New Main Group Element Chemistry and Materials Science Based on Heavy Aryl Anions

• Project/Area Number: 19H05635
• Research Category: Grant-in-Aid for Scientific Research (S)
• Allocation Type: Single-year Grants
• Review Section: Broad Section E
• Research Institution: Kyoto University
• Principal Investigator: 時任 宣博 京都大学, 化学研究所, 特任教授 (90197864)
• Co-Investigator(Kenkyū-buntansha): 水畑 吉行 京都大学, 化学研究所, 准教授 (30437264) ; 行本 万里子 京都大学, 化学研究所, 助教 (70822964)
• Project Period (FY): 2019-06-26 – 2024-03-31
• Project Status: Completed (Fiscal Year 2023)
• Budget Amount: ¥201,110,000 (Direct Cost: ¥154,700,000、Indirect Cost: ¥46,410,000); Fiscal Year 2023: ¥18,590,000 (Direct Cost: ¥14,300,000、Indirect Cost: ¥4,290,000); Fiscal Year 2022: ¥18,590,000 (Direct Cost: ¥14,300,000、Indirect Cost: ¥4,290,000); Fiscal Year 2021: ¥18,590,000 (Direct Cost: ¥14,300,000、Indirect Cost: ¥4,290,000); Fiscal Year 2020: ¥81,380,000 (Direct Cost: ¥62,600,000、Indirect Cost: ¥18,780,000); Fiscal Year 2019: ¥63,960,000 (Direct Cost: ¥49,200,000、Indirect Cost: ¥14,760,000)
• Keywords: アリールアニオン / 芳香族化合物 / 高周期元素 / 典型元素 / 拡張パイ電子系 / 有機元素化学 / 高周期14族元素 / フェニルアニオン / 共役系化合物

Outline of Research at the Start

本研究では、代表者らがごく最近初めてその合成・単離に成功したフェニルアニオンの高周期14族元素類縁体における安定化の概念を広く拡張し、系統的に誘導体を構築し、その基本的性質、反応性を解明する。これらの含高周期14族元素フェニルアニオン類は、かさ高い置換基を持たなくとも分子間の電荷反発により自己多量化を防ぐことを発見している。それらを踏まえた上で、炭素類縁体との電子状態の違いを引き出す分子設計を行い、重い元素を含む新規共役系分子、究極的な目標としてグラフェンの骨格炭素を高周期14族元素に置き換えた「重いグラフェン」の構築を目指す。

Outline of Annual Research Achievements

フェニルアニオンのアニオン炭素を高周期14族元素に置き換えた「重いフェニルアニオン」に関して、既に合成・単離を報告しているゲルマニウムおよびスズ類縁体に加え、ケイ素類縁体であるシラベンゼニルアニオンの合成に関して検討を進めた。ゲルマニウム・スズ類縁体合成と同様にTbt基置換中性シラベンゼンの還元を行うと、従前の系と異なり置換基の脱離が進行せず、Tbt基のオルトベンジルプロトンがケイ素中心に引き抜かれることを明らかにしている。中心元素による反応性の違いを理論計算を用いて詳細に検討し、中間体ジアニオンにおける中心元素の混成状態およびベンジルプロトンとの相互作用の違いが重要であることを示した。
また、近畿大学　松尾司教授の協力のもと、オルトベンジルプロトンを持たない置換基であるEindを活用し、Eind置換シラベンゼンの合成およびその還元反応を検討した。その結果、期待通りに置換基の脱離反応が進行した一方、発生したシラベンゼニルアニオンは極めて高反応性であり、その多量体を与えることがわかった。金属錯化等の配位安定化を活用した単量体の発生確認を推し進めている。
加えて、昨年度までに見いだしているゲルマベンゼニルアニオンを用いた単原子ゲルマニウム輸送反応の条件検討を行い、中間体であるゲルマベンゼニルゲルミレンのルイス塩基錯体の利用およびルイス塩基の添加により、目的とする反応が高効率で進行することを見いだした。本反応を活用することで、従来はハロゲン化化合物の還元的手法により合成されてきた種々のクラスター群を非還元的かつ穏やかな条件で構築することが可能となった。

Research Progress Status

令和5年度が最終年度であるため、記入しない。

Strategy for Future Research Activity

令和5年度が最終年度であるため、記入しない。

Assessment Rating

Interim Assessment Comments (Rating)

A-: In light of the aim of introducing the research area into the research categories, the expected progress in research has been made on the whole though a part of it has been delayed.

