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Pure Appl. Chem., 1990, Vol. 62, No. 8, pp. 1511-1520

http://dx.doi.org/10.1351/pac199062081511

A chemical approach toward photosynthetic reaction center

K. Maruyama and A. Osuka

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  • Mikhalitsyna Elena A., Tyurin Vladimir S., Zamylatskov Ilia A., Khrustalev Victor N., Beletskaya Irina P.: Synthesis, characterization and cation-induced dimerization of new aza-crown ether-appended metalloporphyrins. Dalton Trans. 2012, 41, 7624. <http://dx.doi.org/10.1039/c2dt30123g>
  • Takagi Shinsuke, Aratake Yoshito, Konno Saki, Masui Dai, Shimada Tetsuya, Tachibana Hiroshi, Inoue Haruo: Effects of porphyrin structure on the complex formation behavior with clay. Microp Mesop Mat 2011, 141, 38. <http://dx.doi.org/10.1016/j.micromeso.2009.11.011>
  • Osuka Atsuhiro, Tsurumaki Eiji, Tanaka Takayuki: Subporphyrins: A Legitimate Ring-Contracted Porphyrin with Versatile Electronic and Optical Properties. Bull Soc Jpn 2011, 84, 679. <http://dx.doi.org/10.1246/bcsj.20110118>
  • Kojima Takahiko, Hanabusa Kakeru, Ohkubo Kei, Shiro Motoo, Fukuzumi Shunichi: Construction of SnIV Porphyrin/Trinuclear Ruthenium Cluster Dyads Linked by Pyridine Carboxylates: Photoinduced Electron Transfer in the Marcus Inverted Region. Chem Eur J 2010, 16, 3646. <http://dx.doi.org/10.1002/chem.200902939>
  • El-Khouly Mohamed E., Han Ki-Jong, Kay Kwang-Yol, Fukuzumi Shunichi: Stabilization of the Charge-Separated States of Covalently Linked Zinc Porphyrin-Triphenylamine-[60]Fullerene. chem phys chem 2010, 11, 1726. <http://dx.doi.org/10.1002/cphc.200900885>
  • Song Hee-eun, Taniguchi Masahiko, Kirmaier Christine, Bocian David F., Lindsey Jonathan S., Holten Dewey: Probing Ground-state Hole Transfer Between Equivalent, Electrochemically Inaccessible States in Multiporphyrin Arrays Using Time-resolved Optical Spectroscopy. Photchem Photbio 2009, 85, 693. <http://dx.doi.org/10.1111/j.1751-1097.2008.00471.x>
  • Xu Wei, Chen Hailong, Wang Yanfeng, Zhao Chuntao, Li Xiyou, Wang Shuangqing, Weng Yuxiang: Photoinduced Electron and Energy Transfer in Dyads of Porphyrin Dimer and Perylene Tetracarboxylic Diimide. Chem Eur J of Chem Phys 2008, 9, 1409. <http://dx.doi.org/10.1002/cphc.200800028>
  • Oswald Frédéric, Islam D.-M. Shafiqul, Araki Yasuyuki, Troiani Vincent, de la Cruz Pilar, Moreno Andrés, Ito Osamu, Langa Fernando: Synthesis and Photoinduced Intramolecular Processes of Fulleropyrrolidine–Oligothienylenevinylene–Ferrocene Triads. Chem Eur J 2007, 13, 3924. <http://dx.doi.org/10.1002/chem.200601889>
  • Takagi Akihiko, Hori Takaaki, Peng Xiobin, Aratani Naoki, Matsumoto Takuya, Osuka Atsuhiro, Kawai Tomoji: Discrete dihedral-angle modulation in porphyrin wheels adsorbed on Cu(100) observed by scanning tunneling microscopy. Surf Sei 2007, 601, 2178. <http://dx.doi.org/10.1016/j.susc.2007.03.012>
  • Jiu Tonggang, Li Yongjun, Gan Haiyang, Li Yuliang, Liu Huibiao, Wang Shu, Zhou Weidong, Wang Chunru, Li Xiaofang, Liu Xiaofeng, Zhu Daoben: Synthesis of oligo(p-phenylene vinylene)-porphyrin-oligo(p-phenylene vinylene) triads as antenna molecules for energy transfer. Tetrahedron 2007, 63, 232. <http://dx.doi.org/10.1016/j.tet.2006.10.029>
