Synthesis of functional molecules by utilizing feature of bicyclic framework and exploration of thier novel properties

• Project/Area Number: 15K17825
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Organic chemistry
• Research Institution: Ehime University
• Principal Investigator: Mori Shigeki 愛媛大学, 学術支援センター, 助教 (30572028)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Project Status: Completed (Fiscal Year 2017)
• Budget Amount: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000); Fiscal Year 2017: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000); Fiscal Year 2016: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000); Fiscal Year 2015: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
• Keywords: π-共役化合物 / ポルフィリン / 二環性骨格 / 単結晶X線構造解析 / Diels-Alder反応 / 希土類金属錯体 / 積層型金属錯体 / 包摂錯体

Outline of Final Research Achievements

In this study, we synthesized novel functional compounds by utilizing two features of bicyclic skeleton (structural rigidity and skeletal transformation), and investigated their properties.
1) We succeeded in synthesizing the molecule tweezers in which the bicyclic moiety is [2.2.1] type (norbornadiene, NBD), and clarifying the inclusion behavior with C60, C70.
2) We have synthesized benzoporphyrin triple-decker type rare earth metal complex in which the number of fused benzene rings is increased to 2 (2 isomers) and 3, 4, respectively. Their yields was improved to 70% or more. The structure of the obtained metal complex was determined by X-ray crystal structure analysis.

Research Products

• [Journal Article] Donor-acceptor type A2B2 porphyrins: synthesis, energy transfer, computational and electro- chemical studies (2017)
  • Author(s): Sudipta Das, Haamid R. Bhat, Naresh Balsukuri, Prakash C. Jha, Yutaka Hisamune, Masatoshi Ishida, Hiroyuki Furuta, Shigeki Mori and Iti Gupta
  • Journal Title: Inorganic Chemistry Frontiers Volume: 4 Issue: 4 Pages: 618-638
  • DOI: 10.1039/c6qi00558f
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Synthesis and crystal structure of pyrroloquinoline quinol (PQQH2) and pyrroloquinoline quinone (PQQ) (2017)
  • Author(s): Ikemoto Kazuto、Mori Shigeki、Mukai Kazuo
  • Journal Title: Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials Volume: 73 Issue: 3 Pages: 489-497
  • DOI: 10.1107/s2052520617002281
  • Peer Reviewed
• [Journal Article] Crystal Structure of a Six-coordinated [5,10,15,20-Tetrakis(2,4,6-trimethylphenyl)porphyrinato-<i>k</i>⁴<i>N</i>]iron(III) Complex with Two 3,5-Dimethylpyridine <i>N</i>-Oxides (2017)
  • Author(s): Ide Yuki、Hosoda Haruka、Ishimae Hiroki、Mori Shigeki、Ikeue Takahisa
  • Journal Title: X-ray Structure Analysis Online Volume: 33 Issue: 0 Pages: 49-51
  • DOI: 10.2116/xraystruct.33.49
  • NAID: 130005951866
  • ISSN: 1883-3578
  • Peer Reviewed
• [Journal Article] Synthesis and Properties of Bicyclo[2.2.2]octadiene- and Benzene-fusing Bis(thiaporphyrin)s (2017)
  • Author(s): Uno Hidemitsu、 Tagawa Kazunari、 Mori Shigeki、 Okujima Tetsuo、 Takase Masayoshi、 Nakae Takahiro
  • Journal Title: Bulletin of the Chemical Society of Japan Volume: 12 Issue: 12 Pages: 1375-1381
  • DOI: 10.1246/bcsj.20170257
  • NAID: 130006250398
  • Peer Reviewed
• [Journal Article] Spin-crossover between high-spin (S=5/2) and low-spin (S=1/2) states in six-coordinate iron(III) porphyrins having two pyridine-N oxide derivatives (2017)
  • Author(s): Y. Ide, N. Murai, H. Ishimae, M. Suzuki, S. Mori, M. Takahashi, M. Nakamura, K. Yoshimi, T. Ikeue
