清水 大貴 (Daiki Shimizu, Ph.D.)

京都大学大学院工学研究科 合成・生物化学専攻
合成化学講座 物理有機化学分野(松田研究室)助教

工学研究科次世代学際院 次世代研究者

京都市西京区京都大学桂 A4棟325号室
e-mail: dshimizu(at)sbchem.kyoto-u.ac.jp
Tel: 075-383-2746
Fax: 075-383-2741

Curriculum Vitae (PDF)




2010-03 愛知県立刈谷高等学校 卒業
2014-03 京都大学理学部 卒業
2016-03 京都大学大学院理学研究科 化学専攻 修士課程 修了
2019-03 京都大学大学院理学研究科 化学専攻 博士後期課程 修了(大須賀篤弘 教授)
2019-03 博士(理学)
学位論文 "Chemistry of Stable Open-shell Porphyrinoids"


2016-04/2019-03 日本学術振興会特別研究員(DC1)
2017-08/2017-11 米国Northwestern大学 Visiting Scholar (Michael R. Wasielewski Group)
2019-04/現在 京都大学大学院工学研究科 合成・生物化学専攻 助教


2016-10 第 7 回大津会議アワードフェロー(No. 107)
2017-03 学生講演賞@日本化学会第 97 春季年会
2017-08 ポスター賞@第 48 回構造有機若手の会夏の学校
2018-09 RSC Advances賞@第 29 回基礎有機化学討論会

Chemical Reviews Poster Prize@The 10th Singapore
International Chemistry Conference (SICC-10)