Research Products

• [Journal Article] Synthesis of 1‐Adamantylaminogermylene and Its Chalcogenation Reactions (2024)
  • Author(s): Yukimoto Mariko、Kanda Kazuaki、Aoki Takamasa、Mizuhata Yoshiyuki、Tokitoh Norihiro
  • Journal Title: European Journal of Inorganic Chemistry Volume: 27 Issue: 7
  • DOI: 10.1002/ejic.202300663
  • Peer Reviewed
• [Journal Article] Potassium 2-germanaphthalenide: an isolable polycyclic system of germanium-incorporated anionic benzenoid (2024)
  • Author(s): Tsuji Shingo、Tokitoh Norihiro、Yamada Hiroko、Mizuhata Yoshiyuki
  • Journal Title: Inorganic Chemistry Frontiers Volume: 11 Issue: 2 Pages: 400-408
  • DOI: 10.1039/d3qi02183a
  • Peer Reviewed
• [Journal Article] Recent progress in the chemistry of heavy aromatics (2023)
  • Author(s): Fujimori Shiori、Mizuhata Yoshiyuki、Tokitoh Norihiro
  • Journal Title: Proceedings of the Japan Academy, Series B Volume: 99 Issue: 10 Pages: 480-512
  • DOI: 10.2183/pjab.99.027
  • ISSN: 0386-2208, 1349-2896
  • Year and Date: 2023-12-11
  • Peer Reviewed / Open Access
• [Journal Article] The Reduction of Metallabenzenes: Different Scenarios Highly Dependent on the Central Group 14 Elements, Si vs. Ge (2023)
  • Author(s): Tsuji Shingo、Tokitoh Norihiro、Yamada Hiroko、Mizuhata Yoshiyuki
  • Journal Title: Chemistry - An Asian Journal Volume: 19 Issue: 2
  • DOI: 10.1002/asia.202300945
  • Peer Reviewed
• [Journal Article] Small molecule activation based on novel heavier group 13/15 interelement compounds, λ3,λ3-phosphanylalumanes (2023)
  • Author(s): Yanagisawa Tatsuya、Mizuhata Yoshiyuki、Tokitoh Norihiro
  • Journal Title: Bulletin of the Chemical Society of Japan Volume: 97 Issue: 1
  • DOI: 10.1093/bulcsj/bcsj.20230186
  • Peer Reviewed / Open Access
• [Journal Article] Synthesis and characterization of novel hydrodigermenide and digermyne radical anion (2023)
  • Author(s): Mizuhata Yoshiyuki、Ijichi Wataru、Nishino Ryohei、Kato Tatsuhisa、Kayahara Eiichi、Yamago Shigeru、Tokitoh Norihiro
  • Journal Title: Polyhedron Volume: 244 Pages: 116614-116614
  • DOI: 10.1016/j.poly.2023.116614
  • Peer Reviewed
• [Journal Article] Unusual nuclear exchange within a germanium-containing aromatic ring that results in germanium atom transfer (2023)
  • Author(s): Nishino Ryohei、Tokitoh Norihiro、Sasayama Ryuto、Waterman Rory、Mizuhata Yoshiyuki
  • Journal Title: Nature Communications Volume: 14 Issue: 1 Pages: 4519-4519
  • DOI: 10.1038/s41467-023-40188-y
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Solid‐state Chromism of Zwitterionic Triarylmethylium Salts (2023)
  • Author(s): Iwai Kento、Mizuhata Yoshiyuki、Nakamura Tomoya、Goto Masato、Wakamiya Atsushi、Shimakawa Yuichi、Tokitoh Norihiro
  • Journal Title: European Journal of Inorganic Chemistry Volume: 26 Issue: 31
  • DOI: 10.1002/ejic.202300337
  • Peer Reviewed
• [Journal Article] Synthesis and characterization of a polystyrene-type polymer bearing a cyclic perfluoroalkylene group (2023)
  • Author(s): Hisa Tatsuro、Kanno Yasunori、Shirai Tomohiro、Oshiki Toshiyuki、Mizuhata Yoshiyuki、Tokitoh Norihiro、Fukumoto Hiroki、Agou Tomohiro
  • Journal Title: Polymer Volume: 265 Pages: 125588-125588
  • DOI: 10.1016/j.polymer.2022.125588
  • Peer Reviewed
• [Journal Article] Control over Ligand-Exchange Positions of Thiolate-Protected Gold Nanoclusters Using Steric Repulsion of Protecting Ligands (2022)
  • Author(s): Suzuki Wataru、Takahata Ryo、Chiga Yuki、Kikkawa Soichi、Yamazoe Seiji、Mizuhata Yoshiyuki、Tokitoh Norihiro、Teranishi Toshiharu
  • Journal Title: Journal of the American Chemical Society Volume: 144 Issue: 27 Pages: 12310-12320
  • DOI: 10.1021/jacs.2c03670
  • Peer Reviewed
• [Journal Article] Boron complexes of π-extended nitroxide ligands exhibiting three-state redox processes and near-infrared-II (NIR-II) absorption properties (2022)
  • Author(s): Nakamura Marika、Hyakutake Risa、Morisako Shogo、Sasamori Takahiro、Mizuhata Yoshiyuki、Tokitoh Norihiro、Nakashima Kouichi、Fukumoto Hiroki、Agou Tomohiro
  • Journal Title: Dalton Transactions Volume: 51 Issue: 36 Pages: 13675-13680
  • DOI: 10.1039/d2dt02545k
  • Peer Reviewed
• [Journal Article] Synthesis of a Kinetically Stabilized 2,2-Dihydrosilene (2022)
  • Author(s): Garcia Julius Adrie、Yasui Yuji、Yukimoto Mariko、Mizuhata Yoshiyuki、Tokitoh Norihiro
  • Journal Title: Chemistry Letters Volume: 51 Issue: 9 Pages: 898-901
