研究者詳細 - 忍久保　洋

論文 - 忍久保　洋

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Facile Synthesis of Nitrogen-containing Polycyclic Aromatic Hydrocarbons from Perylene Bisimides 査読有り国際誌

Ito Satoru, Hiroto Satoru, Shinokubo Hiroshi

CHEMISTRY LETTERS 43 巻 ( 8 ) 頁： 1309 - 1311 2014年8月

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：公益社団法人日本化学会

We have developed a facile procedure for the synthesis of π-extended fluorubins from perylene bisimides. Iridium-catalyzed direct borylation, the Suzuki–Miyaura cross-coupling, and an acid-condensation sequence afforded π-extended fluorubins <b>1</b> in moderate yields. X-ray diffraction analysis revealed a planar structure of <b>1</b>. In addition, optical analysis and DFT calculations indicated the presence of intramolecular charge-transfer interactions in <b>1c</b>.

DOI： 10.1246/cl.140330

Synthesis of Diazo-Bridged BODIPY Dimer and Tetramer by Oxidative Coupling of beta-Amino-Substituted BODIPYs 査読有り国際誌

Yokoi Hiroki, Hiroto Satoru, Shinokubo Hiroshi

ORGANIC LETTERS 16 巻 ( 11 ) 頁： 3004 - 3007 2014年6月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Organic Letters

A diazo-bridged BODIPY dimer and tetramer were prepared by the oxidative coupling reaction of β-amino-substituted BODIPYs. The structure of the dimer was elucidated by X-ray diffraction analysis, showing its coplanar orientation of two BODIPY units. Effective extension of π-conjugation was confirmed by optical and electrochemical investigations. © 2014 American Chemical Society.

DOI： 10.1021/ol501131j

Photodynamics of [26]- and [28]Hexaphyrin-Bodipy Hybrids 査読有り国際誌

Shin Ji-Young, Kim Kilsuk, Lim Jong Min, Tanaka Takayuki, Kim Dongho, Kim Kimoon, Shinokubo Hiroshi, Osuka Atsuhiro

CHEMISTRY-A EUROPEAN JOURNAL 20 巻 ( 16 ) 頁： 4574 - 4582 2014年4月

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：Chemistry - A European Journal

A set of hybrids having gradual variation in distances between hexaphyrin and bodipy moieties, given by uses of phenylene, biphenylene, and triphenyelene bridges was prepared. Efficient PET processes from bodipy (donor) to [26]- or [28]hexaphyrin (acceptor) were successfully observed, where the PET speed was controlled by intramolecular distances between the donor and the acceptor. UV irradiation at 515 nm raised a band corresponding to the bodipy absorption. As the time delayed, the bodipy bands decreased and new absorption bands at 615 and 580 nm corresponding to respective absorption bands of [28]- and [26]-hybrids gradually appeared. Whereas the femtosecond transient absorption spectra of [28]/[26]-hybrids having terphenylene bridges completely showed energy transfers from bodipy to hexaphyrin, irradiation of the hybrids using 615 and 580 nm pulses did not induce opposite ways of the PET process. On the basis of enlarged center-to-center-distances of [26]-hybrids than those of [28]-hybrids, the set of [26]-hybrids resulted in slow decay/rise processes. PET parameters obtained with the experiments were fairly consistent with the PET parameters calculated. Speed control: A set of hybrids having gradual variation in distances between hexaphyrin and bodipy moieties was prepared (see figure). Efficient PET processes from bodipy to [26]/[28]hexaphyrin were successfully observed on terphenylene-containing hybrids. [26]-Hybrids performed slower speeds of decay/rise processes than [28]-hybrids on the basis of enlarged center-to-center distances. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

DOI： 10.1002/chem.201400315

Silylethynyl Substituents as Porphyrin Protecting Groups for Solubilization and Selectivity Control 査読有り国際誌

