Yoshinori Yamanoi

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Organization: The University of Tokyo , Japan

Department: Department of Chemistry

Title: Associate Professor(PhD)

TOPICS

Organic Chemistry

Chemicals
References

Access to Chiral Silicon Centers for Application to Circularly Polarized Luminescence Materials

Co-reporter:Shinya Koga, Shuhei Ueki, Masaki Shimada, Ryoma Ishii, Yu Kurihara, Yoshinori Yamanoi, Junpei Yuasa, Tsuyoshi Kawai, Taka-aki Uchida, Munetaka Iwamura, Koichi Nozaki, and Hiroshi Nishihara

The Journal of Organic Chemistry June 16, 2017 Volume 82(Issue 12) pp:6108-6108

Publication Date(Web):May 12, 2017

DOI:10.1021/acs.joc.7b00583

Asymmetric arylation of secondary silanes catalyzed by a Pd-chiral phosphoramidite complex was developed for application to low-molecular-weight circularly polarized luminescence (CPL) materials. The asymmetric arylation provided a convenient, efficient synthetic method for a variety of chiral tertiary silanes (2–21), which were key intermediates for preparing the quaternary silicon center. A stepwise, one-pot procedure was used to transform the appropriate aryl iodide to the quaternary silane (22) with good yield and enantioselectivity. Among compounds synthesized in this work, four optically pure tertiary silanes (18–21) were selected to investigate the relationship between the structure and optical properties. Optically pure (S,S)-21 displayed the highest CPL emission with a high fluorescence quantum yield (glum: +0.008, ΦF: 0.42). This simple molecular design provides new strategies for developing small organic CPL dyes.

Multifunctional Octamethyltetrasila[2.2]cyclophanes: Conformational Variations, Circularly Polarized Luminescence, and Organic Electroluminescence

Co-reporter:Masaki Shimada, Yoshinori Yamanoi, Tatsuhiko Ohto, Song-Toan Pham, Ryo Yamada, Hirokazu Tada, Kenichiro Omoto, Shohei Tashiro, Mitsuhiko Shionoya, Mineyuki Hattori, Keiko Jimura, Shigenobu Hayashi, Hikaru Koike, Munetaka Iwamura, Koichi Nozaki, and Hiroshi Nishihara

Journal of the American Chemical Society August 16, 2017 Volume 139(Issue 32) pp:11214-11214

Publication Date(Web):July 21, 2017

DOI:10.1021/jacs.7b05671

Both symmetrical and unsymmetrical cyclophanes containing disilane units, tetrasila[2.2]cyclophanes 1–9, were synthesized. The syn and anti conformations and the kinetics of inversion between two anti-isomers were investigated by X-ray diffraction and variable-temperature NMR analysis, respectively. The flipping motion of two aromatic rings was affected by the bulkiness of the aromatic moiety (1 vs 6), the phase (solid vs solution), and the inclusion by host molecules (1 vs 1⊂[Ag2L]2+). The photophysical, electrochemical, and structural properties of the compounds were thoroughly investigated. Unsymmetrical tetrasila[2.2]cyclophanes 5–8 displayed blue–green emission arising from intramolecular charge transfer. Compound 6 emitted a brilliant green light in the solid state under 365 nm irradiation and showed a higher fluorescence quantum yield in the solid state (Φ = 0.49) than in solution (Φ = 0.05). We also obtained planar chiral tetrasila[2.2]cyclophane 9, which showed interesting chiroptical properties, such as a circularly polarized luminescence (CPL) with a dissymmetry factor of |glum| = ca. 2 × 10–3 at 500 nm. Moreover, an organic green light-emitting diode that showed a maximum external quantum efficiency (ηext) of ca. 0.4% was fabricated by doping 4,4′-bis(2,2′-diphenylvinyl)-1,1′-biphenyl with 6.

Photocurrent Generation of Reconstituted Photosystem II on a Self-Assembled Gold Film

Co-reporter:Mariko Miyachi, Shu Ikehira, Daiki Nishiori, Yoshinori YamanoiMasato Yamada, Masako Iwai, Tatsuya Tomo, Suleyman I. Allakhverdiev, Hiroshi Nishihara

Langmuir 2017 Volume 33(Issue 6) pp:

