Theoretical and experimental study on the photoinduced trans-cis isomerization of coumaric acid and its derivatives

• Project/Area Number: 25410017
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Physical chemistry
• Research Institution: Hiroshima University
• Principal Investigator: Ebata Takayuki 広島大学, 理学(系)研究科(研究院), 教授 (70142924)
• Co-Investigator(Kenkyū-buntansha): INOKUCHI YOSHIYA 広島大学, 大学院理学研究科, 准教授 (30311187)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Project Status: Completed (Fiscal Year 2015)
• Budget Amount: ¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000); Fiscal Year 2015: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2013: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
• Keywords: isomerization / intrenal conversion / coumaric acids / PYP / supersonic beam / laser spectroscopy / cinnamte derivatives / theoretical calculation / クマル酸 / 光誘起異性化反応 / レーザー分光 / 超音速分子線 / 低温マトリックス単離赤外分光 / 光異性化 / 無輻射過程

Outline of Final Research Achievements

Nonradiative process involving trans-cis isomerization of cinnamate and its derivatives has been studied experimentally and theoretically. The S1 lifetime measurements show that o- and m-substituted cinnamate is much longer than that of p-substituted cinnamate. In addition, the hydrogen-bonding to the carbonyl group shortens the S1 lifetime.

Research Products

• [Int'l Joint Research] AIX-Marseille University(France)
• [Journal Article] Cage Effect on Conformational Preference and Photophysics in the Host-Guest Complex of Benzenediols with 18-Crown-6 (2016)
  • Author(s): Fumiya Morishima, Ryoji Kusaka, Yoshiya Inokuchi, Takeharu Haino and Takayuki Ebata
  • Journal Title: Phys. Chem. Chem. Phys. Volume: 18 Issue: 11 Pages: 8027-8038
  • DOI: 10.1039/c5cp07171b
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Anomalous Cage Effect of the Excited State Dynamics of Catechol in the 18-Crown-6-Catechol Host--Guest Complex (2015)
  • Author(s): Fumiya Morishima, Ryoji Kusaka, Yoshiya Inokuchi, Takeharu Haino, and Takayuki Ebata
  • Journal Title: Journal of Physical Chemistry B Volume: 119 Issue: 6 Pages: 2557-2565
  • DOI: 10.1021/jp508619f
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Direct Spectroscopic Evidence of Photoisomerization in para-Methoxy Methylcinnamate Revealed by Low-Temperature Matrix-Isolation FTIR Spectroscopy (2015)
  • Author(s): Yasunori Miyazaki, Yoshiya Inokuchi, Nobuyuki Akai,and Takayuki Ebata
  • Journal Title: Journal of Physical Chemistry Letters Volume: 6 Issue: 7 Pages: 1134-1139
  • DOI: 10.1021/acs.jpclett.5b00203
  • NAID: 120005646505
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] UV photodissociation spectroscopy of cryogenic cooled gas phase host-guest complex ions of crown ethers (2015)
  • Author(s): Yoshiya Inokuchi, Takeharu Haino, Ryo Sekiya, Fumiya Morishima, Claude Dedonder, Geraldine Feraud, Christophe Jouve, Takayuki Ebata
  • Journal Title: Physical Chemistry Chemical Physics Volume: 17 Issue: 39 Pages: 25925-25934
  • DOI: 10.1039/c5cp01960e
  • NAID: 120005829505
