Faculty Profiles - SHINOKUBO, Hiroshi

Papers - SHINOKUBO, Hiroshi

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Pyrrole-Bridged Porphyrin Nanorings Reviewed

Jianxin Song, Naoki Aratani, and Hiroshi Shinokubo, Atsuhiro Osuka

Chem. Eur. J. Vol. 16 ( 45 ) page： 13320-13324 2010.11

A Porphyrin Nanobarrel that Encapsulates C60 Reviewed

Jianxin Song, Naoki Aratani, Hiroshi Shinokubo, and Atsuhiro Osuka

J. Am. Chem. Soc. Vol. 132 ( 46 ) page： 16356-16357 2010.10

Platinum(II) and Platinum(IV) Porphyrin Pincer Complexes: Synthesis, Structures, and Reactivity Reviewed International journal

Keita Yoshida, Shigeru Yamaguchi, Atsuhiro Osuka, Hiroshi Shinokubo

ORGANOMETALLICS Vol. 29 ( 17 ) page： 3997 - 4000 2010.9

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：AMER CHEMICAL SOC

Pt(II)and Pt(IV)porphyrin pincer complexes were synthesized and characterized. Their structures and electronic properties were influenced by the valence state of platinum at the outer coordination site. The considerable distortion in the porphyrin core of the Pt(II) complex was relieved in the Pt(IV) complex, due to the change of the coordination geometry of platinum. Oxidation of the phenylplatinum(II) pincer complex with iodine induced a facile carbon carbon bond formation reaction at the meso position via reductive elimination.

DOI： 10.1021/om100644n

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Directly Pd(II)-Bridged Porphyrin Belts with Remarkable Curvatures Reviewed

Jianxin Song, Naoki Aratani, Ji Haeng Heo, Dongho Kim, Hiroshi Shinokubo, and Atsuhiro Osuka

J. Am. Chem. Soc. Vol. 132 ( 34 ) page： 11868-11869 2010.9

eta(2)-Porphyrin Ru(II) pi Complexes Reviewed International journal

Shigeru Yamaguchi, Hiroshi Shinokubo, Atsuhiro Osuka

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY Vol. 132 ( 29 ) page： 9992 - 9993 2010.7

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：AMER CHEMICAL SOC

Highly stable eta(2)-porphyrin Ru(II) pi complexes have been synthesized. The formation of the eta(2) pi it bond has been facilitated through pi-pi stacking interactions between the porphyrin and the planar ligand on Ru. pi coordination of ruthenium to porphyrin results in dramatic changes in the aromaticity and electronic properties. These properties are controllable via fine-tuning of the ligand on ruthenium.

DOI： 10.1021/ja104842h

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A Stable Non-Kekule Singlet Biradicaloid from meso-Free 5,10,20,25-Tetrakis(Pentafluorophenyl)-Substituted [26]Hexaphyrin(1.1.1.1.1.1) Reviewed International journal

Taro Koide, Ko Furukawa, Hiroshi Shinokubo, Jae-Yoon Shin, Kil Suk Kim, Dongho Kim, Atsuhiro Osuka

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY Vol. 132 ( 21 ) page： 7246 - + 2010.6

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：AMER CHEMICAL SOC

A meso,meso-diketohexaphyrin was isolated and characterized as a chemically stable non-Kekule singlet biradicaloid. Two unpaired electrons are seemingly delocalized on two tripyrrolic units separated by C=O bonds. These results underscore the potential of expanded porphyrins to achieve unique electronic states.

DOI： 10.1021/ja101040s

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Synthesis of meso,meso'-Pyrrole-Bridged Diporphyrins by Cu(I)-Mediated Annulation Reviewed

Chihiro Maeda, Hiroshi Shinokubo, and Atsuhiro Osuka

Org. Lett. Vol. 12 ( 8 ) page： 1820-1823 2010.4

Porphyrin "Lego Block" Strategy To Construct Directly meso-beta Doubly Linked Porphyrin Rings Reviewed

Jianxin Song, Naoki Aratani, Pyosang Kim, Dongho Kim, Hiroshi Shinokubo, and Atsuhiro Osuka

Angew. Chem., Int. Ed. Vol. 49 ( 21 ) page： 3617-3620 2010.4

Large Porphyrin Squares from the Self-Assembly of meso-Triazole-Appended L-Shaped meso-meso-Linked ZnII-Triporphyrins: Synthesis and Efficient Energy Transfer Reviewed

