清水 章弘 (Dr. Akihiro Shimizu)

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学歴 Education

2005.3大阪大学理学部 化学科 卒業 (中筋一弘 教授)
2007.3大阪大学大学院理学研究科 化学専攻 博士前期課程 修了 (久保孝史 教授)
2009.12大阪大学大学院理学研究科 化学専攻 博士後期課程 修了 (久保孝史 教授)
2009.12博士 (理学) 大阪大学

職歴 Professional Career

2007.4日本学術振興会 特別研究員(DC1)
2007.11ベルギー、ノートルダム・ド・ラペ大学、訪問研究員
(Benoît Champagne主任研究員 (現教授)、3ヶ月間)
2010.1大阪大学大学院基礎工学研究科 物質創成専攻 助教 (戸部義人 教授 研究室)
2011.5京都大学大学院工学研究科 合成・生物化学専攻 助教 (吉田潤一 教授 研究室)

受賞歴 Awards

2009.4日本化学会第89春季年会 学生講演賞
2012.4日本化学会第92春季年会 優秀講演賞(学術)
2015.12有機合成化学協会 2015年 旭化成ファーマ研究企画賞
2016.6電気化学会 有機電子移動化学研究会 有機電子移動化学奨励賞
2017.3日本化学会第97春季年会 第31回若い世代の特別講演証

論文 List of Publications

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Original Papers

46. Liquid Quinones for Solvent-Free Redox Flow Batteries
Akihiro Shimizu, Keisuke Takenaka, Naoyuki Handa, Toshiki Nokami, Toshiyuki Itoh, Jun-Ichi Yoshida*
Adv. Mater. in press.

45. New Approach to 1,4-Benzoxazin-3-ones by Electrochemical C,H-Amination
Lars Julian Wesenberg, Sebastian Herold, Akihiro Shimizu, Jun-ichi Yoshida, Siegfried R. Waldvogel*
Chem. Eur. J. 2017, 23, 12096–12099.
Selected as a VIP. Selected as Cover Feature. DOI: 10.1002/chem.201703421

44. Fluoreno[2,3-b]fluorene vs. Indeno[2,1-b]fluorene: UnusualRelationship Between the Number of π Electrons and Excitation Energy in meta-Quinodimethane Type Singlet Diradicaloids
Hirokazu Miyoshi, Masahito Miki, Shintaro Hirano, Akihiro Shimizu, Ryohei Kishi, Kotaro Fukuda, Daisuke Shiomi, Kazunobu Sato, Takeji Takui, Ichiro Hisaki, Masayoshi Nakano,* Yoshito Tobe*
J. Org. Chem. 2017, 82, 1380–1388. DOI: 10.1021/acs.joc.6b02500

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43. Metal-Free Benzylic C-H Amination via Electrochemically Generated Benzylaminosulfonium Ions
Ryutaro Hayashi, Akihiro Shimizu, Yetao Song, Yosuke Ashikari, Toshiki Nokami, Jun-ichi Yoshida*
Chem. Eur. J. 2017, 23, 61–64. DOI: 10.1002/chem.201604484

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42. The Stabilized Cation Pool Method: Metal- and Oxidant-Free Benzylic C-H/Aromatic C-H Cross-Coupling
Ryutaro Hayashi, Akihiro Shimizu, Jun-ichi Yoshida*
J. Am. Chem. Soc. 2016, 138, 8400–8403. DOI: 10.1021/jacs.6b05273

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41. Generation, Characterization, and Reactions of Thionium Ions Based on the Indirect Cation Pool Method
Akihiro Shimizu, Keiji Takeda, Shota Mishima, Kodai Saito, Songhee Kim, Toshiki Nokami, Jun-ichi Yoshida*
Bull. Chem. Soc. Jpn. 2016, 89, 61–66. DOI: 10.1246/bcsj.20150323

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40. PPV Polymerization via the Gilch Route: Diradical Character of Monomers
Jelena Đurđević Nikolić, Sebastian Wouters, Julia Romanova, Akihiro Shimizu, Benoit Champagne,* Thomas Junkers, Dirk Vanderzande, Dimitri Van Neck, Michel Waroquier, Veronique Van Speybroeck, Saron Catak*
Chem. Eur. J. 2015, 21, 19176–19185. DOI: 10.1002/chem.201501900