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Solvent Effects on the Encapsulation of Divalent Ions by Benzo-18-Crown-6 and Benzo-15-Crown-5 (2015)
  • Author(s): Yoshiya Inokuchi, Takayuki Ebata, and Thomas R. Rizzo
  • Journal Title: J. Phys. Chem. A Volume: 119 Issue: 29 Pages: 8097-8105
  • DOI: 10.1021/acs.jpca.5b04450
  • NAID: 120006523856
  • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
• [Journal Article] Ultraviolet Photodissociation Spectroscopy of Cold K+Calix[4]arene Complex in the Gas Phase (2015)
  • Author(s): Yoshiya Inokuchi,Kazuki Soga, Kenta Hirai, Motoki Kida, Fumiya Morishima, and Takayuki Ebata
  • Journal Title: J. Phys. Chem. A Volume: 119 Issue: 31 Pages: 8512-8518
  • DOI: 10.1021/acs.jpca.5b05328
  • NAID: 120006523857
  • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
• [Journal Article] New insights into metal ion-crown ether complexes revealed by SEIRA spectroscopy (2015)
  • Author(s): Yoshiya Inokuchi, Takayuki Ebata, Toshiaki Ikeda, Takeharu Haino, Tetsunari Kimura, Hao Guo, Yuji Furutani
  • Journal Title: New Journal of Chemistry Volume: 39 Issue: 11 Pages: 8673-8680
  • DOI: 10.1039/c5nj01787d
  • NAID: 120005829506
  • Peer Reviewed / Open Access
• [Journal Article] IR Photodissociation Spectroscopy of (OCS)n+ and (OCS)n- Cluster Ions: Similarity and Dissimilarity in the Structures of CO2, OCS, and CS2 Cluster Ions (2015)
  • Author(s): Yoshiya Inokuchi and Takayuki Ebata
  • Journal Title: J. Chem. Phys. Volume: 142 Issue: 21 Pages: 214306-214312
  • DOI: 10.1063/1.4921991
  • NAID: 120005649420
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Formation of Host-Guest Complexes on Gold Surface Investigated by Surface-Enhanced IR Absorption Spectroscopy (2014)
  • Author(s): Inokuchi, Y., Mizuuchi, T., Ebata, T., Ikeda, T., Haino, T., Kimura, T., Guo, H., Furutani, Y
  • Journal Title: Chem. Phys. Lett Volume: 592 Pages: 90-95
  • DOI: 10.1016/j.cplett.2013.12.026
  • NAID: 120005615680
  • Peer Reviewed / Open Access
• [Journal Article] Microhydration Effects on the Encapsulation of Potassium Ion by Dibenzo-18-Crown-6 (2014)
  • Author(s): Y. Inokuchi, T. Ebata, T. R. Rizzo, and O. V. Boyarkin
  • Journal Title: J. Am. Chem. Soc. Volume: 136 Issue: 5 Pages: 1815-1824
  • DOI: 10.1021/ja4086066
  • NAID: 120005646503
  • Peer Reviewed / Open Access
• [Journal Article] Development of Ultraviolet-Ultraviolet Hole-Burning Spectroscopy for Cold Gas-Phase Ions (2014)
  • Author(s): Geraldine Feraud, Claude Dedonder, Christophe Jouvet, Yoshiya Inokuchi, Takeharu Haino, Ryo Sekiya, Takayuki Ebata
  • Journal Title: The Journal of Physical Chemistry Letters Volume: 5 Issue: 7 Pages: 1236-1240
  • DOI: 10.1021/jz500478w
  • NAID: 120006523855
  • Peer Reviewed / Open Access
• [Journal Article] Experimental and Theoretical Study on the Excited-State Dynamics of ortho-, meta-, and para-Methoxy Methylcinnamate (2014)
  • Author(s): Y. Miyazaki, K. Yamamoto, J. Aoki, T. Ikeda, Y. Inokuchi, M. Ehara, T. Ebata
  • Journal Title: J. Chem. Phys. Volume: 141 Issue: 24
  • DOI: 10.1063/1.4904268
  • NAID: 120005615681