Chihiro Maeda, Pyosang Kim, Sung Cho, Jong Kang Park, Jong Min Lim, Dongho Kim, Josh Vura-Weis, Michael R. Wasielewski, and Hiroshi Shinokubo, Atsuhiro Osuka

Chem. Eur. J. Vol. 16 ( 17 ) page： 5052-5061 2010.3

Excess Polarizability Reveals Exciton Localization/Delocalization Controlled by Linking Positions on Porphyrin Rings in Butadiyne-Bridged Porphyrin Dimers Reviewed

Chunxing She, Shanmugam Easwaramoorthi, Pyosang Kim, Satoru Hiroto, Ichiro Hisaki, Hiroshi Shinokubo, Atsuhiro Osuka, Dongho Kim and Joseph T. Hupp

J. Phys. Chem. A Vol. 114 ( 10 ) page： 3384-3390 2010.3

Strategic Synthesis of 2,6-Pyridylene-Bridged β-to-β Porphyrin Nanorings through Cross-Coupling Reviewed

Jianxin Song, Pyosang Kim, Naoki Aratani, Dongho Kim, Hiroshi Shinokubo, and Atsuhiro Osuka

Chem. Eur. J. Vol. 16 ( 10 ) page： 3009-3012 2010.2

Bithiophene-Porphyrin Hybrid Nanorings Reviewed

Kenta Osawa, Jianxin Song, Ko Furukawa, Hiroshi Shinokubo, Naoki Aratani, and Atsuhiro Osuka

Chem. Asian J. Vol. 5 ( 4 ) page： 764-767 2010.1

A Stable Organic Radical Delocalized on a Highly Twisted pi System Formed Upon Palladium Metalation of a Mobius Aromatic Hexaphyrin Reviewed International journal

Harapriya Rath, Sumito Tokuji, Naoki Aratani, Ko Furukawa, Jong Min Lim, Dongho Kim, Hiroshi Shinokubo, Atsuhiro Osuka

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION Vol. 49 ( 8 ) page： 1489 - 1491 2010

Doubly beta-Functionalized Meso-Meso Directly Linked Porphyrin Dimer Sensitizers for Photovoltaics Reviewed International journal

Jong Kang Park, Jinping Chen, Hye Ryun Lee, Sun Woo Park, Hiroshi Shinokubo, Atsuhiro Osuka, Dongho Kim

JOURNAL OF PHYSICAL CHEMISTRY C Vol. 113 ( 52 ) page： 21956 - 21963 2009.12

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：AMER CHEMICAL SOC

Novel meso-meso directly linked porphyrin dinners tethered at beta-pyrrolic positions of the porphyrin ring with 2-propenoic acids or 2,4-pentadienoic acids were prepared for sensitization of nanocrystalline titanium dioxide solar cells. Most importantly, the absorption spectra of dimeric porphyrins were notably extended into the midvisible region in the solar spectrum while the LUMO levels are sufficiently high to inject electrons to the conduction band of TiO2. Among these dimers, PEG-2b-bd-Zn2 dimer, bearing a poly(ethylene glycol) end group at one meso position, showed the highest incident photon-to-photocurrent generation with 47% efficiency at the Soret region as well as the power conversion efficiency of 4.2% under standard AM 1.5 solar condition. To elucidate electronic structures and excited-state properties, UV-vis absorption and emission, cyclic voltammetry measurements, and density functional theory Calculations were performed. To Our best knowledge, the obtained conversion efficiency of 4.2% from PEG-2b-bd-Zn2-sensitized DSSC is the highest photovoltaic performance among DSSCs based on oligomeric porphyrins. Thus, this work suggests that the wide spectral response of directly linked porphyrin dimers due to the excitonic coupling is an intriguing aspect of directly linked pophyrin dimers to be utilized for DSSCs and gives an insight into the design of more efficient light-harvesting molecules.