  • DOI: 10.1246/cl.220275
  • Peer Reviewed
• [Journal Article] Synthesis of perfluoroalkylene-vinylene-arylene copolymers via the Mizoroki-Heck co-polymerization of 1,4-divinylperfluorobutane and 1,6-divinylperfluorohexane with dihalogenated arylene monomers (2022)
  • Author(s): Tsukada Hiroto、Hisa Tatsuro、Shirai Tomohiro、Oshiki Toshiyuki、Mizuhata Yoshiyuki、Tokitoh Norihiro、Fukumoto Hiroki、Agou Tomohiro
  • Journal Title: Journal of Fluorine Chemistry Volume: 261-262 Pages: 110033-110033
  • DOI: 10.1016/j.jfluchem.2022.110033
  • Peer Reviewed
• [Journal Article] Synthesis of Twisted [ <i>n</i> ]Cycloparaphenylene by Alkene Insertion (2022)
  • Author(s): Terabayashi Tomoaki、Kayahara Eiichi、Zhang Yichen、Mizuhata Yoshiyuki、Tokitoh Norihiro、Nishinaga Tohru、Kato Tatsuhisa、Yamago Shigeru
  • Journal Title: Angewandte Chemie International Edition Volume: 62 Issue: 2
  • DOI: 10.1002/anie.202214960
  • Peer Reviewed
• [Journal Article] Amidinate bromogermylene resulting from carbodiimide insertion into Ar?GeBr bond (2022)
  • Author(s): Sasamori Takahiro、Sugahara Tomohiro、Tokitoh Norihiro
  • Journal Title: Mendeleev Communications Volume: 32 Issue: 1 Pages: 63-65
  • DOI: 10.1016/j.mencom.2022.01.020
  • Peer Reviewed / Open Access
• [Journal Article] Reaction of an Overcrowded 1,2-Diaryl-1,2-dibromodisilene with 1-Vinylcyclohepta-1,3,5-triene: Isolation of a 2-Vinylsilacyclopropane Derivative and Its Thermal Conversion to a Silacyclopent-3-ene Derivative (2022)
  • Author(s): Mizuhata Yoshiyuki、Tokitoh Norihiro、Oshiro Taku
  • Journal Title: HETEROCYCLES Volume: 104 Issue: 2 Pages: 389-389
  • DOI: 10.3987/com-21-14585
  • Peer Reviewed
• [Journal Article] Template Synthesis of Novel Norcorrole Complexes with a Phenyl‐substituted Phosphorus Center (2022)
  • Author(s): Jun‐i Yuta、Mizuhata Yoshiyuki、Tokitoh Norihiro
  • Journal Title: European Journal of Organic Chemistry Volume: 2022 Issue: 5
  • DOI: 10.1002/ejoc.202101312
  • Peer Reviewed
• [Journal Article] Convergent Synthesis of <i>E</i> ‐Disilene by the Reduction of Diastereomerically Separable 1,2‐Dichlorodisilanes (2022)
  • Author(s): Jun‐i Yuta、Mizuhata Yoshiyuki、Tokitoh Norihiro
  • Journal Title: European Journal of Inorganic Chemistry Volume: 2022 Issue: 5
  • DOI: 10.1002/ejic.202100962
  • Peer Reviewed
• [Journal Article] 2-Germaazulene: Synthesis and Properties of 2-Heteraazulene Containing a Germanium Atom as a Skeletal Element (2022)
  • Author(s): Oshiro Taku、Mizuhata Yoshiyuki、Tokitoh Norihiro
  • Journal Title: Chemistry Letters Volume: 51 Issue: 3 Pages: 312-316
  • DOI: 10.1246/cl.210773
  • Peer Reviewed
• [Journal Article] Glucose as a Protein-Condensing Cellular Solute (2022)
  • Author(s): Noda, N., Jung, Y., Ado, G., Mizuhata, Y., Higuchi, M., Ogawa, T., Ishidate, F., Sato, S., Kurata, H., Tokitoh, N., Uesugi, M.
  • Journal Title: ACS Chem. Biol. Volume: 17 Issue: 3 Pages: 567-575
  • DOI: 10.1021/acschembio.1c00849
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] A Novel Reactivity of Phosphanylalumane (>P-A<): Reversible Addition of a Saturated Interelement Bond to Olefins (2021)
  • Author(s): Yanagisawa Tatsuya、Mizuhata Yoshiyuki、Tokitoh Norihiro
  • Journal Title: Chemistry - A European Journal Volume: 27 Issue: 44 Pages: 11273-11278
  • DOI: 10.1002/chem.202101649
  • Peer Reviewed
• [Journal Article] Fused-Nonacyclic Multi-Resonance Delayed Fluorescence Emitter Based on Ladder-Thiaborin Exhibiting Narrowband Sky-Blue Emission with Accelerated Reverse Intersystem Crossing (2021)
  • Author(s): Ｍasakazu Ｎagata, Ｈyukgi Ｍin, Ｅrika Watanabe, Hiroki Fukumoto, Yoshiyuki Mizuhata, Norihiro Tokitoh, Tomohiro Agou, Takuma Yasuda
  • Journal Title: Angewandte Chemie International Edition Volume: 60 Issue: 37 Pages: 20280-20285
  • DOI: 10.1002/anie.202108283
  • Peer Reviewed
• [Journal Article] A unique 1,4-silyl group migration from carbon to carbon: Formation of benzylic silane in the reaction of sterically hindered benzylic telluride with alkyllithium (2021)
  • Author(s): Garcia Julius Adrie、Yukimoto Mariko、Mizuhata Yoshiyuki、Tokitoh Norihiro
  • Journal Title: Journal of Organometallic Chemistry Volume: 956 Pages: 122119-122119
  • DOI: 10.1016/j.jorganchem.2021.122119
  • Peer Reviewed