  • Journal Title: Dalton Trans. Volume: 46 Issue: 1 Pages: 242-249
  • DOI: 10.1039/c6dt03859j
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Diethyl N,N'-dimethylpyrrol[3,4-f]isoindole-1,7-dicarboxylate as a 14π-electronic aromatic compound with two azomethine-ylide moieties (2017)
  • Author(s): S. Hiraoka, H. Tahara, S. Mori, T Okujima, M. Takase, T. Nakae, and H. Uno
  • Journal Title: Tetrahedron Volume: 73 Issue: 7 Pages: 957-963
  • DOI: 10.1016/j.tet.2017.01.015
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Synthesis, Structure, and Optical Studies of Donor-Acceptor-Type Near-Infrared (NIR) Aza-Boron-Dipyrromethene (BODIPY) Dyes (2016)
  • Author(s): Naresh Balsukuri, Mohsin Y. Lone, Prakash C. Jha, Shigeki Mori, Iti Gupta
  • Journal Title: Chem. Asian J. Volume: 11 Issue: 10 Pages: 1572-1587
  • DOI: 10.1002/asia.201600167
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Donor acceptor type ferrocene substituted aza-BODIPYs: Synthesis, optical and electrochemical studies (2016)
  • Author(s): Naresh Balsukuri, Shigeki Mori, Iti Gupta
  • Journal Title: J. Porphyrins Phthalocyanines Volume: 20 Issue: 06 Pages: 719-729
  • DOI: 10.1142/s1088424616500693
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Near-Infrared Phosphorescent Iridium(III) Benzonorrole Complexes Possessing Pyridine-Based Axial Ligands (2016)
  • Author(s): Maurya, Y. K.; Ishikawa, T.; Kawabe, Y.; Ishida, M.; Toganoh, M.; Mori, S.; Yasutake, Y.; Fukatsu, S.; Furuta, H.
  • Journal Title: Inorg. Chem Volume: 55 Issue: 12 Pages: 6223-6230
  • DOI: 10.1021/acs.inorgchem.6b00853
  • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
• [Journal Article] Template Synthesis of Decaphyrin without Meso-Bridges: Cyclo[10]pyrrole (2016)
  • Author(s): T. Okujima, C. Ando, S. Agrawal, H. Matsumoto, S. Mori, K. Ohara, I. Hisaki, T. Nakae, M. Takase, H. Uno, and N. Kobayashi
  • Journal Title: journal of the American Chemical Society Volume: 138 Issue: 24 Pages: 7540-7543
  • DOI: 10.1021/jacs.6b04941
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Synthesis of cyclo[8]pyrrole-polyoxometalate double-decker complex (2016)
  • Author(s): T. Okujima, H. Matsumoto, S. Mori, T. Nakae, M. Takase, and H. Uno
  • Journal Title: Tetrahedron Lett. Volume: 57 Issue: 29 Pages: 3160-3162
  • DOI: 10.1016/j.tetlet.2016.06.021
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] A novel isoindole-containing polyaromatic hydrocarbon unexpectedly formed during the synthesis of meso-2,6-dichlorophenyl-substituted tribenzosubporphyrin (2016)
  • Author(s): Yuta Shiina, Hideaki Karasaki, Shigeki Mori, Nagao Kobayashi, Hiroyuki Furuta, Soji Shimizu
  • Journal Title: Journal of Porphyrins and Phthalocyanines Volume: 20 Issue: 08n11 Pages: 1049-1054
  • DOI: 10.1142/s1088424616500541
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Synthesis of Hexagonal Shape-Persistent Cyclophane with D2h Symmetry (2016)
  • Author(s): Kazunari Tagawa, Shigeki Mori, Masayoshi Takase, Tetsuo Okujima, Ichiro Hisaki, Hidemitsu Uno
  • Journal Title: Tetrahedron Lett. Volume: 57 Issue: 36 Pages: 4079-4081
  • DOI: 10.1016/j.tetlet.2016.07.086
  • Peer Reviewed
• [Journal Article] Supramolecular Dimeric Structures of Pyrazole-containing Meso-Oxo Carbaphlorin Analogues (2016)
  • Author(s): Ishida, M.; Fujimoto, H.; Morimoto, T.; Mori, S.; Toganoh, M.; Shimizu, S.; Furuta, H.