Oda Kazuma, Akita Masanari, Hiroto Satoru, Shinokubo Hiroshi

ORGANIC LETTERS 16 巻 ( 6 ) 頁： 1818 - 1821 2014年3月

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Organic Letters

Silylethynyl substituents are proposed as protecting groups for porphyrin derivatives to enhance their solubility and enable regioselective functionalization. After usage as protecting groups, silylethynyl groups at the meso-positions can be efficiently removed upon heating with aqueous H 2SO4 in the presence of a surfactant. This approach was applied to the preparation of unsymmetrically β-substituted porphyrins and porphin-porphyrin oligomers, which were inaccessible by conventional methods. © 2014 American Chemical Society.

DOI： 10.1021/ol500569b

An Antiaromatic Electrode-Active Material Enabling High Capacity and Stable Performance of Rechargeable Batteries 査読有り国際誌

Shin Ji-Young, Yamada Tetsuya, Yoshikawa Hirofumi, Awaga Kunio, Shinokubo Hiroshi

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 53 巻 ( 12 ) 頁： 3096 - 3101 2014年3月

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：Angewandte Chemie - International Edition

Although aromatic compounds occupy a central position in organic chemistry, antiaromatic compounds have demonstrated little practical utility. Herein we report the application of an antiaromatic compound as an electrode-active material in rechargeable batteries. The performance of dimesityl-substituted norcorrole nickel(II) complex (NiNC) as a cathode-active material was examined with a Li metal anode. A maximum discharge capacity of about 207 mAhg -1 was maintained after 100 charge/discharge cycles. Moreover, the bipolar redox property of NiNC enables the construction of a Li metal free rechargeable battery. The high performance of NiNC batteries demonstrates a prospective feature of stable antiaromatic compounds as electrode-active materials. The balance of power: A discharge capacity of greater than 200 mA h g-1 over 100 charge/discharge cycles was found for a rechargeable battery with an antiaromatic norcorrole NiII complex (NiNC) as a cathode-active material and a Li metal anode. The bipolar redox property of NiNC also enabled the construction of a Li metal free rechargeable battery with high discharge capacity (see scheme) and good cycle performance. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

DOI： 10.1002/anie.201310374

Synthesis of Novel Porphyrinoids through Organometallic Means 査読有り国際誌

Shinokubo Hiroshi

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 72 巻 ( 2 ) 頁： 149 - 157 2014年2月

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：公益社団法人有機合成化学協会

Porphyrin is a representative functional molecule, which consists of four pyrrole units linked by four carbon atoms with an 18/r aromatic character. Most of porphyrin syntheses rely on acid- catalyzed condensation of pyrrole with aldehydes followed by oxidation, which are low-yielding in many cases. To establish more effective porphyrin synthesis, we have devoted our effort to combine porphyrin chemistry and modern organic synthesis through transition metal-mediated reactions. In this article, we focus on synthesis of novel porphyrin analogues through coupling of dipyrrin precursors. The metal-templated strategy using dipyrrin metal complexes was found to be quite efficient to construct porphyrin-like cyclic π-conjugated systems consisting of the dipyrrin unit, which exhibit intriguing optical and electronic properties.

DOI： 10.5059/yukigoseikyokaishi.72.149

有機金属化学的手法による新規ポルフィリン類縁体の合成査読有り国際誌

忍久保洋

有機合成化学協会誌 = Journal of synthetic organic chemistry, Japan 72 巻 ( 2 ) 頁： 149 - 157 2014年2月

Near‐IR Absorbing Nickel(II) Porphyrinoids Prepared by Regioselective Insertion of Silylenes into Antiaromatic Nickel(II) Norcorrole 国際共著国際誌

Takaki Fukuoka, Kenya Uchida, Young Mo Sung, Ji‐Young Shin, Shintaro Ishida, Jong Min Lim, Satoru Hiroto, Ko Furukawa, Dongho Kim, Takeaki Iwamoto, Hiroshi Shinokubo