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39. Heterocyclization Approach for Electrooxidative Coupling of Functional Primary Alkylamines with Aromatics
Tatsuya Morofuji, Akihiro Shimizu, Jun-ichi Yoshida*
J. Am. Chem. Soc. 2015, 137, 9816–9819. DOI: 10.1021/jacs.5b06526
Highlighted in Spotlights on Recent JACS Publications. J. Am. Chem. Soc. 2015, 137, 10017–10017. DOI: 10.1021/jacs.5b08475

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38. Automated Electrochemical Assembly of the Protected Potential TMG-Chitotriomycin Precursor Based on Rational Optimization of the Carbohydrate Building Block
Toshiki Nokami,* Yuta Isoda, Norihiko Sasaki, Aki Takaiso, Shuichi Hayase, Toshiyuki Itoh,* Akihiro Shimizu, Ryutaro Hayashi, Jun-ichi Yoshida*
Org. Lett. 2015, 17, 1525–1528. DOI: 10.1021/acs.orglett.5b00406

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37. Switching the Reaction Pathways of Electrochemically Generated -Haloalkoxysulfonium Ions - Synthesis of Halohydrins and Epoxides
Akihiro Shimizu, Ryutaro Hayashi, Yosuke Ashikari, Toshiki Nokami, Jun-ichi Yoshida*
Beilstein J. Org. Chem. 2015, 11, 242–248. DOI: 10.3762/bjoc.11.27

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36. Electrochemical Intramolecular C−H Amination: Synthesis of Benzoxazoles and Benzothiazoles
Tatsuya Morofuji, Akihiro Shimizu, Jun-ichi Yoshida*
Chem. Eur. J. 2015, 21, 3211–3214. DOI: 10.1002/chem.201406398
Highlighted in Angew. Chem. Int. Ed. Angew. Chem. Int. Ed. 2015, 54, 6398–6399.
DOI: 10.1002/anie.201502638

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35. Tetracyclopenta[def,jkl,pqr,vwx]tetraphenylene: A Potential Tetraradicaloid Hydrocarbon
Shunpei Nobusue, Hirokazu Miyoshi, Akihiro Shimizu, Ichiro Hisaki, Kotaro Fukuda, Masayoshi Nakano, Yoshito Tobe*
Angew. Chem. Int. Ed. 2015, 54, 2090–2094. DOI: 10.1002/anie.201410791
Selected as a VIP. Selected as Inside Cover. DOI: 10.1002/anie.201412137
Highlighted in ChemistryViews 28 January, 2015

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34. Redox Active Dendronized Polystyrenes Equipped with Peripheral Triarylamines
Toshiki Nokami, Naoki Musya, Tatsuya Morofuji, Keiji Takeda, Masahiro Takumi, Akihiro Shimizu, Jun-ichi Yoshida*
Beilstein J. Org. Chem. 2014, 10, 3097–3103. DOI: 10.3762/bjoc.10.326

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33. Transformation of Octadehydrodibenzo[12]annulene to Benzonaphthopentalene by Successive Nucleophilic and Electrophilic Transannular Cyclizations
Shunpei Nobusue, Ayumi Yoshizaki, Masahito Miki, Hirokazu Miyoshi, Akihiro Shimizu, Yoshito Tobe*
Tetrahedron 2014, 70, 8474–8479. DOI: 10.1016/j.tet.2014.09.079

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32. Introduction of Two Lithiooxycarbonyl Groups Enhances Cyclability of Lithium Batteries with Organic Cathode Materials
Akihiro Shimizu, Hiroki Kuramoto, Yutaka Tsujii, Toshiki Nokami, Yuu Inatomi, Nobuhiko Hojo, Hirotetsu Suzuki, Jun-ichi Yoshida*
J. Power Sources 2014, 260, 211–217. DOI: 10.1016/j.jpowsour.2014.03.027