  • Journal Title: Supramol. Chem. Volume: 28 Issue: 1 Pages: 8-16
  • DOI: 10.1080/10610278.2016.1158408
  • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
• [Journal Article] Design and synthesis of BODIPY-clickate based Hg2+ sensors: the effect of triazole binding mode with Hg2+ on signal transduction (2016)
  • Author(s): Mani Vedamalai, Dhaval Kedaria, Rajesh Vasita, Shigeki Mori, Iti Gupta
  • Journal Title: Dalton Trans. Volume: 45 Issue: 6 Pages: 2700-2708
  • DOI: 10.1039/c5dt04042f
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Near-infrared luminescent Sn(IV) complexes of N-confused tetraphenylporphyrin: Effect of axial anion coordination (2015)
  • Author(s): Arghya Basu, Motoki Kitamura, Shigeki Mori, Masatoshi Ishida, Yongshu Xie, Hiroyuki Furuta
  • Journal Title: J. Porphyrins Phthalocyanines Volume: 19 Issue: 01-03 Pages: 361-371
  • DOI: 10.1142/s1088424615500212
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Stable π-Radical from a Contracted Doubly N-Confused Hexaphyrin by Bis-Palladium Metallation (2015)
  • Author(s): Y. Hisamune, K. Nishimura, K. Isakari, M. Ishida, S. Mori, Satoru. Karasawa, T. Kato, Sangsu L., D.Kim, and H. Furuta,
  • Journal Title: Angew. Chem., Int. Ed. Engl. Volume: 54 Issue: 25 Pages: 7323-7327
  • DOI: 10.1002/anie.201502285
  • Peer Reviewed
• [Journal Article] Bridged Bis-BODIPYs: their synthesis, structures and properties (2015)
  • Author(s): Praseetha E. Kesavan, Sudipta Das, Mohsin Y Lone, Prakash Chandra Jha, Shigeki Mori, Iti Gupta
  • Journal Title: Dalton Trans. Volume: 44 Issue: 39 Pages: 17209-17221
  • DOI: 10.1039/c5dt01925g
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Benzo[c,d]indole-Containing Aza-BODIPY Dyes: Asymmetrization-Induced Solid-State Emission and Aggregation-Induced Emission Enhancement as New Properties of a Well-Known Chromophore (2015)
  • Author(s): Soji Shimizu, Ai Murayama, Takuya Haruyama, Taku Iino, Shigeki Mori, Hiroyuki Furuta, Nagao Kobayashi
  • Journal Title: Chem. Eur. J. Volume: 21 Issue: 37 Pages: 12996-13003
  • DOI: 10.1002/chem.201501464
  • Peer Reviewed
• [Presentation] Synthesis, Characterization, and Inclusion Behavior of Bisporphyrin with Two BCOD Units (2018)
  • Author(s): Shigeki Mori, Naoki Kawamoto, Masayoshi Takase, Tetsuo Okujima, Hidemitsu Uno
  • Organizer: International Congress on Pure & Applied Chemistry (ICPAC) 2018
  • Int'l Joint Research / Invited
• [Presentation] 新規ポルフィリン積層型希土類金属錯体の合成 (2018)
  • Author(s): 宮本 侃, 小林 朋広, 森 重樹, 髙瀬 雅祥, 奥島 鉄雄, 宇野 英満
  • Organizer: 日本化学会第98春季年会
• [Presentation] クリセン型連結部位を有するポルフィリン二量体の光学分割の検討 (2018)
  • Author(s): 秋成 諒哉, 河本 直樹, 森 重樹, 髙瀬 雅祥, 奥島 鉄雄, 宇野 英満
  • Organizer: 日本化学会第98春季年会
• [Presentation] 二環性骨格の特性を活かした共役系化合物の合成と性質 (2017)
  • Author(s): 森 重樹
  • Organizer: 構造有機化学若手研究者・研究会2017
• [Presentation] 積層型ベンゾポルフィリン希土類金属錯体の合成と1H NMRによる回転挙動の解明 (2017)