• [Journal Article] Synthesis of Carbazole-Fused Azaborines via a Pd-Catalyzed C-H Activation-Cyclization Reaction (2021)
  • Author(s): Nagata Masakazu、Oshiro Taku、Mizuhata Yoshiyuki、Tokitoh Norihiro、Hosoya Takaaki、Yamada Shigeyuki、Konno Tsutomu、Fukumoto Hiroki、Kubota Toshio、Agou Tomohiro
  • Journal Title: Bulletin of the Chemical Society of Japan Volume: 94 Issue: 1 Pages: 21-23
  • DOI: 10.1246/bcsj.20200129
  • NAID: 130007968797
  • Peer Reviewed
• [Journal Article] Easily Separable Cyclic Oligosilanes with p‐Methoxyphenyl Groups and Their Stereoselective Functionalization (2021)
  • Author(s): Omatsu Yamato、Mizuhata Yoshiyuki、Tokitoh Norihiro
  • Journal Title: European Journal of Inorganic Chemistry Volume: 2021 Issue: 10 Pages: 1005-1012
  • DOI: 10.1002/ejic.202001076
  • Peer Reviewed
• [Journal Article] Alkali-Metal-Ion-Centered Sandwich Structures of 4-Bromophenyl[tris(pentafluorophenyl)]borates and Their Synthetic Utility (2021)
  • Author(s): Iwai Kento、Mizuhata Yoshiyuki、Tokitoh Norihiro
  • Journal Title: Organometallics Volume: 40 Issue: 5 Pages: 570-577
  • DOI: 10.1021/acs.organomet.0c00711
  • Peer Reviewed
• [Journal Article] Additive-free Conversions of Internal Alkynes by Phosphanylalumanes Producing P/Al Frustrated Lewis Pairs (2020)
  • Author(s): T. Yanagisawa, Y. Mizuhata, N. Tokitoh
  • Journal Title: ChemPlusChem Volume: - Issue: 5 Pages: 933-942
  • DOI: 10.1002/cplu.202000239
  • Peer Reviewed
• [Journal Article] Protonation-Assisted Conjugate Addition of Axially Chiral Enolates: Asymmetric Synthesis of β-Lactams with Contiguous Tetrasubstituted Stereocenters from α-Amino Acids via Memory of Chirality (2020)
  • Author(s): Kawabata Takeo、Yang Pan、Yoshimura Tomoyuki、Sasamori Takahiro、Tokitoh Norihiro、Morisaki Kazuhiro
  • Journal Title: HETEROCYCLES Volume: 101 Issue: 2 Pages: 664-664
  • DOI: 10.3987/com-19-s(f)56
  • Peer Reviewed
• [Journal Article] Visible-Transparent Aromatic Polymers Obtained by the Polycondensation of a Bis(trifluorovinyl)benzene with Bisphenols (2020)
  • Author(s): Agou Tomohiro、Yoshinari Kazuto、Shirai Tomohiro、Yamada Shigeyuki、Konno Tsutomu、Mizuhata Yoshiyuki、Tokitoh Norihiro、Yasuda Sana、Yamazaki Takashi、Fukumoto Hiroki、Kubota Toshio
  • Journal Title: Macromolecules Volume: 53 Issue: 8 Pages: 2942-2949
  • DOI: 10.1021/acs.macromol.0c00157
  • Peer Reviewed
• [Journal Article] Development of P- and N-Chirogenic Ligands Based on Chiral Induction from a Phosphorus Donor to a Nitrogen Donor in Palladium Complexes (2020)
  • Author(s): Takahiro Iwamoto, Yoshiyuki Mizuhata, Norihiro Tokitoh, Masaharu Nakamura
  • Journal Title: Organometallics Volume: 39 Issue: 10 Pages: 1672-1677
  • DOI: 10.1021/acs.organomet.0c00154
  • Peer Reviewed
• [Journal Article] Facile preparation of α,ω-diynes bearing a perfluoroalkylene linker -(CF2)n- (n = 4,6) and their application for Co- or Rh-catalyzed [2+2+2]cycloaddition reactions affording aromatic compounds with perfluoroalkylene units (2020)
  • Author(s): Agou Tomohiro、Saruwatari Shogo、Shirai Tomohiro、Kumon Tatsuya、Yamada Shigeyuki、Konno Tsutomu、Mizuhata Yoshiyuki、Tokitoh Norihiro、Sei Yoshihisa、Fukumoto Hiroki、Kubota Toshio
  • Journal Title: Journal of Fluorine Chemistry Volume: 234 Pages: 109512-109512
  • DOI: 10.1016/j.jfluchem.2020.109512
  • Peer Reviewed
• [Journal Article] 1,2-Insertion reactions of alkynes into Ge-C bonds of arylbromogermylene (2020)
  • Author(s): Sugahara Tomohiro、Espinosa Ferao Arturo、Rey Planells Alicia、Guo Jing-Dong、Aoyama Shin、Igawa Kazunobu、Tomooka Katsuhiko、Sasamori Takahiro、Hashizume Daisuke、Nagase Shigeru、Tokitoh Norihiro
  • Journal Title: Dalton Transactions Volume: 49 Issue: 21 Pages: 7189-7196
  • DOI: 10.1039/d0dt01223h
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Solvent-Dependent Mechanism and Stereochemistry of Mitsunobu Glycosylation with Unprotected Pyranoses (2020)
  • Author(s): Takeuchi Hironori、Fujimori Yusuke、Ueda Yoshihiro、Shibayama Hiromitsu、Nagaishi Masaru、Yoshimura Tomoyuki、Sasamori Takahiro、Tokitoh Norihiro、Furuta Takumi、Kawabata Takeo
  • Journal Title: Organic Letters Volume: 22 Issue: 12 Pages: 4754-4759
  • DOI: 10.1021/acs.orglett.0c01549
  • Peer Reviewed
• [Journal Article] Synthesis and Properties of Thiophene-Fused Thiopyrylium Salts (2020)
  • Author(s): Nagahora, N.; Kitahara, K.; Mizuhata, Y.; Tokitoh, N.; Shioji, K.; Okuma, K.