2020-02 第 36 回 井上研究奨励賞
2023-12 第 36 回 有機合成化学協会 三菱ケミカル 研究企画賞


  • 51. H. Hamamoto, D. Shimizu, K. Matsuda
    peri-Benzo-Diindenotetracenyl: Helically π-Extended Allyl Radical with Robust Stability”
    Manuscript submitted. [DOI: ///]
  • 50. D. Shimizu, H. Sotome, H. Miyasaka, K. Matsuda
    “Optically Distinguishable Electronic Spin-isomers of a Stable Organic Diradical”
    ACS Cent. Sci. 2024, 10, 890-898. [DOI: 10.1021/acscentsci.4c00284] (Open access)
    Press Release [KyotoU] [OsakaU]
  • 49. T. Shinozuka, D. Shimizu, K. Matsuda
    “Theoretical investigation on the effect of radical substituents on the open-shell character of polycyclic aromatic hydrocarbon”
    New J. Chem. 2024, accepted. [DOI: 10.1039/D4NJ00555D] (Open access)
  • 48. M. Hisada, D. Shimizu, K. Matsuda
    “Synthesis and properties of doubly diphenylene-fused benzopyrrolo[1,4]diazocine with a [7-8-7] successive ring-fused structure”
    Chem. Lett. 2024, 53, upae021. [DOI: 10.1093/chemle/upae021]
  • 47. K. Wang, S. Ito, S. Ren, D. Shimizu, N. Fukui, R. Kishi, Q. Liu, A. Osuka, J. Song, H. Shinokubo
    “A Triply-Linked Porphyrin−Norcorrole Hybrid with Singlet Diradical Character”
    Angew. Chem. Int. Ed. 2024, 63, e202401233. [DOI: 10.1002/anie.202401233]
  • 46. H. Hamamoto, D. Shimizu, K. Matsuda
    “Verdazyl–Nitroxide Diradical with S = 1 Ground State: Observation of Long-Range Ordering and Haldane Gap in a Highly Isotropic S = 1 Antiferromagnetic Heisenberg Chain”
    J. Phys. Chem. C 2023, 127, 21822-21828. [DOI: 10.1021/acs.jpcc.3c05584]
  • 45. Y. Takeo, J. Hirano, D. Shimizu, N. Fukui, H. Shinokubo
    “Effect of internal oxygen substituents on the properties of bowl-shaped aromatic hydrocarbons”
    Org. Chem. Front. 2023, 10, 5895-5901. [DOI: 10.1039/D3QO01661G]
  • 44. M. Kato, J. Kim, J. Oh, D. Shimizu, N. Fukui, H. Shinokubo
    “Near-Infrared-Responsive Hydrocarbons Designed by π-Extension of Indeno[1,2,3,4-pgra]perylene at the 1,2,12-Positions”
    Chem. Eur. J. 2023, 29, e202300249. [DOI: 10.1002/chem.202300249]
  • 43. W. Deng, Y. Liu, D. Shimizu, T. Tanaka, A. Nakai, Y. Rao, L. Xu, M. Zhou, A. Osuka, J. Song
    “Facile Formation of Stable Neutral Radicals and Cations from [22]Smaragdyrin BF2 Complexes”
    Chem. Eur. J. 2023, 29, e202203484. [DOI: 10.1002/chem.202203484]
  • 42. M. Hisada, D. Shimizu, K. Matsuda
    “π-Expansion of 2,3,6,7-Tetraazanaphthalene with Two Embedded Heptagons: Highly Twisted Structure and Lone-Pair/π* Interaction in the Crystal”
    Org. Lett. 2022, 24, 3707-3711. [DOI: 10.1021/acs.orglett.2c01345]
  • 41. M. Hisada, D. Shimizu, K. Matsuda
    “Heptagon-Embedded π-Expanded Thieno- and N-Methylpyrrolo-Pyridazines with Substantial Out-of-Plane Dipole Moment”
    J. Org. Chem. 2022, 87, 9034-9043. [DOI: 10.1021/acs.joc.2c00709]
    (Preprint: ChemRxiv, 10.26434/chemrxiv-2022-cnpr2).
  • 40. R. Yasui, D. Shimizu, K. Matsuda
    “Large Enhancement of Single Molecular Conductance of Molecular Wire through a Radical Substituent”
    Chem. Eur. J. 2022, 28, e202104242. [DOI: 10.1002/chem.202104242]
  • 39. Y. Nakakuki, T. Hirose, H. Sotome, M. Gao, D. Shimizu, R. Li, J.-y. Hasegawa, H. Miyasaka, K. Matsuda
    “Doubly linked chiral phenanthrene oligomers for homogeneously π-extended helicenes with large effective conjugation length”
    Nat. Commun. 2022, 13, 1475. [DOI: 10.1038/s41467-022-29108-8]
  • 38. H. He, Z. Ye, D. Shimizu, I. Sumra, Y. Zhang, Z. Liang, Y. Zeng, L. Xu, A. Osuka, Z. Ke, H.-W. Jiang
    “Formation of Stable Ni(III) N-Confused Porphyrins Aided by 3-Ethoxy Group”
    Chem. Eur. J. 2022, 28, e202103272. [DOI: 10.1002/chem.202103272]
  • 37. T. Shinozuka, S. Nishizawa, D. Shimizu, K. Matsuda
    “Evaluation of electron transport capability of armchair graphene nanoribbons (AGNRs) by calculating exchange interaction between terminally attached radicals”
    Chem. Phys. Lett. 2021, 780, 138923. [DOI: 10.1016/j.cplett.2021.138923]
  • 36. H. Kubo, T. Hirose, D. Shimizu, K. Matsuda
    “Donor-Acceptor Type [5]Helicene Derivative with Strong Circularly Polarized Luminescence”
    Chem. Lett. 2021, 50, 804-807. [DOI: 10.1246/cl.200913]