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Microhydration Effects on the Intermediates of the SN2 Reaction of Iodide Anion with Methyl Iodide (2013)
  • Author(s): K. DOI:, E. Togano, S. S. Xantheas, R. Nakanishi, T. Nagata, T. Ebata, and Y. Inokuchi
  • Journal Title: Angew. Chem. Int. Volume: 52 Issue: 16 Pages: 4380-4383
  • DOI: 10.1002/anie.201207697
  • Peer Reviewed
• [Journal Article] Study on Vibrational Relaxation Dynamics of Phenol-Water Complex by Picosecond Time-Resolved IR-UV Pump-Probe Spectroscopy in a Supersonic Molecular Beam (2013)
  • Author(s): Y. Miyazaki, Y. Inokuchi, T. Ebata, and M. Petkovic
  • Journal Title: Chem. Phys. Volume: 419(16) Pages: 205-211
  • DOI: 10.1016/j.chemphys.2013.02.023
  • NAID: 120005649419
  • Peer Reviewed
• [Journal Article] Vibrational Spectroscopy of Picolinamide and Water: From Dimers to Condensed Phase (2013)
  • Author(s): V. Jovanovic;, Y. Miyazaki, T. Ebata, M. Petkovic;
  • Journal Title: J. Phys. Chem. A Volume: 117 Issue: 30 Pages: 6474-6482
  • DOI: 10.1021/jp402033c
  • Peer Reviewed
• [Journal Article] Structure and Hydrogen-Bonding Ability of Estrogens Studied in the Gas Phase (2013)
  • Author(s): F. Morishima, Y. Inokuchi, and T. Ebata
  • Journal Title: J. Phys. Chem. A Volume: 117(50) Issue: 50 Pages: 13543-13555
  • DOI: 10.1021/jp407438j
  • NAID: 120005646502
  • Peer Reviewed
• [Journal Article] Laser Spectroscopic Study of Cold Host-Guest Complexes of Crown Ethers in the Gas Phase (2013)
  • Author(s): Y. Inokuchi, R. Kusaka, T. Ebata, O. V. Boyarkin, and T. R. Rizzo
  • Journal Title: Chem Phys Chem. Volume: 14 Issue: 4 Pages: 649-660
  • DOI: 10.1002/cphc.201200746
  • NAID: 120005615677
  • Peer Reviewed
• [Presentation] Effect of Solvation on Conformation Preference of Inclusion Complexes (2016)
  • Author(s): Takayuki Ebata
  • Organizer: The 2016 Gordon Research Conference on Molecular and Ionic Clusters
  • Place of Presentation: Ventura CA, USA
  • Year and Date: 2016-01-17
  • Int'l Joint Research / Invited
• [Presentation] Experimental and theoretical study on the excited state dynamics of methyl cinnamate and its derivatives (2015)
  • Author(s): Takayuki Ebata
  • Organizer: Pacifichem2015
  • Place of Presentation: Honolulu Hawaii, USA
  • Year and Date: 2015-12-15
  • Int'l Joint Research / Invited
• [Presentation] UV photodissociation(UVPD) spectroscopy of M+calix[4]arene and M+4-tert-butyl-calix[4]arene complexes under the cold gas phase condition (2015)
  • Author(s): Kenta Hirai,Takayuki Ebata1,Yoshiya Inokuchi
  • Organizer: The 12th Nano Bio Info Chemistry Symposium
  • Place of Presentation: Hiroshima University
  • Year and Date: 2015-12-05
  • Int'l Joint Research
• [Presentation] 金属イオンーカリックスアレン錯体の極低温気相レーザー分光 (2015)
  • Author(s): 井口佳哉，曽我和毅，平井健太，木田基，江幡孝之
  • Organizer: 第９回分子科学討論会
  • Place of Presentation: 東京工業大学
  • Year and Date: 2015-09-16
• [Presentation] フェノール誘導体・・18crown6錯体における構造選択的包接 (2015)
  • Author(s): 森島史哉，井口佳哉，灰野岳晴，江幡孝之
  • Organizer: 第９回分子科学討論会
  • Place of Presentation: 東京工業大学
  • Year and Date: 2015-09-16
• [Presentation] 低温アルゴンマトリックス赤外分光法と超音速ジェット分光法による桂皮酸誘導体の光異性化の研究 (2015)
  • Author(s): 宮崎泰典，井口佳哉，江幡孝之，玉木愛梨，小島聡志，赤井伸行，金澤悠紀，江原正博
