xiang-Bo Wang, Koichi Kodama, Takuji Hirose, Xiao-Feng Yang and Guang-You Zhang
    "Chirality control in the enantioselective arylation of aromatic aldehydes catalyzed by cis-(1R,2S)-2-benzamidocyclohexanecarboxylic acid derived 1,3-aminoalcohols"
    Tetrahedron Asymmetry, 2010, 21, 75-80.
  6. Xiang-Bo Wang, Koichi Kodama, Takuji Hirose and Guang-You Zhang
    "Chirality control by substituents in the asymmetric addition of Et2Zn to aromatic aldehydes catalyzed by cis-(1R,2S)-2-benzamidocyclohexanecarboxylic acid derived 1,3-aminoalcohols"
    Chinese Journal of Chemistry, 2010, 28, 61-68.

Acknowledgement

  • ここに示す研究成果の多くは科研費の助成を受けて行われました。ここに御礼申し上げます。
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