  • 35. H. Kubo, D. Shimizu, T. Hirose, K. Matsuda
    “Circularly Polarized Luminescence Designed from Molecular Orbit-als: A Figure-Eight-Shaped [5]Helicene Dimer with D2 Symmetry”
    Org. Lett. 2020, 22, 9276-9281. [DOI: 10.1021/acs.orglett.0c03506]
  • 34.Y. J. Bae, D. Shimizu, J. D. Schultz, G. Kang, J. Zhou, G. C. Schatz, A. Osuka, M. R. Wasielewski
    “Balancing Charge Transfer and Frenkel Exciton Coupling Leads to Excimer Formation in Molecular Dimers: Implications for Singlet Fission”
    J. Phys. Chem. A 2020, 124, 8478-8487. [DOI: 10.1021/acs.jpca.0c07646]
  • 33. T. Iizuka, D. Shimizu, K. Matsuda
    “STM apparent height measurements of molecular wires with different physical length attached on 2-D phase separated templates for evaluation of single molecular conductance”
    RSC Adv. 2020, 10, 22054-22057. [DOI: 10.1039/D0RA04484A]
  • 32. S. Ooi, B. Adinarayana, D. Shimizu, T. Tanaka, and A. Osuka
    “Stable meso-meso Linked 2NH-Corrole Radical Dimers as a Key Intermediate to Corrole Tape”
    Angew. Chem. Int. Ed. 2020, 59, 9423-9427. [DOI: 10.1002/anie.202002976]
  • 31. M. Izawa, T. Suito, S. Ishida, D. Shimizu, T. Tanaka, T. Mori, A. Osuka
    “Figure-eight Octaphyrin Bis-Ge(IV) Complexes: Synthesis, Structures, Aromaticity, and Chiroptical Properties”
    Chem. Asian J. 2020, 15, 1440-1448. [DOI: 10.1002/asia.202000159]
  • 30. G. Lavarda, D. Shimizu, T. Torres, A. Osuka
    meso-(2-Pyridyl)-boron(III)-subporphyrin: Perimeter Iridium(III) Coordination”
    Angew. Chem. Int. Ed. 2020, 59, 3127-3130. [DOI: 10.1002/anie.201914853]
  • 29. B. Adinarayana, K. Kato, D. Shimizu, K. Furukawa, T. Tanaka, A. Osuka
    “Cyclophane-type Chlorin Dimers from Dynamic Covalent Chemistry of 2,18-Porphyrinyl Dicyanomethyl Diradicals”
    Angew. Chem. Int. Ed. 2020, 4320-4323. [DOI: 10.1002/anie.201914480]
  • 28. T. Yamamoto, K. Kato, D. Shimizu, T. Tanaka, A. Osuka
    “Phenylene-bridged Porphyrin meso-Oxy Radical Dimers”
    Chem. Asian J. 2019, 14, 4031-4034. [DOI: 10.1002/asia.201901033]
  • 27. C. Schierl, W. Alex, L. M. Mateo, B. Ballesteros, D. Shimizu, A. Osuka, T. Torres, D. M. Guldi, G. Bottari
    “Quadrupolar Cyclopenta[hi]aceanthrylene‐based Electron Donor‐Acceptor‐Donor Conjugates: Charge Transfer versus Charge Separation”
    Angew. Chem. Int. Ed. 2019, 58, 14644-14652. [DOI: 10.1002/anie.201906206]
  • 26. B. Adinarayana, D. Shimizu, K. Furukawa, A. Osuka
    “Stable radical versus reversible σ-bond formation of (porphyrinyl)dicyanomethyl radicals”
    Chem. Sci. 2019, 10, 6007-6012. [DOI: 10.1039/C9SC01631G]
  • 25. D. Shimizu, Y. Ide, T. Ikeue, A. Osuka
    “Coordination-Induced Spin-State Switching of an Aminyl-Radical-Bridged Nickel(II) Porphyrin Dimer between Doublet and Sextet States”
    Angew. Chem. Int. Ed. 2019, 58, 5023-5027. [DOI: 10.1002/anie.201900792]
  • 24. K. Fujimoto, D. Shimizu, T. Mori, Y. Li, M. Zhou, J. Song, A. Osuka
    “Selective Formation of Helical Tetrapyrrin-fused Porphyrins by Oxidation of β-to-β Linked meso-Aminoporphyrin Dimers”
    Chem. Eur. J. 2019, 25, 1711-1715. [DOI: 10.1002/chem.201805659]
  • 23. B. Adinarayana, D. Shimizu, A. Osuka
    “Stable (BIII-Subporphyrin-5-yl)dicyanomethyl Radicals”
    Chem. Eur. J. 2019, 25, 1706-1710. [DOI: 10.1002/chem.201805601]
  • 22. K. Fujimoto, D. Shimizu, A. Osuka
    “Porphyrin-Stabilized Nitrenium Dication”
    Chem. Eur. J. 2019, 25, 521-525. [DOI: 10.1002/chem.201805491]
  • 21. S. Ooi, T. Tanaka, T. Ikeue, K. Yamasumi, K Ueta, D Shimizu, M. Ishida, H. Furuta, A. Osuka
    “Bis-copper(II) Complex of Triply-linked Corrole Dimer and Its Dication”
    Chem. Asian J. 2019, 14, 1771-1776. [DOI: 10.1002/asia.201801467]
  • 20. S. Ooi, D. Shimizu, K. Furukawa, T. Tanaka, A. Osuka
    “Stable Face‐to‐Face Singlet Diradicaloids: Triply Linked Corrole Dimer Gallium(III) Complexes with Two μ‐Hydroxo‐Bridges”
    Angew. Chem. Int. Ed. 2018, 57, 14916-14920. [DOI: 10.1002/anie.201810200]
  • 19. Y. Bekki, D. Shimizu, K. Fujimoto, A. Osuka
    meso-Functionalizations of BIII Subporphyrin with BIII meso-Lithiosubporphyrin”
    Chem. Eur. J. 2018, 24, 12708-12715. [DOI: 10.1002/chem.201802339]
  • 18. D. Shimizu, K. Fujimoto, A. Osuka