  • Journal Title: The Journal of Organic Chemistry Volume: 85 Issue: 12 Pages: 7748-7756
  • DOI: 10.1021/acs.joc.0c00364
  • Peer Reviewed
• [Journal Article] Insertion Reaction of Chalcogens into an Al-P Bond (2020)
  • Author(s): Mizuhata Yoshiyuki、Tokitoh Norihiro、Yanagisawa Tatsuya
  • Journal Title: HETEROCYCLES Volume: 100 Issue: 7 Pages: 1084-1084
  • DOI: 10.3987/com-20-14255
  • Peer Reviewed
• [Journal Article] Reaction of germabenzenylpotassium with TBDMSCl: Unusual trimerization of germabenzene skeletons (2020)
  • Author(s): Mizuhata Yoshiyuki、Fujimori Shiori、Tokitoh Norihiro
  • Journal Title: Phosphorus, Sulfur, and Silicon and the Related Elements Volume: 195 Issue: 11 Pages: 936-939
  • DOI: 10.1080/10426507.2020.1804187
  • Peer Reviewed
• [Journal Article] Discovery of Self‐Assembling Small Molecules as Vaccine Adjuvants (2020)
  • Author(s): Jin Shuyu、Vu Hue Thi、Hioki Kou、Noda Naotaka、Yoshida Hiroki、Shimane Toru、Ishizuka Shigenari、Takashima Ippei、Mizuhata Yoshiyuki、Beverly Pe Kathleen、Ogawa Tetsuya、Nishimura Naoya、Packwood Daniel、Tokitoh Norihiro、Kurata Hiroki、Yamasaki Sho、Ishii Ken J.、Uesugi Motonari
  • Journal Title: Angewandte Chemie International Edition Volume: 60 Issue: 2 Pages: 961-969
  • DOI: 10.1002/anie.202011604
  • NAID: 120006958092
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Conformational Control in Dirhodium(II) Paddlewheel Catalysts Supported by Chalcogen-Bonding Interactions for Stereoselective Intramolecular C?H Insertion Reactions (2020)
  • Author(s): Murai Takuya、Lu Wenjie、Kuribayashi Toshifumi、Morisaki Kazuhiro、Ueda Yoshihiro、Hamada Shohei、Kobayashi Yusuke、Sasamori Takahiro、Tokitoh Norihiro、Kawabata Takeo、Furuta Takumi
  • Journal Title: ACS Catalysis Volume: 11 Issue: 2 Pages: 568-578
  • DOI: 10.1021/acscatal.0c03689
  • Peer Reviewed
• [Journal Article] Helicenes Fused with Hexafluorocyclopentene (HFCP): Synthesis, Structure, and Properties (2020)
  • Author(s): Agou Tomohiro、Kohara Masaki、Tamura Yuuki、Yamada Keisuke、Shiitsuka Kazuki、Hosoya Takaaki、Mizuhata Yoshiyuki、Tokitoh Norihiro、Hayashi Yuki、Moronuki Yusuke、Ishii Akihiko、Tanaka Yusuke、Muranaka Atsuya、Uchiyama Masanobu、Yamada Shigeyuki、Konno Tsutomu、Fukumoto Hiroki、Kubota Toshio
  • Journal Title: European Journal of Organic Chemistry Volume: 2020 Issue: 12 Pages: 1871-1880
  • DOI: 10.1002/ejoc.202000152
  • Peer Reviewed
• [Journal Article] The formation of a 1,4-disilabenzene and its isomerization into a disilabenzvalene derivative (2019)
  • Author(s): Sugahara Tomohiro、Sasamori Takahiro、Tokitoh Norihiro
  • Journal Title: Dalton Transactions Volume: 48 Issue: 25 Pages: 9053-9056
  • DOI: 10.1039/c9dt01322a
  • Peer Reviewed
• [Journal Article] A Purified, Solvent-Intercalated Precursor Complex for Wide-Process-Window Fabrication of Efficient Perovskite Solar Cells and Modules (2019)
  • Author(s): Ozaki Masashi、Shimazaki Ai、Jung Mina、Nakaike Yumi、Maruyama Naoki、Yakumaru Shinya、Rafieh Alwani Imanah、Sasamori Takahiro、Tokitoh Norihiro、Ekanayake Piyasiri、Murata Yasujiro、Murdey Richard、Wakamiya Atsushi
  • Journal Title: Angewandte Chemie International Edition Volume: 58 Issue: 28 Pages: 9389-9393
  • DOI: 10.1002/anie.201902235
  • Peer Reviewed
• [Journal Article] Near‐Infrared Circularly Polarized Luminescence through Intramolecular Excimer Formation of Oligo(p‐phenyleneethynylene)s‐Based Double Helicates (2019)
  • Author(s): Miki Koji、Noda Takeru、Gon Masayuki、Tanaka Kazuo、Chujo Yoshiki、Mizuhata Yoshiyuki、Tokitoh Norihiro、Ohe Kouichi
  • Journal Title: Chemistry - A European Journal Volume: 25 Issue: 39 Pages: 9211-9216
  • DOI: 10.1002/chem.201901467
  • Peer Reviewed
• [Journal Article] Nature of the E---E' interactions (E, E' = O, S, Se, and Te) at naphthalene 1,8-positions with fine details of the structures: experimental and theoretical investigations (2019)
  • Author(s): Satoko Hayashi, Manabu Uegaito, Taro Nishide, Eiichiro Tanaka, Waro Nakanishi, Takahiro Sasamori, Norihiro Tokitoh and Mao Minoura
  • Journal Title: New J. Chem. Volume: 43 Issue: 36 Pages: 14224-14237