Angewandte Chemie 126 巻 ( 6 ) 頁： 1532 - 1535 2014年1月

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Wiley

<jats:title>Abstract</jats:title><jats:p>The treatment of an antiaromatic norcorrole Ni<jats:sup>II</jats:sup> complex with a kinetically stabilized silylene provided ring‐expansion products in excellent yields through the highly regio‐ and stereoselective insertion into the β‐β pyrrolic CC bonds. The resultant Ni<jats:sup>II</jats:sup> porphyrinoid monoinsertion product exhibited relatively strong near‐IR absorption bands due to the small HOMO–LUMO gap in spite of the disrupted cyclic π‐conjugation by the silicon atom.</jats:p>

DOI： 10.1002/ange.201309921

Transition metal catalyzed borylation of functional pi-systems 査読有り国際誌

Shinokubo Hiroshi

PROCEEDINGS OF THE JAPAN ACADEMY SERIES B-PHYSICAL AND BIOLOGICAL SCIENCES 90 巻 ( 1 ) 頁： 1 - 11 2014年1月

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：日本学士院

Borylated functional π-systems are useful building blocks to enable efficient synthesis of novel molecular architectures with beautiful structures, intriguing properties and unique functions. Introduction of boronic ester substituents to a variety of extended π-systems can be achieved through either iridium-catalyzed direct C–H borylation or the two-step procedure via electrophilic halogenation followed by palladium-catalyzed borylation. This review article focuses on our recent progress on borylation of large π-conjugated systems such as porphyrins, perylene bisimides, hexabenzocoronenes and dipyrrins.

DOI： 10.2183/pjab.90.1

Synthesis, reactivity and property of 5,15-dithiaporphyrin copper(II) complex 査読有り国際誌

Wachi Naruhiko, Kondo Takeshi, Ito Satoru, Hiroto Satoru, Shin Ji-Young, Shinokubo Hiroshi

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES 18 巻 ( 8-9 ) 頁： 675 - 678 2014年

記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Journal of Porphyrins and Phthalocyanines

Preparation of 5,15-dithiaporphyrin copper(II) complex was carried out by treatment of 5,15-dithiaporphyrin free-base with copper(II) acetate. X-ray diffraction analysis elucidated its dimeric structure in the solid state, in which the meso-sulfur atom served as an axial ligand to each pentacoordinated Cu(II) center. Temperature dependent magnetic susceptibility of the complex was measured to reveal the weak antiferromagnetic interaction between two Cu(II) centers in the solid state. 5,15-dithiaporphyrin Cu(II) complex was converted into 10-thiacorrole Cu(II) complex in good yield upon heating with triphenylphosphine in refluxing toluene.

DOI： 10.1142/S1088424614500412

Oxidation of 2-amino-substituted BODIPYs providing pyrazine-fused BODIPY trimers 査読有り国際誌

Yokoi Hiroki, Wachi Naruhiko, Hiroto Satoru, Shinokubo Hiroshi

CHEMICAL COMMUNICATIONS 50 巻 ( 21 ) 頁： 2715 - 2717 2014年

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：Chemical Communications

Oxidation of 2-amino-substituted BODIPYs afforded BODIPY trimers in a one-step operation. The trimer consists of a pyrazine-fused BODIPY dimer to which one BODIPY unit is connected through an NH linkage. Effective expansion of π-conjugation over the fused dimer was observed in optical and electrochemical measurements. © 2014 Royal Society of Chemistry.