    “Stable Diporphyrinyl-Aminyl Radical and Nitrenium Ion”
    Angew. Chem. Int. Ed. 2018, 57, 12708-12715. [DOI: 10.1002/anie.201805385]
  • 17. K. Kise, Y. Hong, N. Fukui, D. Shimizu, D. Kim, A. Osuka
    “Diarylamine-fused Subporphyrins: Proof of Twisted Intramolecular Charge Transfer (TICT) Mechanism”
    Chem. Eur. J. 2018, 24, 8306-8310. [DOI: 10.1002/chem.201801576]
  • 16. K. Kise, K. Yoshida, R. Kotani, D. Shimizu, A. Osuka
    “BIII 5-Arylsubporphyrins and BIII subporphine”
    Chem. Eur. J. 2018, 24, 19136-19140. [DOI: 10.1002/chem.201801491]
  • 15. S. Ishida, J. Kim, D. Shimizu, D. Kim, A. Osuka
    “Synthesis of bis-Silicon Complexes of [38]-, [37]-, and [36] Octaphyrins: Aromaticity Switch and Stable Radical Cation”
    Angew. Chem. Int. Ed. 2018, 57, 5876-5880. [DOI: 10.1002/anie.201801986]
  • 14. D. Shimizu, A. Osuka
    “A Benzene-1,3,5-Triaminyl Radical Fused with Zn(II)-Porphyrins: Remarkable Stability and High Spin Quartet Ground State”
    Angew. Chem. Int. Ed. 2018, 57, 3733-3736. [DOI: 10.1002/anie.201801080]
  • 13. D. Shimizu, K Furukawa, A. Osuka
    “Stable Subporphyrin meso-Aminyl Radicals without Resonance Stabilization by Neighboring Heteroatom”
    Angew. Chem. Int. Ed. 2017, 56, 7435-7439. [DOI: 10.1002/anie.201703097]
  • 12. K. Naoda, D. Shimizu, J. O. Kim, K. Furukawa, D. Kim, A. Osuka
    “Thienylquinonoidal Porphyrins and Hexaphyrins with Singlet Diradical Ground States”
    Chem. Eur. J. 2017, 23, 8969-8879. [DOI: 10.1002/chem.201701355]
  • 11. C. Stähler, D. Shimizu, K. Yoshida, K. Furukawa, R. Herges, A. Osuka
    “Stable NiII Porphyrin meso-Oxy Radical with a Quartet Ground State”
    Chem. Eur. J. 2017, 23, 7217-7200. [DOI: 10.1002/chem.201701354]
  • 10. D. Shimizu, S.-K. Lee, D. Kim, A. Osuka
    meso-Nitro- and meso-Aminosubporphyrinatoboron(III)s and meso-to-meso-Azosubporphyrinatoboron(III)s”
    Chem. Asian J. 2016, 11, 2946-2952. [DOI: 10.1002/asia.201601019]
  • 9. N. Fukui, W. Cha, D. Shimizu, J. Oh, K. Furukawa, H. Yorimitsu, D. Kim, A. Osuka
    “Highly planar diarylamine-fused porphyrins and their remarkably stable radical cations”
    Chem. Sci. 2017, 8, 189-199. [DOI: 10.1039/C6SC02721K]
  • 8. S.-K. Lee, J. O. Kim, D. Shimizu, A. Osuka, D. Kim
    “Effect of bulky meso-substituents on photoinduced twisted intramolecular charge transfer processes in meso-diarylamino subporphyrins”
    J. Porphyrins Phthalocyanines 2016, 20, 663-669. [DOI: 10.1142/S1088424616500723]
  • 7. G. Copley, D. Shimizu, J. Oh, J. Sung, K. Furukawa, D. Kim, A Osuka
    meso-to-meso Sulfide- and Disulf­ide-Bridged Subporphyrin Dimers”
    Eur. J. Org. Chem. 2016, 1977-1981. [DOI: 10.1002/ejoc.201600285]
  • 6. N. Fukui, S.-K. Lee, K. Kato, D. Shimizu, T. Tanaka, S. Lee, H. Yorimitsu, D. Kim, A. Osuka
    “Regioselective phenylene-fusion reactions of Ni(II)-porphyrins controlled by an electron-withdrawing meso-substituent”
    Chem. Sci. 2016, 7, 4059-4066. [DOI: 10.1039/C5SC04748J]
  • 5. G. Copley, J. Oh, K. Yoshida, D. Shimizu, D. Kim, A. Osuka
    “Intramolecular electron transfer reactions in meso-(4-nitrophenyl)-substituted subporphyrins”
    Chem. Commun. 2016, 52, 1424-1427. [DOI: 10.1039/c5cc09005a]
  • 4. D. Shimizu, J. Oh, K. Furukawa, D. Kim, A. Osuka
    “Triarylporphyrin meso-Oxy Radicals: Remarkable Chemical Stabilities and Oxidation to Oxophlorin π-Cations”
    J. Am. Chem. Soc. 2015, 137, 15584-15594. [DOI: 10.1021/jacs.5b11223]
  • 3. D. Shimizu, J. Oh, K. Furukawa, D. Kim, A. Osuka
    “meso-Hydroxysubporphyrins: a Cyclic Trimeric Assembly and a Stable meso-Oxy Radical”
    Angew. Chem. Int. Ed. 2015, 54, 6613-6617. [DOI: 10.1002/anie.201501592]
  • 2. D. Shimizu, H. Mori, M. Kitano, W.-Y. Cha, J. Oh, T. Tanaka, D. Kim, A. Osuka
    “Nucleophilic Aromatic Substitution Reactions of meso-Bromosubporphyrin: Synthesis of a Thiopyrane-Fused Subporphyrin””
    Chem. Eur. J. 2014, 20, 16194-16202. [DOI: 10.1002/chem.201405110]
  • 1. M. Kitano, D. Shimizu, T. Tanaka, H. Yorimitsu, A. Osuka
    “Synthesis of meso-heteroatom-substituted subporphyrins”
    J. Porphyrins Phthalocyanines 2014, 18, 659-665. [DOI: 10.1142/s1088424614500394]