  • DOI: 10.1039/c9nj02198a
  • Peer Reviewed
• [Journal Article] Syntheses and Structures of Novel λ3,λ3-Phosphanylalumanes Fully Bearing Carbon Substituents and Their Substituent Effects (2019)
  • Author(s): Yanagisawa Tatsuya、Mizuhata Yoshiyuki、Tokitoh Norihiro
  • Journal Title: Inorganics Volume: 7 Issue: 11 Pages: 132-132
  • DOI: 10.3390/inorganics7110132
  • Peer Reviewed / Open Access
• [Journal Article] Synthesis and properties of perfluoroalkylated TIPS-pentacenes (2019)
  • Author(s): Agou Tomohiro、Suzuki Seima、Kanno Yasunori、Hosoya Takaaki、Fukumoto Hiroki、Mizuhata Yoshiyuki、Tokitoh Norihiro、Suda Yuki、Furukawa Shunsuke、Saito Masaichi、Kubota Toshio
  • Journal Title: Tetrahedron Volume: 75 Issue: 47 Pages: 130678-130678
  • DOI: 10.1016/j.tet.2019.130678
  • Peer Reviewed
• [Journal Article] Pentacyclic Ladder-Heteraborin Emitters Exhibiting High-Efficiency Blue Thermally Activated Delayed Fluorescence with an Ultrashort Emission Lifetime (2019)
  • Author(s): Agou Tomohiro, Matsuo Kyohei, Kawano Rei, Park In Seob, Hosoya Takaaki, Fukumoto Hiroki, Kubota Toshio, Mizuhata Yoshiyuki, Tokitoh Norihiro, Yasuda Takuma
  • Journal Title: ACS Materials Letters Volume: 2 Issue: 1 Pages: 28-34
  • DOI: 10.1021/acsmaterialslett.9b00433
  • Peer Reviewed / Int'l Joint Research
• [Presentation] ゲルマベンゼニルゲルミレン-ルイス塩基錯体の反応性 (2024)
  • Author(s): 西野龍平・時任宣博・山田容子・水畑吉行
  • Organizer: 日本化学会第104春季年会、船橋
• [Presentation] 2位に2価ゲルマニウムを有する1,2,3-トリゲルマビシクロ[1.1.0]ブタンの合成とその骨格変換 (2024)
  • Author(s): 内田大地・水畑吉行・時任宣博・山田容子・行本万里子
  • Organizer: 日本化学会第104春季年会、船橋
• [Presentation] メチレン架橋1,3-ビスゲルミレンの合成 (2023)
  • Author(s): 内田大地・水畑吉行・時任宣博・山田容子・行本万里子
  • Organizer: 第27回ケイ素化学協会シンポジウム、那須
• [Presentation] 単原子ゲルマニウム導入反応の開発とその活用 (2023)
  • Author(s): 水畑吉行・西野龍平・山田容子・時任宣博
  • Organizer: 第33回基礎有機化学討論会、岡山
• [Presentation] Unusual Heteroatom Exchange of a Germabenzenyl Anion Leading to a Novel Ge Transfer Reaction (2023)
  • Author(s): Tokitoh Norihiro
  • Organizer: Achievements in Molecular Inorganic Chemistry, Bonn, Germany
  • Int'l Joint Research / Invited
• [Presentation] Systematic Studies on Hevay Germaneamides (2023)
  • Author(s): Kanda Kazuaki、Yukimoto Mariko、Tokitoh Norihiro
  • Organizer: The 17th International Conference on the Coordination and Organometallic Chemistry of Germanium, Tin and Lead, August 2023, Wellington, New Zealand
  • Int'l Joint Research / Invited
• [Presentation] A Unique Germanium Atom Transfer Reaction via Unusual Nuclear Exchange of a Germabenzenyl Anion (2023)
  • Author(s): Yoshiyuki Mizuhata、Ryohei Nishino、Norihiro Tokitoh
  • Organizer: The 17th International Conference on the Coordination and Organometallic Chemistry of Germanium, Tin and Lead, August 2023, Wellington, New Zealand
  • Int'l Joint Research
• [Presentation] Synthesis of Germabenzenylgermylene Lewis-base Complexes Useful for Germanium Transfer (2023)
  • Author(s): Ryohei Nishino、Yoshiyuki Mizuhata、Norihiro Tokitoh
  • Organizer: The 17th International Conference on the Coordination and Organometallic Chemistry of Germanium, Tin and Lead, August 2023, Wellington, New Zealand
  • Int'l Joint Research
• [Presentation] Formation of a Novel Cyclic Germylene via a Kinetically Stabilized Germyne (2023)
  • Author(s): Uchida Daichi、Mizuhata Yoshiyuki、Tokitoh Norihiro、Yukimoto Mariko
  • Organizer: The 17th International Conference on the Coordination and Organometallic Chemistry of Germanium, Tin and Lead, August 2023, Wellington, New Zealand
  • Int'l Joint Research
• [Presentation] かさ高いベンジル基を有するゲルミレンの反応性 (2023)
  • Author(s): 内田大地、行本万里子、水畑吉行、時任宣博
  • Organizer: 日本化学会第103春季年会、野田
• [Presentation] かさ高い置換基を有するアニオン性ケイ素クラスターの性質 (2023)
  • Author(s): 伊地知渉、水畑吉行、時任 宣博
  • Organizer: 日本化学会第103春季年会、野田
• [Presentation] Ge原子供与体として働くルイス塩基配位ゲルマベンゼニルゲルミレンの合成 (2023)
  • Author(s): 西野龍平、水畑吉行、時任宣博
  • Organizer: 日本化学会第103春季年会、野田
• [Presentation] In Pursuit of Heteraazulenes Containing a Heavier Group 14 Element (2023)
  • Author(s): Oshiro Taku、Mizuhata Yoshiyuki、Tokitoh Norihiro
  • Organizer: International Conference on Main Group Synthesis and Catalysis (ICMGSC-2023), IISER TVM, India