  • Yamanaka Ken-ichi, Fujitsuka Mamoru, Araki Yasuyuki, Tashiro Kentaro, Sato Azumi, Yuzawa Tetsuro, Aida Takuzo: Intramolecular photoinduced electron-transfer processes in buta-1,3-diynyl-benzene-linked porphyrin-fullerene dyad. J. Porphyrins Phthalocyanines 2007, 11, 397. <http://dx.doi.org/10.1142/S108842460700045X>
  • Marek Diane, Narra Muralikrishna, Schneider Aaron, Swavey Shawn: Synthesis, characterization and electrode adsorption studies of porphyrins coordinated to ruthenium(II) polypyridyl complexes. Inorg Chim Ada 2006, 359, 789. <http://dx.doi.org/10.1016/j.ica.2005.04.037>
  • Jahan Maryam, Safari Nasser, Khosravi Hengameh, Moghimi Abolghasem, Notash Behrouz: Crown ether-appended porphyrins and metalloporphyrins: Synthesis, characterization and metal ions interaction. J Polyhedron 2005, 24, 1682. <http://dx.doi.org/10.1016/j.poly.2005.04.033>
  • El-Khouly Mohamed E., Rogers Lisa M., Zandler Melvin E., Suresh Gadde, Fujitsuka Mamoru, Ito Osamu, D'Souza Francis: Studies on Intra-Supramolecular and Intermolecular Electron-Transfer Processes between Zinc Naphthalocyanine and Imidazole-Appended Fullerene. Chem Eur J of Chem Phys 2003, 4, 474. <http://dx.doi.org/10.1002/cphc.200200540>
  • Aratani Naoki, Osuka Atsuhiro: Directly linked porphyrin arrays. Chem Record 2003, 3, 225. <http://dx.doi.org/10.1002/tcr.10062>
  • Liu Xiao-Juan, Feng Ji-Kang, Ren Ai-Min, Zhou Xin: Comparative studies of the spectra and the second-order nonlinear polarizabilities for donor���acceptor ensembles between Zn-porphyrin/fullerene [60] and Zn-porphyrin/naphthalenediimide. Journal of Molecular Structure: THEOCHEM 2003, 635, 191. <http://dx.doi.org/10.1016/S0166-1280(03)00420-2>
  • Shinmori Hideyuki, Yasuda Yuzo, Osuka Atsuhiro: Control ofFace-to-face and Extended Aggregations of Crown Ether-Appended Metalloporphyrins. Eur J Org Chem 2002, 2002, 1197. <http://dx.doi.org/10.1002/1099-0690(200204)2002:7<1197::AID-EJOC1197>3.0.CO;2-J>
  • Shinmori Hideyuki, Furuta Hiroyuki, Osuka Atsuhiro: Effective face-to-face dimerization of a crown ether appended N-confused porphyrin. Tetrahetron Lett 2002, 43, 4881. <http://dx.doi.org/10.1016/S0040-4039(02)00832-8>
  • Aratani Naoki, Osuka Atsuhiro, Cho Hyun Sun, Kim Dongho: Photochemistry of covalently-linked multi-porphyrinic systems. J Photochem Photobiol C Photochem Rev 2002, 3, 25. <http://dx.doi.org/10.1016/S1389-5567(02)00003-5>
  • Shinmori Hideyuki, Kajiwara Takashi, Osuka Atsuhiro: Supramolecular assembly of light harvesting porphyrin hexamer. Tetrahetron Lett 2001, 42, 3617. <http://dx.doi.org/10.1016/S0040-4039(01)00520-2>
  • Aratani Naoki, Osuka Atsuhiro: A New Strategy for Construction of Covalently Linked Giant Porphyrin Arrays with One, Two, and Three Dimensionally Arranged Architectures. Bull Chem Soc Jpn 2001, 74, 1361. <http://dx.doi.org/10.1246/bcsj.74.1361>
  • Puranen E.-L, Stapelbroek-Möllmann M.E, Vuorimaa E, Tkachenko N, Tauber A.Y, Hynninen P.H, Lemmetyinen H: Photophysical studies of 1,4-diazabicyclo(2,2,2)octane as a bifunctional ligand to fix the conformation of a flexibly-linked phorbinato-zinc dimer. J Photochem Photobiol A Chem 2000, 136, 179. <http://dx.doi.org/10.1016/S1010-6030(00)00346-4>
  • Zhao Feng, Zhang Jian, Abe Toshiyuki, Wöhrle Dieter, Kaneko Masao: Electrocatalytic proton reduction by phthalocyanine cobalt derivatives incorporated in poly(4-vinylpyridine-co-styrene) film. Journal of Molecular Catalysis A 1999, 145, 245. <http://dx.doi.org/10.1016/S1381-1169(99)00013-8>