  • 1. D. Shimizu and A. Osuka
    “Porphyrinoids as a platform of stable radicals”
    Chem. Sci. 2018, 9, 1408−1423. [DOI: 10.1039/C7SC05210C]


  • 7. 清水 大貴
    2023 年 光化学若手の会
    津名ハイツ, 淡路島, 2023-06-09/11
  • 6. 清水 大貴
    第 7 回有機若手ワークショップ
    京都大学吉田キャンパス, 2022-11-29
  • 5. Daiki Shimizu
    “Spin-state dependent optical behavior of a stable Blatter radical dimer with through-space interaction”
    The 9th International Kyoto Symposium on Organic Chemistry
    (pre-Tateshina Conference/The 13th JGP Chem&ChemEn Workshop)
    京都大学桂キャンパス, 2022-11-09
  • 4. 清水 大貴
    構造有機 Mirai セミナー
    札幌, 2022-06-24/25
  • 3. 清水 大貴
    GTR Chemistry Workshop 2021
    名古屋大学卓越大学院プログラム トランスフォーマティブ化学生命融合研究大学院プログラム
    オンライン, 2021-11-29
  • 2. 清水 大貴
    オンライン, 2021-11-26
  • 1. 清水 大貴
    2018 年度 高分子・ハイブリッド材料研究センター(PHyM)若手フォーラム
    仙台, 2018-11-19