  • Author(s): 宮本 侃, 小林 朋広, 森 重樹, 髙瀬 雅祥, 奥島 鉄雄, 宇野 英満
  • Organizer: 2017ハロゲン利用ミニシンポジウム（第10回臭素化学懇話会年会）
• [Presentation] ベンゾポルフィリン希土類錯体の合成と物性評価 (2016)
  • Author(s): 小林朋広, 森 重樹, 髙瀬雅祥, 奥島鉄雄, 宇野英満
  • Organizer: 日本化学会中国四国支部大会
  • Place of Presentation: 香川大学（香川県・高松）
  • Year and Date: 2016-11-05
• [Presentation] Synthesis and Properties of Bisporphyrins with Two Bicyclic Units (2016)
  • Author(s): Shigeki Mori, Naoki Kawamoto, Masayoshi Takase, Tetsuo Okujima, Hidemitsu Uno
  • Organizer: International Conference on Porphyrin and Phthalocyaninenes (ICPP-9)
  • Place of Presentation: Nanjing (China)
  • Year and Date: 2016-07-03
• [Presentation] ノルボルナジエン骨格を有するピンセット型分子の合成及びフラーレン類との錯体形成挙動の評価 (2016)
  • Author(s): 竹花諒介, 森 重樹, 高瀬雅祥, 奥島鉄雄, 宇野英満
  • Organizer: 第14回ホスト・ゲスト化学シンポジウム HGCS2016
  • Place of Presentation: 高知城ホール（高知県・高知）
  • Year and Date: 2016-06-04
  • Int'l Joint Research
• [Presentation] ベンゾポルフィリン希土類金属錯体の合成と物性評価 (2016)
  • Author(s): 小林朋広, 森 重樹, 髙瀬雅祥, 奥島鉄雄, 宇野英満
  • Organizer: 日本化学会第97春季年会
  • Place of Presentation: 同志社大学（京都府・京田辺市）
  • Year and Date: 2016-03-24
• [Presentation] Synthesis and properties of bisporphyrin connected by chrysene-like bridge with two bicyclic skeletons (2015)
  • Author(s): Shigeki Mori, Naoki Kawamoto, Tetsuo Okujima, Hidemitsu Uno
  • Organizer: The International Chemical Congress of Pacific Basin Societies (PACIFICHEM2015)
  • Place of Presentation: Honolulu, USA
  • Year and Date: 2015-12-15
  • Int'l Joint Research
• [Presentation] 二環性骨格を有するクリセン型架橋ポルフィリン二量体の性質とキラル分割 (2015)
  • Author(s): 森 重樹, 河本直樹, 髙瀬雅祥, 奥島鉄雄, 宇野英満
  • Organizer: 第42回有機典型元素化学討論会
  • Place of Presentation: 名古屋大学（愛知県・名古屋市）
  • Year and Date: 2015-12-03
• [Presentation] ベンゾポルフィリン希土類金属錯体の合成 (2015)
  • Author(s): 小林朋広, 森 重樹, 奥島鉄雄, 髙瀬雅祥, 宇野英満
  • Organizer: 第42回有機典型元素化学討論会
  • Place of Presentation: 名古屋大学（愛知県・名古屋市）
  • Year and Date: 2015-12-03
• [Presentation] ベンゾポルフィリン希土類金属錯体の合成 (2015)
  • Author(s): 小林朋広, 森 重樹, 奥島鉄雄, 髙瀬雅祥, 宇野英満
  • Organizer: 第26回基礎有機化学討論会
  • Place of Presentation: 愛媛大学、松山大学（愛媛県・松山市）
  • Year and Date: 2015-09-24
• [Presentation] Substituents Introduction into Porphyrin Peripherals by Diels-Alder Reaction (2015)
  • Author(s): Shigeki Mori, Tomoko Yoshinouchi, Tetsuo Okujima, Masayoshi Takase, Hidemitsu Uno
  • Organizer: International Workshop of Molecular Architectonics (IWMA2015)
  • Place of Presentation: Shiretoko Grand Hotel "Kita-Kobushi", Shiretoko
  • Year and Date: 2015-08-03
  • Int'l Joint Research
• [Presentation] ベンゾポルフィリンLa錯体の合成 (2015)
  • Author(s): 小林朋広, 森 重樹, 奥島鉄雄, 宇野英満
  • Organizer: 第82回日本分析化学会有機微量分析研究懇談会
  • Place of Presentation: 愛媛大学（愛媛県・松山市）
  • Year and Date: 2015-05-28
• [Presentation] 二環性骨格の特性を活かしたポルフィリン類の合成と性質 (2015)
  • Author(s): 森 重樹
  • Organizer: 第8回 中国四国地区錯体化学研究会
  • Place of Presentation: 島根大学（島根県・松江市）
  • Year and Date: 2015-04-25
  • Invited