  • Organizer: 第９回分子科学討論会
  • Place of Presentation: 東京工業大学
  • Year and Date: 2015-09-16
• [Presentation] 極低温気相クラウンエーテル包接イオン錯体のレーザー分光 (2015)
  • Author(s): 江幡孝之，井口佳哉，森島史哉，灰野岳晴，関谷亮，Claude Dedoner, Christophe Jouvet
  • Organizer: 第９回分子科学討論会
  • Place of Presentation: 東京工業大学
  • Year and Date: 2015-09-16
• [Presentation] Laser spectroscopic study of cold gas phase functional molecular ions generated by ESI combined with Cold Ion-trap (2015)
  • Author(s): T. Ebata
  • Organizer: Gordon Research Conference on Gaseous Ions: Structures, Energetics & Reactions
  • Place of Presentation: Texas(USA)
  • Year and Date: 2015-02-22 – 2015-02-27
  • Invited
• [Presentation] 18-crown-6…benzenediol complex: changing of the S1 lifetime accompanied by structural modification (2014)
  • Author(s): F. Morishima, R. Kusaka, Y. Inokuchi, T. Haino, T. Ebata
  • Organizer: The 11th Nano Bio Info Chemistry Symposium
  • Place of Presentation: 東広島
  • Year and Date: 2014-12-13
• [Presentation] Excited-State Dynamics of Methyl Cinnamate Derivatives in Gas Phase (2014)
  • Author(s): K. Yamamoto1, J. Aoki, Y. Miyazaki, Y. Inokuchi1, M. Ehara, T. Ebata
  • Organizer: The 11th Nano Bio Info Chemistry Symposium
  • Place of Presentation: 東広島
  • Year and Date: 2014-12-13
• [Presentation] Structure and Cage Effect of Benzenediol---Crown ether Inclusion Complexes (2014)
  • Author(s): T. Ebata
  • Organizer: Core-to-core International Symposium on Ionization Induced Switching
  • Place of Presentation: Berlin (Germany)
  • Year and Date: 2014-12-12 – 2014-12-13
  • Invited
• [Presentation] Nonradiative decay dynamics of p-coumaric acid and its derivatives in the gas phase (2014)
  • Author(s): T. Ebata
  • Organizer: Chemical Physics of Molecules and Polyfunctional Materials
  • Place of Presentation: Orenburg (Russia)
  • Year and Date: 2014-10-29 – 2014-10-31
  • Invited
• [Presentation] クラウンエーテルの金属イオン包接に対する溶媒効果の研究 (2014)
  • Author(s): 井口佳哉，江幡孝之，T. Rizzo
  • Organizer: 第８回分子科学討論会
  • Place of Presentation: 東広島
  • Year and Date: 2014-09-21 – 2014-09-24
• [Presentation] 18-crown-6との錯体形成によるbenzenediolの構造と励起状態寿命の制御 (2014)
  • Author(s): 森島史哉，日下良二，井口佳哉，灰野岳晴，江幡孝之
  • Organizer: 第８回分子科学討論会
  • Place of Presentation: 東広島
  • Year and Date: 2014-09-21 – 2014-09-24
• [Presentation] メチルシンナメート誘導体の電子励起状態無輻射緩和の置換基および水素結合効果 (2014)
  • Author(s): 山本冠仁，江幡孝之，井口佳哉，宮崎泰典，江原正博
  • Organizer: 第８回分子科学討論会
  • Place of Presentation: 東広島
  • Year and Date: 2014-09-21 – 2014-09-24
• [Presentation] 表面増強赤外分光法によるクラウンエーテルの金属イオン包接現象の観測 (2014)
  • Author(s): 山内佑，池田俊明，灰野岳晴，江幡孝之
  • Organizer: 第８回分子科学討論会
  • Place of Presentation: 東広島
  • Year and Date: 2014-09-21 – 2014-09-24
• [Presentation] 偏光赤外スペクトル測定によるオキサアルカノール結晶の構造推定 (2014)
  • Author(s): 中山駿，福原幸一，江幡孝之
  • Organizer: 第８回分子科学討論会
  • Place of Presentation: 東広島
  • Year and Date: 2014-09-21 – 2014-09-24
• [Presentation] クラウンエーテル包接錯体のレーザー分光 (2014)
  • Author(s): 江幡孝之
  • Organizer: 第３１回シクロデキストリンシンポジウム
  • Place of Presentation: 島根
  • Year and Date: 2014-09-11 – 2014-09-12
  • Invited
• [Presentation] S1 excited state dynamics of OMpCA and its hydrogen-bonded complexes (2014)