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31. Direct C−N Coupling of Imidazoles with Aromatic and Benzylic Compounds via Electrooxidative C−H Functionalization
Tatsuya Morofuji, Akihiro Shimizu, Jun-ichi Yoshida*
J. Am. Chem. Soc. 2014, 136, 4496–4499. DOI: 10.1021/ja501093m
Highlighted in Spotlights on Recent JACS Publications. J. Am. Chem. Soc. 2014, 136, 5179−5180. DOI: 10.1021/ja503143p

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30. Nitrogen-Containing Polycyclic Quinones as Cathode Materials for LIB with Improved Voltage
Akihiro Shimizu, Yutaka Tsujii, Hiroki Kuramoto, Toshiki Nokami, Yuu Inatomi, Nobuhiko Hojo, Jun-ichi Yoshida*
Energy Technol. 2014, 2, 155–158. DOI: 10.1002/ente.201300148

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29. Benz[c]indeno[2,1-a]fluorene: A 2,3-Naphthoquinodimethane Incorporated into an Indenofluorene Frame
Hirokazu Miyoshi, Shunpei Nobusue, Akihiro Shimizu, Ichiro Hisaki, Mikiji Miyata, Yoshito Tobe*
Chem. Sci. 2014, 5, 163–168. DOI: 10.1039/C3SC52622D

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28. Synthesis and Physical Properties of Zethrene Derivatives Bearing Donor/Acceptor Substituents at 7,14-Positions
Daijiro Hibi, Kenichi Kitabayashi, Akihiro Shimizu, Rui Umeda, Yoshito Tobe*
Org. Biomol. Chem. 2013, 11, 8256–8261. DOI: 10.1039/C3OB41674G

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27. Halogen and Chalcogen Cation Pools Stabilized by DMSO. Versatile Reagents for Alkene Difunctionalization
Yosuke Ashikari, Akihiro Shimizu, Toshiki Nokami, Jun-ichi Yoshida*
J. Am. Chem. Soc. 2013, 135, 16070–16073. DOI: 10.1021/ja4092648

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26. Automated Solution-Phase Synthesis of Oligosaccharides via Iterative Electrochemical Assembly of Thioglycosides
Toshiki Nokami,* Ryutaro Hayashi, Yoshihiro Saigusa, Akihiro Shimizu, Chih-Yueh Liu, Kwok-Kong Tony Mong, Jun-ichi Yoshida*
Org. Lett. 2013, 15, 4520–4523. DOI: 10.1021/ol402034g

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25. Indeno[2,1-b]fluorene: A 20-π-Electron Hydrocarbon with Very Low-Energy Light Absorption
Akihiro Shimizu, Ryohei Kishi, Masayoshi Nakano, Daisuke Shiomi, Kazunobu Sato, Takeji Takui, Ichiro Hisaki, Mikiji Miyata, Yoshito Tobe*
Angew. Chem. Int. Ed. 2013, 52, 6076–6079. DOI: 10.1002/anie.201302091
Selected as Back Cover. DOI: 10.1002/anie.201303391

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24. Electrochemical C−H Amination: Synthesis of Aromatic Primary Amines via N-Arylpyridinium Ions
Tatsuya Morofuji, Akihiro Shimizu, Jun-ichi Yoshida*
J. Am. Chem. Soc. 2013, 135, 5000–5003. DOI: 10.1021/ja402083e
Highlighted in Synfacts. Synfacts 2013, 9, 696. DOI: 10.1055/s-0033-1338914

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23. Oxidative Cyclodimerization After Tandem Cyclization of Dehydrobenzo[14]annulenes Induced by Alkyllithium
Syunpei Nobusue, Akihiro Shimizu, Kenji Hori, Ichiro Hisaki, Mikiji Miyata, Yoshito Tobe*
Angew. Chem. Int. Ed. 2013, 52, 4184–4188. DOI: 10.1002/anie.201210233
Selected as Inside Cover. DOI: 10.1002/anie.201301655
Highlighted in Synfacts. Synfacts 2013, 9, 616. DOI: 10.1055/s-0033-1338771