DOI： 10.1021/jp905675x

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Synthesis of Arylated Perylene Bisimides through C-H Bond Cleavage under Ruthenium Catalysis Reviewed

Satomi Nakazono, Shanmugam Easwaramoorthi, Dongho Kim, Hiroshi Shinokubo, and Atsuhiro Osuka

Org. Lett. Vol. 11 ( 23 ) page： 5426-5429 2009.12

meso,meso '-Bis(5-azaindol-2-yl)-Appended meso-meso-Linked Zn(II) Diporphyrin: A Discrete Fluorescent Assembly Reviewed International journal

Chihiro Maeda, Hiroshi Shinokubo, Atsuhiro Osuka

ORGANIC LETTERS Vol. 11 ( 22 ) page： 5322 - 5325 2009.11

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：AMER CHEMICAL SOC

Cu(II)-catalyzed intramolecular cyclization of meso-(4-aminopyrid-3-yl)ethynyl Zn(II) porphyrin provided meso-(5-azaindol-2-yl)-substituted Zn(II) porphyrin. meso,meso'-Bis(5-azaindol-2-yl)-substituted diporphyrin 7 was similarly prepared and was found to form a fluorescent trimeric prismatic assembly consisting of single atropisomer 7(in-in).

DOI： 10.1021/ol902294r

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Palladium-Catalyzed Dimerization of meso-Bromoporphyrins: Highly Regioselective meso-beta Coupling through Unprecedented Remote C-H Bond Cleavage Reviewed International journal

Sumito Tokuji, Taiga Yurino, Naoki Aratani, Hiroshi Shinokubo, Atsuhiro Osuka

CHEMISTRY-A EUROPEAN JOURNAL Vol. 15 ( 45 ) page： 12208 - 12211 2009.10

Regioselective Ru-Catalyzed Direct 2,5,8,11-Alkylation of Perylene Bisimides Reviewed

Satomi Nakazono, Yusuke Imazaki, Hyejin Yoo, Jaesung Yang, Takahiro Sasamori, Norihiro Tokitoh, Tassel Cédric, Hiroshi Kageyama, Dongho Kim, Hiroshi Shinokubo, and Atsuhiro Osuka

Chem. Eur. J. Vol. 15 ( 31 ) page： 7530-7533 2009.7

Porphyrin Derivatives with Carbon-Metal Bonds Reviewed

Satoru Hiroto, Shigeru Yamaguchi, Hiroshi Shinokubo, and Atsuhiro Osuka

J. Synth. Org. Chem. Jpn. Vol. 67 ( 7 ) page： 688-700 2009.7

Unusual Interchromophoric Interactions in beta,beta ' Directly and Doubly Linked Corrole Dimers: Prohibited Electronic Communication and Abnormal Singlet Ground States Reviewed International journal

Sung Cho, Jong Min Lim, Satoru Hiroto, Pyosang Kim, Hiroshi Shinokubo, Atsuhiro Osuka, Dongho Kim

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY Vol. 131 ( 18 ) page： 6412 - 6420 2009.5

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：AMER CHEMICAL SOC

Directly and doubly beta,beta'-linked corrole dimers (DH3CD, DH2CD, and DZnCD) are excellent platforms for the investigation of intercorrole interactions because of their enforced coplanar geometries and short edge-to-edge distances. Through the use of these molecules along with the reference monomer H3CM and the singly beta,beta'-linked corrole dimer SH3CD, the intercorrole interactions have been systematically studied by density functional theory calculations, ultrafast photophysical measurements, and two-photon absorption measurements. A particular focus was placed on revealing factors that are important for the induced photophysical properties of the doubly linked corrole dimers compared with corrole monomer. In the doubly linked corrole dinners, strong molecular orbital interactions caused by the coplanar geometry and the short interchromophoric distance give rise to perturbations of the electronic states that are responsible for the red-shifted and intensified Q-like band in DH3CD and the broad NIR absorption bands and fast excitation-energy relaxation processes in DH2CD and DZnCD. On the other hand, electronic communication between corrole units is prohibited by the structurally constrained octagonal core in the center, so each constituent corrole unit in the doubly linked corrole dimers maintains an intrinsic pi-conjugation system. Consequently, the overall aromaticity of the directly linked corrole dimers can be explained in terms of a linear sum of two constituent corrole monomers, and the singlet biradical character of DH2CD and DZnCD can be understood in terms of two unpaired electrons (one from each constituent oxidized corrole monomer) and their appropriate interaction. In addition, the nonlinear optical properties of DH2CD and DZnCD with singlet biradical character have been confirmed to be significantly enhanced compared with those of closed-shell DH3CD. Collectively, double beta,beta'-linkages of corroles provide the coplanar geometry with a short interchromophoric distance and the strained octagonal core that play key roles in allowing the strong molecular orbital interactions and restricting the electronic communication between the two corroles, respectively.

DOI： 10.1021/ja900220y

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Papers - SHINOKUBO, Hiroshi