  • Ren Qi-Zhi, Huang Jin-Wang, Peng Xiao-Bin, Ji Liang-Nian: Hydroxylation of cyclohexane catalyzed by iron(III)–iron(III) porphyrin dimers and DABCO with molecular oxygen: evidence for the conformation effect of porphyrin dimers on the catalytic activity. Journal of Molecular Catalysis A 1999, 148, 9. <http://dx.doi.org/10.1016/S1381-1169(99)00038-2>
  • Zhao Feng, Zhang Jian, Kaneko Masao: Specific emission and quenching of photoexcited tetraphenylporphyrin derivatives incorporated in a Nafion film. J Photochem Photobiol A Chem 1998, 119, 53. <http://dx.doi.org/10.1016/S1010-6030(98)00383-9>
  • Shinoda Satoshi, Tsukube Hiroshi, Nishimura Yoshinobu, Yamazaki Iwao, Osuka Atsuhiro: Energy and electron transfer properties of methyl pheophorbide-a in zinc porphyrin-pheophorbide dyads. Tetrahedron 1997, 53, 13657. <http://dx.doi.org/10.1016/S0040-4020(97)00902-2>
  • Katoh Takashi, Inagaki Yoshio, Okazaki Renji: Linear and Stack Oligostreptocyanines. Effects of Relative Orientation of Chromophores on Redox Potentials of Dye Aggregates. Bull Chem Soc Jpn 1997, 70, 2279. <http://dx.doi.org/10.1246/bcsj.70.2279>
  • Osuka Atsuhiro, Yamada Hiroko, Shinoda Satoshi, Nozaki Koichi, Ohno Takeshi: Intramolecular charge recombination in carotenoid—porphyrin—pyromellitimide triads. chem phys letts 1995, 238, 37. <http://dx.doi.org/10.1016/0009-2614(95)00363-0>
  • Osuka Atsuhiro, Marumo Shinji, Maruyama Kazuhiro, Mataga Noboru, Tanaka Yoshinori, Taniguchi Seiji, Okada Tadashi, Yamazaki Iwao, Nishimura Yoshinobu: Sequential Electron Transfer Leading to Long-Lived Charge Separated State in a Porphyrin-Oxochlorin-Pyromellitdimide Triad. Bull Chem Soc Jpn 1995, 68, 262. <http://dx.doi.org/10.1246/bcsj.68.262>
  • Osuka Atsuhiro, Marumo Shinji, Wada Yukihisa, Yamazaki Iwao, Yamazaki Tomoko, Shirakawa Yoshihiro, Nishimura Yoshinobu: Synthesis of 1,3-Dioxane-Bridged Pyropheophorbide-Diimide and Pyropheophorbide Dimer and Their Intramolecular Electron and Energy Transfer. Bull Chem Soc Jpn 1995, 68, 2909. <http://dx.doi.org/10.1246/bcsj.68.2909>
  • Marumo Shinji, Maruyama Kazuhiro, Mataga Noboru, Ohkochi Masaya, Taniguchi Seiji, Okada Tadashi, Yamazaki Iwao, Nishimura Yoshinobu, Osuka Atsuhiro: Picosecond excited-state dynamics of fixed-distance triads consisting of metalloporphyrin, doubly strapped metal-free porphyrin, and pyromellitimide. chem phys letts 1994, 225, 140. <http://dx.doi.org/10.1016/0009-2614(94)00628-8>
  • Marumo Shinji, Taniguchi Seiji, Osuka Atsuhiro, Okada Tadashi, Mataga Noboru: Electron transfer over two porphyrins in linear porphyrin arrays. chem phys letts 1994, 230, 144. <http://dx.doi.org/10.1016/0009-2614(94)01122-2>
  • Banfi Stefano, Montanari Fernando, Pozzi Gianluca, Quici Silvio: Dimeric Mn(III)-tetraarylporphyrins as catalysts for H2O2-promoted olefin epoxidation. Tetrahedron 1994, 50, 9025. <http://dx.doi.org/10.1016/S0040-4020(01)85369-2>
  • Pöllinger F., Heitele H., Michel-Beyerle M.E., Tercel M., Staab H.A.: Stacked porphyrin—quinone triads as models for the primary charge-separation in photosynthesis. chem phys letts 1993, 209, 251. <http://dx.doi.org/10.1016/0009-2614(93)80103-V>