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22. Polymer-Bound Pyrene-4,5,9,10-tetraone for Fast-Charge and-Discharge Lithium-Ion Batteries with High Capacity
Toshiki Nokami, Takahiro Matsuo, Yuu Inatomi, Nobuhiko Hojo, Takafumi Tsukagoshi, Hiroshi Yoshizawa, Akihiro Shimizu, Hiroki Kuramoto, Kazutomo Komae, Hiroaki Tsuyama, Jun-ichi Yoshida*
J. Am. Chem. Soc. 2012, 134, 19694–19700. DOI: 10.1021/ja306663g

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21. Metal- and Chemical-Oxidant-Free C−H/C−H Cross-Coupling of Aromatic Compounds: The Use of Radical-Cation Pools
Tatsuya Morofuji, Akihiro Shimizu, Jun-ichi Yoshida*
Angew. Chem. Int. Ed. 2012, 51, 7259–7262. DOI: 10.1002/anie.201202788

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20. Aromaticity and π-Bond Covalency: Prominent Intermolecular Covalent Bonding Interaction of a Kekulé Hydrocarbon with Very Significant Singlet Biradical Character
Akihiro Shimizu, Yasukazu Hirao, Kouzou Matsumoto, Hiroyuki Kurata, Takashi Kubo,* Mikio Uruichi, Kyuya Yakushi
Chem. Commun. 2012, 48, 5629–5631. DOI: 10.1039/C2CC31955A

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19. Singlet Open-Shell Character of Conjugated Kekulé Molecules
Takashi Kubo,* Mitsuya Aoba, Akihiro Shimizu, Yasukazu Hirao, Kouzou Matsumoto, Hiroyuki Kurata, Masayoshi Nakano.
AIP Conf. Proc. 2012, 1504, 883–886. DOI: 10.1063/1.4771836

18. Theoretical Aspects on the Evaluation and Interpretation of the Third-Order Nonlinear Optical Properties of Diradical Compounds
Benoît Champagne,* Edith Botek, Akihiro Shimizu, Takashi Kubo,* Kenji Kamada, Koji Ohta,* Ryohei Kishi, Hitoshi Fukui, Hideaki Takahashi, Masayoshi Nakano*
AIP Conf. Proc. 2012, 1504, 844–847. DOI: 10.1063/1.4771826

17. Theoretical Consideration of Singlet Open-Shell Character of Polyperiacenes Using Clar's Aromatic Sextet Valence Bond Model and Quantum Chemical Calculations
Akihiro Shimizu, Yasukazu Hirao, Takashi Kubo, Masayoshi Nakano, Edith Botek, Benoît Champagne*
AIP Conf. Proc. 2012, 1504, 399–405. DOI: 10.1063/1.4771733

16. Synthesis, Crystal Structure, and Physical Properties of Sterically Unprotected Hydrocarbon Radicals
Takashi Kubo,* Yoshiki Katada, Akihiro Shimizu, Yasukazu Hirao, Kazunobu Sato, Takeji Takui, Mikio Uruichi, Kyuya Yakushi, Robert C. Haddon*
J. Am. Chem. Soc. 2011, 133, 14240–14243. DOI: 10.1021/ja2065768
Highlighted in Synfacts. Synfacts 2011, 1304. DOI: 10.1055/s-0031-1289391

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15. Indeno[2,1-a]fluorene: An Air-Stable o-Quinodimethane Derivative
Akihiro Shimizu, Yoshito Tobe*
Angew. Chem. Int. Ed. 2011, 50, 6906–6910. DOI: 10.1002/anie.201101950

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14. Electronic Structure of Delocalized Singlet Biradical Ph2-IDPL Solid Film
Kaname Kanai,* Yukiko Noda, Keita Kato, Takashi Kubo, Kai Iketaki, Akihiro Shimizu, Yukio Ouchi, Kazuhiro Nakasuji, Kazuhiko Seki
Phys. Chem. Chem. Phys. 2010, 12, 12570–12577. DOI: 10.1039/C0CP00178C

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13. Alternating Covalent Bonding Interactions in a One-Dimensional Chain of a Phenalenyl-Based Singlet Biradical Molecule Having Kekulé Structures
Akihiro Shimizu, Takashi Kubo,* Mikio Uruichi, Kyuya Yakushi, Masayoshi Nakano, Daisuke Shiomi, Kazunobu Sato, Takeji Takui, Yasukazu Hirao, Kouzou Matsumoto, Hiroyuki Kurata, Yasushi Morita, Kazuhiro Nakasuji
J. Am. Chem. Soc. 2010, 132, 14421–14428. DOI: 10.1021/ja1037287