DOI： 10.1039/c3cc48738e

Selective Synthesis of a [32]Octaphyrin(1.0.1.0.1.0.1.0) Bis(palladium) Complex by a Metal-Templated Strategy 査読有り国際誌

Kido Hiromitsu, Shin Ji-Young, Shinokubo Hiroshi

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 52 巻 ( 51 ) 頁： 13727 - 13730 2013年12月

Selective Synthesis of a [32]Octaphyrin(1.0.1.0.1.0.1.0) Bis(palladium) Complex by a Metal‐Templated Strategy 国際誌

Hiromitsu Kido, Ji‐Young Shin, Hiroshi Shinokubo

Angewandte Chemie 125 巻 ( 51 ) 頁： 13972 - 13975 2013年10月

担当区分：責任著者記述言語：英語掲載種別：研究論文（学術雑誌）出版者・発行元：Wiley

A shapely figure: A [32]octaphyrin(1.0.1.0.1.0.1.0) bis[palladium(II)] complex was selectively obtained through a metal-templated intermolecular homocoupling of a α,α'-dibromodipyrrin palladium(II) complex without formation the norcorrole. The weak antiaromatic character of the figure-eight [32]octaphyrin(1.0.1.0.1.0.1.0) system has been elucidated by spectroscopic measurements and DFT calculations.

DOI： 10.1002/ange.201306905

Synthesis of Pyridine-Fused Perylene Imides with an Amidine Moiety for Hydrogen Bonding 査読有り国際誌

Ito Satoru, Hiroto Satoru, Shinokubo Hiroshi

ORGANIC LETTERS 15 巻 ( 12 ) 頁： 3110 - 3113 2013年6月

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：American Chemical Society (ACS)

Pyridine-fused perylene tetracarboxylic acid bisimides (PBIs) were synthesized via Suzuki-Miyaura coupling and acid condensation. The fused PBIs with electron-donating substituents exhibited an intramolecular charge transfer interaction. One of the N-alkyl substituents was selectively removed with BBr3 to create an amidine guest binding site. A hydrogen bonding interaction with pentafluorobenzoic acid changed the absorption spectra and enhanced fluorescence. © 2013 American Chemical Society.

DOI： 10.1021/ol401316q

Porphyrin Analogues That Consist of Indole, Benzofuran, and Benzothiophene Subunits 査読有り国際誌

Nakamura Shoichi, Kondo Takeshi, Hiroto Satoru, Shinokubo Hiroshi

ASIAN JOURNAL OF ORGANIC CHEMISTRY 2 巻 ( 4 ) 頁： 312 - 319 2013年4月

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：Asian Journal of Organic Chemistry

We have designed and synthesized porphyrin analogues that consist of benzofuran, benzothiophene, and indole subunits through iridium-catalyzed CH borylation of bisbenzoheterole precursors and subsequent palladium-catalyzed cross-couplings. In the case of the benzofuran derivatives, a cyclic hexamer was also obtained. The cyclic benzoheterole tetramers were more stable in air than the corresponding cyclic tetraindole. X-ray crystallography revealed that the benzoheterole tetramers have more planar conformations than the cyclic tetraindole. Compared with the cyclic tetraindole, the lowest energy bands in the absorption spectra of the cyclic benzoheteroles are red-shifted, which shows the effective expansion of π-conjugation. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

DOI： 10.1002/ajoc.201300033

Functionalization of Hexa-peri-hexabenzocoronenes: Investigation of the Substituent Effects on a Superbenzene 査読有り国際誌

Yamaguchi Ryuichi, Ito Satoru, Lee Byung Sun, Hiroto Satoru, Kim Dongho, Shinokubo Hiroshi

CHEMISTRY-AN ASIAN JOURNAL 8 巻 ( 1 ) 頁： 178 - 190 2013年1月

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：Chemistry - An Asian Journal

We have demonstrated that the iridium-catalyzed direct borylation of hexa-peri-hexabenzocoronene (HBC) enables regioselective introduction of boryl groups to the para-, ortho-, and meta-substituted HBCs in high yields. The boryl groups have been transformed into various functionalities such as hydroxy, cyano, ethynyl, and amino groups. We have elucidated that the substituents significantly influence the photophysical properties of HBCs to enhance fluorescence quantum yields. DFT calculations revealed that the origin of the substituent effect is the lift in degeneracy in the frontier orbitals by an interaction with electron-donating and electron-withdrawing substituents at the para- and ortho-positions. The change in molecular orbitals results in an increase of the transition probability from the S0→S1 states. In addition, the two-photon absorption cross-section values of para-substituted HBCs are significantly larger than those of ortho- and meta-substituted HBCs. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