  • Int'l Joint Research / Invited
• [Presentation] かさ高い置換基を有するペンタブロモジシラン前駆体を活用した新規ケイ素クラスターの合成 (2022)
  • Author(s): 伊地知渉、水畑吉行、時任宣博
  • Organizer: 第49回有機典型元素化学討論会、富山
• [Presentation] 新規ターフェニル型立体保護基を導入したハロスタンニレンの合成 (2022)
  • Author(s): 中西泰己、行本万里子、水畑吉行、時任宣博
  • Organizer: 第49回有機典型元素化学討論会、富山
• [Presentation] アリールブロモゲルミレンの炭素ーゲルマニウム結合への1,2-挿入反応 (2022)
  • Author(s): 笹森貴裕、菅原知紘、青山慎、井川和宣、友岡克彦、時任宣博、Espinosa Ferao Arturo
  • Organizer: 第49回有機典型元素化学討論会、富山
• [Presentation] In Pursuit of Heteraazulenes Containing a Heavier Group 14 Element (2022)
  • Author(s): Oshiro Taku、Mizuhata Yoshiyuki、Tokitoh Norihiro
  • Organizer: The 19th Korea-Japan Joint Symposium on Organometallic and Coordination Chemistry, Incheon, Korea
  • Int'l Joint Research / Invited
• [Presentation] Progress in the Chemistry of Stable Silenes (2022)
  • Author(s): Tokitoh Norihiro
  • Organizer: The 8th Asian Silicon Symposium (ASiS-8), Taipei, Taiwan
  • Int'l Joint Research / Invited
• [Presentation] ゲルマニウム輸送反応によるゲルマニウムクラスター化合物の生成と構造 (2022)
  • Author(s): 西野 龍平、水畑 吉行、時任 宣博
  • Organizer: 第26回ケイ素化学協会シンポジウム、静岡
• [Presentation] ゲルマベンゼニルアニオンを鍵としたゲルマニウム原子輸送反応 (2022)
  • Author(s): 西野龍平、笹山瑠人、水畑吉行、時任宣博
  • Organizer: 第32回基礎有機化学討論会、京都
• [Presentation] Unique Reactions of a Phosphanylalumane: New Insight in the Chemistry of Group13/15 Interelement Compounds, (2022)
  • Author(s): Yanagisawa Tatsuya、Mizuhata Yoshiyuki、Tokitoh Norihiro
  • Organizer: The 16th International Symposium on Inorganic Ring Systems (IRIS-16), TU Graz, Austria
  • Int'l Joint Research / Invited
• [Presentation] 未踏のヘテロ原子化合物を求めて (2022)
  • Author(s): 時任宣博
  • Organizer: 近畿化学協会ヘテロ原子部会懇話会、2022年2月24日
  • Invited
• [Presentation] 未踏分子の創製に基づく高周期典型元素の特性解明 (2022)
  • Author(s): 時任宣博
  • Organizer: 日本化学会第102春季年会 化学会賞受賞講演、2022年3月23日
  • Invited
• [Presentation] New Insight in the Chemistry of Metallabenzenyl Anions: In Pursuit of a Stable Silabenzenyl Anion (2021)
  • Author(s): Shingo TSUJI, Shiori FUJIMORI, Yoshiyuki MIZUHATA, Tsukasa MATSUO, and Norihiro TOKITOH
  • Organizer: The 19 th International Symposium on Silicon Chemistry, Toulouse, France July 5-11, 2021
  • Int'l Joint Research / Invited
• [Presentation] ケイ素および高周期14族元化合物に関する未踏化学の探求 (2021)
  • Author(s): 時任宣博
  • Organizer: 第25回ケイ素化学協会シンポジウム、2021年10月28日
  • Invited
• [Presentation] Synthesis of Unsaturated Silicon Clusters Utilizing Asymmetrically Substituted Disilanes (2021)
  • Author(s): Yamato Omatsu, Yoshiyuki Mizuhata, Norihiro Tokitoh
  • Organizer: 日本化学会第101春季年会
• [Presentation] ケイ素核置換フェニルアニオンの合成研究 (2021)
  • Author(s): 辻 紳吾・水畑吉行・松尾 司・時任宣博
  • Organizer: 日本化学会第101春季年会
• [Presentation] ゲルマベンゼニルカリウムと種々の求電子剤との反応 (2021)
  • Author(s): 笹山瑠人・水畑吉行・時任宣博
  • Organizer: 日本化学会第101春季年会
• [Presentation] ケイ素およびゲルマニウムを骨格元素として含む2-ヘテラアズレン類の合成 (2021)
  • Author(s): 大城 卓・水畑吉行・時任宣博
  • Organizer: 日本化学会第101春季年会
• [Presentation] 2-スタンナナフタレン-6族金属錯体の熱異性化によるスタンニレン錯体の生成とその反応性 (2021)
  • Author(s): 楊 奕・水畑吉行・時任宣博
  • Organizer: 日本化学会第101春季年会
• [Presentation] テトラアリールボラート骨格を分子内に有する双性イオン型トリアリールメチリウム塩の合成と分光学的特性 (2021)
  • Author(s): 岩井健人・水畑吉行・時任宣博
  • Organizer: 日本化学会第101春季年会
• [Presentation] 嵩高い置換基を導入したアミノゲルマンの合成と反応 (2021)
  • Author(s): 神田憲明・行本万里子・時任宣博
  • Organizer: 日本化学会第101春季年会
• [Presentation] 芳香族性を有するノルコロールリン錯体の合成研究 (2021)
  • Author(s): 順井裕太・水畑吉行・時任宣博
  • Organizer: 日本化学会第101春季年会
• [Presentation] 2-ゲルマアズレンの合成 (2020)
  • Author(s): 大城卓・水畑吉行・時任宣博
  • Organizer: 第24回ケイ素化学協会シンポジウム
• [Presentation] 2-ゲルマナフタレニルアニオンの合成と性質 (2020)
  • Author(s): 辻 紳吾・水畑吉行・時任宣博
  • Organizer: 基礎有機化学会 若手オンラインシンポジウム
• [Presentation] 理論化学との協奏に基づく元素化学の進展 (2020)
  • Author(s): 時任宣博
  • Organizer: 理論化学会キックオフシンポジウム
  • Invited
• [Presentation] Development of "Heavy Aryl Anions" (2020)
  • Author(s): Yoshiyuki Mizuhata, Shiori Fujimori, Shingo Tsuji, Ryuto Sasayama, Norihiro Tokitoh
  • Organizer: IRCCS The 3rd Joint International Symposium, Nagoya, Japan
  • Int'l Joint Research
• [Presentation] Reactivity of Germabenzenylpotassium (2020)
  • Author(s): Ryuto Sasayama, Yoshiyuki Mizuhata, Norihiro Tokitoh
  • Organizer: 日本化学会第100春季年会
• [Presentation] 2-ゲルマナフタレニルアニオンの合成と性質 (2020)