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12. Synthesis, Structure, and Photophysical Properties of Dibenzo[de,mn]naphthacenes
Tsun-Cheng Wu, Chia-Hua Chen, Daijiro Hibi, Akihiro Shimizu, Yoshito Tobe, Yao-Ting Wu*
Angew. Chem. Int. Ed. 2010, 49, 7059–7062. DOI: 10.1002/anie.201001929

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11. Synthesis and Characterization of Teranthene: A Singlet Biradical Polycyclic Aromatic Hydrocarbon Having Kekulé Structures
Akihito Konishi, Yasukazu Hirao, Masayoshi Nakano, Akihiro Shimizu, Edith Botek, Benoît Champagne,* Daisuke Shiomi, Kazunobu Sato, Takeji Takui, Kouzou Matsumoto, Hiroyuki Kurata, Takashi Kubo*
J. Am. Chem. Soc. 2010, 132, 11021–11023. DOI: 10.1021/ja1049737
Highlighted in Synfacts. Synfacts 2010, 1238. DOI: 10.1055/s-0030-1258739
Highlighted in Angew. Chem. Int. Ed. Angew. Chem. Int. Ed. 2011, 50, 1756–1758.
DOI: 10.1002/anie.201006705

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10. Signature of Multiradical Character in Second Hyperpolarizabilities of Rectangular Graphene Nanoflakes
Hiroshi Nagai, Masayoshi Nakano,* Kyohei Yoneda, Ryohei Kishi, Hideaki Takahashi, Akihiro Shimizu, Takashi Kubo, Kenji Kamada, Koji Ohta, Edith Botek, Benoît Champagne
Chem. Phys. Lett. 2010, 489, 212–218. DOI: 10.1016/j.cplett.2010.03.013

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9. Singlet Diradical Character from Experiment
Kenji Kamada,* Koji Ohta, Akihiro Shimizu, Takashi Kubo,* Ryohei Kishi, Hideaki Takahashi, Edith Botek, Benoît Champagne,* Masayoshi Nakano*
J. Phys. Chem. Lett. 2010, 937–940. DOI: 10.1021/jz100155s

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8. Third-Order Nonlinear Optical Properties of Trigonal, Rhombic and Bow-Tie Graphene Nanoflakes with Strong Structural Dependence of Diradical Character
Kyohei Yoneda, Masayoshi Nakano,* Ryohei Kishi, Hideaki Takahashi, Akihiro Shimizu, Takashi Kubo, Kenji Kamada, Koji Ohta, Benoît Champagne, Edith Botek
Chem. Phys. Lett. 2009, 480, 278–283. DOI: 10.1016/j.cplett.2009.09.047

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7. Resonance Balance Shift in Stacks of Delocalized Singlet Biradical
Akihiro Shimizu, Mikio Uruichi, Kyuya Yakushi, Hiroyuki Matsuzaki, Hiroshi Okamoto, Masayoshi Nakano, Yasukazu Hirao, Kouzou Matsumoto, Hiroyuki Kurata, Takashi Kubo*
Angew. Chem. Int. Ed. 2009, 48, 5482–5486. DOI: 10.1002/anie.200901382

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6. Scanning Tunneling Microscopy Study of a Phenalenyl-Based Singlet Biradical on Graphite
Kai Iketaki,* Kaname Kanai, Akihiro Shimizu, Takashi Kubo, Zhi-Hong Wang, Yukio Ouchi, Yasushi Morita, Kazuhiro Nakasuji, Kazuhiko Seki
J. Phys. Chem. C 2009, 113, 1515–1519. DOI: 10.1021/jp808686v

5. Theoretical Study of Third-Order Nonlinear Optical Properties in Square Nanographenes with Open-Shell Singlet Ground States
Masayoshi Nakano,* Hiroshi Nagai, Hitoshi Fukui, Kyohei Yoneda, Ryohei Kishi, Hideaki Takahashi, Akihiro Shimizu, Takashi Kubo, Kenji Kamada, Koji Ohta, Benoît Champagne, Edith Botek
Chem. Phys. Lett. 2008, 467, 120–125. DOI: 10.1016/j.cplett.2008.10.084