  • Gribkova S E, Evstigneeva Rima P, Luzgina Valentina N: Synthesis of molecular complexes based on porphyrins for the investigation of the energy transfer and primary charge separation in photosynthesis. RUSS CHEM REV 1993, 62, 963. <http://dx.doi.org/10.1070/RC1993v062n10ABEH000057>
  • Osuka Atsuhiro, Zhang Run-Ping, Maruyama Kazuhiro, Ohno Takeshi, Nozaki Koichi: Synthesis and Intramolecular Charge Separation of Fixed-Distance Triads Consisting of Zinc Porphyrin, Metal-Free Porphyrin, and Electron-Accepting Diimide Moiety. Bull Chem Soc Jpn 1993, 66, 3773. <http://dx.doi.org/10.1246/bcsj.66.3773>
  • Osuka Atsuhiro, Marumo Shinji, Maruyama Kazuhiro: Synthesis of 5,15-Diaryl-Substituted Oxochlorins from 5,15-Diaryloctaethylporphyrin. Bull Chem Soc Jpn 1993, 66, 3837. <http://dx.doi.org/10.1246/bcsj.66.3837>
  • Osuka Atsuhiro, Zhang Run-Ping, Maruyama Kazuhiro, Ohno Takeshi, Nozaki Koichi: Long-lived Charge Separated States from Zinc Porphyrin-Free Base Porphyrin-Diimide-Quinone Tetrads. Chem Lett 1993, 1727. <http://dx.doi.org/10.1246/cl.1993.1727>
  • Osuka Atsuhiro, Marumo Shinji, Konishi Norifumi, Maruyama Kazuhiro, Yamazaki Iwao, Yamazaki Tomoko, Shirakawa Yoshihiro, Nishimura Yoshinobu: 1,3-Dioxane-Bridged Pyromellitimide-Pyropheophorbide and Pyropheophorbide Dimer. Chem Lett 1993, 2141. <http://dx.doi.org/10.1246/cl.1993.2141>
  • Osuka Atsuhiro, Nagata Toshi, Kobayashi Fumikazu, Ping Zhang Run, Maruyama Kazuhiro, Mataga Noboru, Asahi Tsuyoshi, Ohno Takeshi, Nozaki Koichi: Long-lived charge separated states from distance fixed triads consisting of zinc porphyrin, free-base porphyrin, and pyromellitimide. chem phys letts 1992, 199, 302. <http://dx.doi.org/10.1016/0009-2614(92)80122-R>
  • Osuka Atsuhiro, Zhang Run Ping, Maruyama Kazuhiro, Yamazaki Iwao, Nishimura Yoshinobu: Synthesis and Intramolecular Electron-Transfer Reaction of Distance-Fixed Quinone-Linked Porphyrins. Bull Chem Soc Jpn 1992, 65, 2807. <http://dx.doi.org/10.1246/bcsj.65.2807>
  • Osuka Atsuhiro, Ikawa Yoshiya, Maruyama Kazuhiro: Synthesis of Benzochlorin Monomer, Dimer, and Porphyrin-Benzochlorin Heterodimer from 5-Aryl- and 5,15-Diaryl-octaethylporphyrins. Bull Chem Soc Jpn 1992, 65, 3322. <http://dx.doi.org/10.1246/bcsj.65.3322>
  • Nagata Toshi: Synthesis and Characterization of Doubly-Strapped Porphyrins. Bull Chem Soc Jpn 1992, 65, 385. <http://dx.doi.org/10.1246/bcsj.65.385>
  • Osuka Atsuhiro, Nagata Toshi, Maruyama Kazuhiro, Mataga Noboru, Asahi Tsuyoshi, Yamazaki Iwao, Nishimura Yoshinobu: Intramolecular photoinduced electron transfer in fixed distance triads consisting of free-base porphyrin, zinc porphyrin, and electron acceptor. chem phys letts 1991, 185, 88. <http://dx.doi.org/10.1016/0009-2614(91)80145-N>
  • Osuka Atsuhiro, Nakajma Satoshi, Maruyama Kazuhiro, Mataga Noboru, Asahi Tsuyoshi: Intramolecular Photoinduced Electron Transfer in Pyromellitimide-linked Porphyrins. Chem Lett 1991, 1003. <http://dx.doi.org/10.1246/cl.1991.1003>
  • Osuka Atsuhiro, Nagata Toshi, Maruyama Kazuhiro: Doubly-Strapped Porphyrins as Useful Building Blocks for Selectively Metallated Oligoporphyrins. Chem Lett 1991, 1687. <http://dx.doi.org/10.1246/cl.1991.1687>
  • Osuka Atsuhiro, Nagata Toshi, Maruyama Kazuhiro: Synthesis of quinone-linked porphyrin dimer, trimer, and tetramer as models for photosynthetic reaction center. Chem Lett 1991, 481. <http://dx.doi.org/10.1246/cl.1991.481>