  • Author(s): M. Yasunori,Y. Inokuchi,T. Ebata, M. Ehara
  • Organizer: 第３０回化学反応討論会
  • Place of Presentation: 姫路
  • Year and Date: 2014-06-04 – 2014-06-06
• [Presentation] Huge fluorescence lifetime elongation of catechol by comlexation with 18-crown-6 ether (2014)
  • Author(s): F. Morishima, R. Kusaka, Y. Inokuchi, T. Ebata
  • Organizer: 第３０回化学反応討論会
  • Place of Presentation: 姫路
  • Year and Date: 2014-06-04 – 2014-06-06
• [Presentation] Conformational preference in the 18C6…benzenediol complexes (2014)
  • Author(s): F. Morishima, Y. Inokuchi, T. Ebata
  • Organizer: Symposium on Molecular Science and Synthesis of Functional Molecules for Next Generation
  • Place of Presentation: 広島大学
• [Presentation] Development of laser spectroscopy for cold encapsulated ion complexes in gas phase (2014)
  • Author(s): K. Soga, T. Ebata, Y. Inokuchi
  • Organizer: Symposium on Molecular Science and Synthesis of Functional Molecules for Next Generation
  • Place of Presentation: 広島大学
• [Presentation] Excited-State Dynamics of Methyl Cinnamate Derivatives (2014)
  • Author(s): Y. Miyazaki, K. Yamamoto, J. Aoki, Y. Inokuchi, T. Ebata, M. Ehara
  • Organizer: Symposium on Molecular Science and Synthesis of Functional Molecules for Next Generation
  • Place of Presentation: 広島大学
• [Presentation] Study on vibrational dynamics of phenol-water complex in a supersonic molecular beam (2013)
  • Author(s): Y. Miyazaki、Y. Inokuchi、T. Ebata、M. Petkovic
  • Organizer: 29th symposium on chemical kinetics and dynamics
  • Place of Presentation: 仙台
• [Presentation] Structures and the hydrogen bonding ability of estrogens studied by supersonic jet/laser spectroscopy (2013)
  • Author(s): F. Morishima, Y. Inokuchi, T. Ebata
  • Organizer: 68th Ohio state university international symposium on molecular spectroscopy
  • Place of Presentation: オハイオ州立大学、米国
• [Presentation] クマル酸誘導体の無輻射緩和経路機構とダイナミックス (2013)
  • Author(s): 宮崎泰典、島田大樹、井口佳哉、江幡孝之、江原正広
  • Organizer: 第７回分子科学討論会
  • Place of Presentation: 京都
• [Presentation] p-methoxy methyl cinnamate の電子励起状態の異性化を含めた無輻射過程についての研究 (2013)
  • Author(s): 山本冠仁、宮崎康典、井口佳哉、江幡孝之
  • Organizer: 第７回分子科学討論会
  • Place of Presentation: 京都
• [Presentation] 金薄膜上に化学吸着させたクラウンエーテル金属イオン錯体の赤外分光 (2013)
  • Author(s): 水内喬裕、池田俊明、灰野岳晴、Guo Hao、木村哲就、古谷祐詞、江幡孝之、井口佳哉
  • Organizer: 第７回分子科学討論会
  • Place of Presentation: 京都
• [Presentation] レーザー分光実験と量子化学計算によるエストロゲンの水酸基の水素結合能力と生理活性に関する研究 (2013)
  • Author(s): 森島史哉、井口佳哉、江幡孝之
  • Organizer: 第７回分子科学討論会
  • Place of Presentation: 京都
• [Presentation] イオン包接錯体の研究を目的とした極低温レーザー分光装置の開発 (2013)
  • Author(s): 曽我和毅、江幡孝之、井口佳哉
  • Organizer: 第７回分子科学討論会
  • Place of Presentation: 京都
• [Presentation] Nonradiative decay dynamics of p-coumaric acid and its derivatives in the gas phase (2013)
  • Author(s): T. Ebata
  • Organizer: Core-to-core international symposium on ionization induced switching
  • Place of Presentation: マンチェスター、英国
  • Invited
• [Remarks] 広島大学大学院理学研究科化学専攻 構造物理化学研究グループ
  • URL: http://home.hiroshima-u.ac.jp/ebatalab/
• [Remarks] 広島大学大学院理学研究科化学専攻 構造物理化学研究グループ
  • URL: http://home.hiroshima-u.ac.jp/ebatalab/