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4. Ambipolar Organic Field-Effect Transistors Based on a Low Band Gap Semiconductor with Balanced Hole and Electron Mobilities
Masayuki Chikamatsu, Takefumi Mikami, Jiro Chisaka, Yuji Yoshida, Reiko Azumi, Kiyoshi Yase, Akihiro Shimizu, Takashi Kubo, Yasushi Morita, Kazuhiro Nakasuji
Appl. Phys. Lett. 2007, 91, 043506. DOI: 10.1063/1.2766696

3. Strong Two-Photon Absorption of Singlet Diradical Hydrocarbons
Kenji Kamada,* Koji Ohta, Takashi Kubo, Akihiro Shimizu, Yasushi Morita, Kazuhiro Nakasuji, Ryohei Kishi, Suguru Ohta, Shin-ichi Furukawa, Hideaki Takahashi, Masayoshi Nakano
Angew. Chem. Int. Ed. 2007, 46, 3544–3546. DOI: 10.1002/anie.200605061

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2. Singlet Biradical Character of Phenalenyl-Based Kekulé Hydrocarbon with Naphthoquinoid Structure
Takashi Kubo,* Akihiro Shimizu, Mikio Uruichi, Kyuya Yakushi, Masayoshi Nakano, Daisuke Shiomi, Kazunobu Sato, Takeji Takui, Yasushi Morita,* Kazuhiro Nakasuji*
Org. Lett. 2007, 9, 81–84. DOI: 10.1021/ol062604z

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1. Synthesis, Intermolecular Interaction, and Semiconductive Behavior of a Delocalized Singlet Biradical Hydrocarbon
Takashi Kubo,* Akihiro Shimizu, Maki Sakamoto, Mikio Uruichi, Kyuya Yakushi, Masayoshi Nakano, Daisuke Shiomi, Kazunobu Sato, Takeji Takui, Yasushi Morita, Kazuhiro Nakasuji*
Angew. Chem. Int. Ed. 2005, 44, 6564–6568. DOI: 10.1002/anie.200502303

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Accounts & Reviews

6. Electrogenerated Cationic Reactive Intermediates: The Pool Method and Further Advances
Jun-ichi Yoshida,* Akihiro Shimizu, Ryutaro Hayashi
Chem. Rev. accepted.

5. Reaction Integration Using Electrogenerated Cationic Intermediates
Jun-ichi Yoshida,* Akihiro Shimizu, Yosuke Ashikari, Tatsuya Morofuji, Ryutaro Hayashi, Toshiki Nokami, Aiichiro Nagaki
Bull. Chem. Soc. Jpn. 2015, 88, 763–775. DOI: 10.1246/bcsj.20150100

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4. Non-Alternant Non-Benzenoid Kekulenes: Birth of a New Kekulene Family
Hirokazu Miyoshi, Shunpei Nobusue, Akihiro Shimizu, Yoshito Tobe*
Chem. Soc. Rev. 2015, 44, 6560–6577. DOI: 10.1039/c5cs00185d

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3. Indenofluorene Congeners: Biradicaloids and Beyond
Akihiro Shimizu, Shunpei Nobusue, Hirokazu Miyoshi, Yoshito Tobe*
Pure Appl. Chem. 2014, 86, 517–528. DOI: 10.1515/pac-2014-5043

2. Experimental Consideration on Covalent Bonding Interactions in Stacks of Singlet Biradicals Having Kekulé Structures
Akihiro Shimizu, Masayoshi Nakano, Yasukazu Hirao, Takashi Kubo*
J. Phys. Org. Chem. 2011, 24, 876–882. DOI: 10.1002/poc.1873

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1. Chemistry of Phenalenyl-Based Delocalized Singlet Biradicals
Takashi Kubo,* Akihiro Shimizu, Masayoshi Nakano, Kazuhiro Nakasuji
J. Synth. Org. Chem. Jpn. 2010, 68, 64–74. DOI: 10.5059/yukigoseikyokaishi.68.64


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