  • Author(s): 辻 紳吾・水畑吉行・時任宣博
  • Organizer: 日本化学会第100春季年会
• [Presentation] 1-ゲルマアズレン骨格を基盤とした低配位ゲルマニウム化合物の合成 (2020)
  • Author(s): 大城 卓・水畑吉行・時任宣博
  • Organizer: 日本化学会第100春季年会
• [Presentation] ケイ素上にアルキル基とクロロ基を有する環状オリゴシランの反応性 (2020)
  • Author(s): 尾松大和・水畑吉行・時任宣博
  • Organizer: 日本化学会第100春季年会
• [Presentation] アニオン性置換基を有するケイ素化学種の反応性の検討 (2020)
  • Author(s): 岩井健人・水畑吉行・時任宣博
  • Organizer: 日本化学会第100春季年会
• [Presentation] 高周期典型元素を含む新規なπ電子系の創出：「重い芳香族化合物」の化学を中心に (2019)
  • Author(s): 時任宣博
  • Organizer: 第52回有機金属若手の会夏の学校,倉敷
  • Invited
• [Presentation] New Developments in the Chemistry of Heavy Aryl Anions (2019)
  • Author(s): Norihiro Tokitoh
  • Organizer: 13th International Conference on Heteroatom Chemistry (ICHAC-13), Prague, Czech Republic
  • Int'l Joint Research / Invited
• [Presentation] The Reaction of Heavy Phenyl Anions with Chalcogen Source (2019)
  • Author(s): Yoshiyuki Mizuhata, Shiori Fujimori, Norihiro Tokitoh
  • Organizer: 13th International Conference on Heteroatom Chemistry (ICHAC-13), Prague, Czech Republic
  • Int'l Joint Research
• [Presentation] Synthesis and Reactivity of Novel Cyclic Oligosilanes Having Bulky Alkyl Substituents (2019)
  • Author(s): Yamato Omatsu, Yoshiyuki Mizuhata, Norihiro Tokitoh
  • Organizer: 13th International Conference on Heteroatom Chemistry (ICHAC-13), Prague, Czech Republic
  • Int'l Joint Research
• [Presentation] A Systematic Study on Metallabenzenyl Anions Substituted by a Heavier Group 14 Element (2019)
  • Author(s): Norihiro Tokitoh, Shingo Tsuji, Shiori Fujimori, Yoshiyuki Mizuhata
  • Organizer: The 7th Asian Silicon Symposium (ASiS-7), Singapore
  • Int'l Joint Research / Invited
• [Presentation] Synthetic Studies on Silabenzenyl Anion (2019)
  • Author(s): Shingo Tsuji, Yoshiyuki Mizuhata, Norihiro Tokitoh
  • Organizer: The 7th Asian Silicon Symposium (ASiS-7), Singapore
  • Int'l Joint Research
• [Presentation] Construction of Novel Group-14 Species Aming Tautomerizable Heavy Carbonyl Compounds (2019)
  • Author(s): Mariko Yukimoto, Min Woo Jo, Norihiro Tokitoh
  • Organizer: The 7th Asian Silicon Symposium (ASiS-7), Singapore
  • Int'l Joint Research
• [Presentation] New Insights in the Chemistry of Heavy Aryl Anions (2019)
  • Author(s): Norihiro Tokitoh, Shiori Fujimori, Yoshiyuki Mizuhata
  • Organizer: The 16th International Conference on the Coordination and Organometallic Chemistry of Germanium, Tin, and Lead (ICCOC-GTL 2019), Saitama, Japan
  • Int'l Joint Research / Invited
• [Presentation] Generation and Properties of Heavy Phenoxide (2019)
  • Author(s): Yoshiyuki Mizuhata, Shiori Fujimori, Norihiro Tokitoh
  • Organizer: The 16th International Conference on the Coordination and Organometallic Chemistry of Germanium, Tin, and Lead (ICCOC-GTL 2019), Saitama, Japan
  • Int'l Joint Research
• [Presentation] In Pursuit of Unsaturated Heavier Main Group Element Compounds (2019)
  • Author(s): Norihiro Tokitoh
  • Organizer: Workshop 2019 (DAAD/IPID4all funding program), Bonn, Germany
  • Int'l Joint Research / Invited
• [Presentation] 高周期14族元素に核置換したアリールアニオンの開発 (2019)
  • Author(s): 水畑吉行
  • Organizer: 第17回有機合成化学協会関西支部賞受賞講演会, 大阪
  • Invited
• [Presentation] Recent Progress in the Chemistry of Heavy Aromatics (2019)
  • Author(s): Norihiro Tokitoh
  • Organizer: International Conference on Phosphorus, Boron and Silicon (PBSi 2019), Rome, Italy
  • Int'l Joint Research / Invited
• [Book] "Germaaromatic Compounds" in "Organogermanium Compounds: Theory, Experiment, and Applications", ed. by V. Ya. Lee (2023)
  • Author(s): Mizuhata Yoshiyuki、Tokitoh Norihiro
  • Total Pages: 29
  • Publisher: John Wiley & Sons, Inc.
• [Remarks] 有機元素化学研究室
  • URL: https://www.scl.kyoto-u.ac.jp/~oec/index.html
• [Remarks] 有機元素化学研究室
  • URL: http://oec.kuicr.kyoto-u.ac.jp/~tokitohlab/index.html
• [Remarks] 有機元素化学研究室
  • URL: http://oec.kuicr.kyoto-u.ac.jp/~tokitohlab/
• [Remarks] P-Al結合を利用したアルキンの変換で反応性化学種を創製 ~新たな小分子活性化の展開~
  • URL: https://www.kuicr.kyoto-u.ac.jp/sites/topics/200629/
• [Remarks] 時任研究室
  • URL: http://oec.kuicr.kyoto-u.ac.jp/~tokitohlab/