DOI： 10.1002/asia.201200723

Synthesis of Highly Distorted pi-Extended [2.2]Metacyclophanes by Intermolecular Double Oxidative Coupling 査読有り国際誌

Koyama Yutaro, Hiroto Satoru, Shinokubo Hiroshi

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 52 巻 ( 22 ) 頁： 5740 - 5743 2013年

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：Angewandte Chemie - International Edition

A strained relationship: Oxidation of dihydroxy-substituted acenes provides face-to-face [2.2]metacyclophane-like dimers (see scheme; Ored, Si of iPr 3Si groupsblue). The products exhibited highly distorted structures caused by steric repulsion. UV/Vis and electrochemical analysis revealed that the HOMO-LUMO gap was decreased upon dimerization. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

DOI： 10.1002/anie.201301180

Carbolithiation of meso-aryl-substituted 5,15-diazaporphyrin selectively provides 3-alkylated diazachlorins 査読有り国際誌

Yamaji Ayaka, Hiroto Satoru, Shin Ji-Young, Shinokubo Hiroshi

CHEMICAL COMMUNICATIONS 49 巻 ( 44 ) 頁： 5064 - 5066 2013年

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：Chemical Communications

Treatment of meso-mesityl 5,15-diazaporphyrin with alkyllithiums in toluene at low temperature provided monoalkylated diazachlorins through highly regioselective nucleophilic addition at the β-position near the meso-nitrogen atom. © 2013 The Royal Society of Chemistry.

DOI： 10.1039/c3cc41907j

Assembled structures of dipyrrins and their oligomers bridged by dioxy-boron moieties 査読有り国際誌

Maeda Hiromitsu, Nishimura Yuki, Hiroto Satoru, Shinokubo Hiroshi

DALTON TRANSACTIONS 42 巻 ( 45 ) 頁： 15885 - 15888 2013年

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：Dalton Transactions

A linear arrangement of BODIPY dimers and trimers was transformed into boron-bridged box, ladder and cage structures on treatment with spacer units possessing multiple diol moieties. © 2013 The Royal Society of Chemistry.

DOI： 10.1039/c3dt50783a

meso-Thiaporphyrinoids Revisited: Missing of Sulfur by Small Metals 査読有り国際誌

Kamiya Hiroki, Kondo Takeshi, Sakida Takafumi, Yamaguchi Shigeru, Shinokubo Hiroshi

CHEMISTRY-A EUROPEAN JOURNAL 18 巻 ( 50 ) 頁： 16129 - 16135 2012年12月

記述言語：日本語掲載種別：研究論文（学術雑誌）出版者・発行元：Chemistry - A European Journal

Facile synthesis of meso-aryl-substituted 5,15-dithiaporphyrins and 10-thiacorroles has been achieved by sulfidation of α,α'- dichlorodipyrrin metal complexes with sodium sulfide in DMF. Thiacorrole metal complexes exhibit distinct aromaticity due to 18 π-conjugation including the lone pair on sulfur, whereas dithiaporphyrins are nonaromatic judging from 1H NMR spectra, X-ray analysis, and absorption spectra. We have found that NiII and AlIII dithiaporphyrin complexes undergo smooth thermal sulfur extrusion reaction to give the corresponding thiacorrole complexes, whereas free base, ZnII, PdII, and Pt II dithiaporphyrin complexes did not exhibit the similar reactivity. The DFT calculations have elucidated a reaction pathway involving an episulfide intermediate, which can explain the markedly different reactivity among dithiaporphyrin metal complexes. © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

DOI： 10.1002/chem.201203255

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