Publication Date(Web):January 19, 2017

DOI:10.1021/acs.langmuir.6b03499

Photosystem II (PSII)-modified gold electrodes were prepared by the deposition of PSII reconstituted with platinum nanoparticles (PtNPs) on Au electrodes. PtNPs modified with 1-[15-(3,5,6-trimethyl-1,4-benzoquinone-2-yl)]pentadecyl disulfide ((TMQ(CH2)15S)2) were incorporated into the QB site of PSII isolated from thermophilic cyanobacterium Thermosynechococcus elongatus. The reconstitution was confirmed by QA-reoxidation measurements. PSII reconstituted with PtNPs was deposited and integrated on a Au(111) surface modified with 4,4′-biphenyldithiol. The cross section of the reconstituted PSII film on the Au electrode was investigated by SEM. Absorption spectra showed that the surface coverage of the electrode was about 18 pmol PSII cm–2. A photocurrent density of 15 nAcm–2 at E = +0.10 V (vs Ag/AgCl) was observed under 680 nm irradiation. The photoresponse showed good reversibility under alternating light and dark conditions. Clear photoresponses were not observed in the absence of PSII and molecular wire. These results supported the photocurrent originated from PSII and moved to a gold electrode by light irradiation, which also confirmed conjugation with orientation through the molecular wire.

Fluorescence and phosphorescence of a series of silicon-containing six-membered-ring molecules

Co-reporter:Takayuki Nakashima, Masaki Shimada, Yu Kurihara, Mizuho Tsuchiya, Yoshinori Yamanoi, Eiji Nishibori, Kunihisa Sugimoto, Hiroshi Nishihara

Journal of Organometallic Chemistry 2016 Volume 805() pp:27-33

Publication Date(Web):1 March 2016

DOI:10.1016/j.jorganchem.2015.12.042

•9,10-Dihydro-9,10-disilaanthracenes were synthesized by the reaction of 1,2-bis(dimethylsilyl)arenes with 1,2-diiodoarenes.•Their photophysical properties were investigated by UV–vis absorption, fluorescence and phosphorescence spectroscopies.•Some of the compounds exhibited enhanced luminescence and larger Stokes shift in comparison with the carbon analog.Various silicon-containing six-membered-ring molecules were synthesized by Pd-catalyzed coupling reaction of 1,2-bis(dimethylsilyl)arenes with 1,2-diiodoarenes in moderate yields. Their optical properties were investigated via UV–vis absorption, fluorescence and phosphorescence spectroscopies, which indicated that the σ*–π* conjugated system expanded owing to the silicon atoms. Some of the compounds exhibited enhanced luminescence, larger Stokes shift, and phosphorescence in comparison with 9,9,10,10-tetramethyl-9,10-dihydroanthracene. Density functional theory (DFT) studies were also performed to investigate the photophysical properties of the compounds.

Effective Method for Micro-Patterning Arene-Terminated Monolayers on a Si(111) Electrode

Co-reporter:Yoshinori Yamanoi, Tetsuhiro Kobayashi, Hiroaki Maeda, Mariko Miyachi, Masato Ara, Hirokazu Tada, and Hiroshi Nishihara

Langmuir 2016 Volume 32(Issue 27) pp:6825-6829

Publication Date(Web):June 22, 2016

DOI:10.1021/acs.langmuir.6b01370

Microstructured electrodes are significant to modern electrochemistry. A representative aromatic group, 4-ferrocenylphenyl one, was covalently bound to a micropatterned silicon electrode via the arylation of a hydrogen-terminated silicon(111) surface formed selectively on a Si wafer. Starting from a silicon(100)-on-insulator (SOI) wafer, the aromatic monolayer was attached sequentially by spin-coating a resist, electron beam lithography, Cr/Au deposition, lift-off, anisotropic etching with aqueous KOH solution, and Pd-catalyzed arylation. Cyclic voltammetry (CV) and X-ray photoelectron spectroscopy (XPS) are used to characterize the coupling reaction between 4-ferrocenyl group and silicon substrate, and to confirm performance of the final modified microsized electrode. These data show that this synthetic protocol gives chemically well-defined and robust functionalized monolayers on a silicon semiconducting surface with a small electrode.

Cross-Sectional TEM Analysis of an ITO Surface Coated with Photosystem I and Molecular Wires

Co-reporter:Mariko Miyachi

Journal of Inorganic and Organometallic Polymers and Materials 2016 Volume 26( Issue 6) pp:1309-1312

Publication Date(Web):2016 November

DOI:10.1007/s10904-016-0396-5

Photosystem I (PSI) from Thermosynechococcuselongatus was immobilized on ITO by using vitamin K1 exchange with artificial molecular wires in PSI. A PSI-modified surface was prepared for observation of lateral TEM images to provide an understanding of its interfacial structure. This paper describes the use of an ultramicrotome to prepare ultra-thin (< 20 nm) sections of PSI on ITO substrates. Cross-sectional TEM and energy-dispersive X-ray spectrometry supported that monolayer PSI was attached to the ITO electrode.

Bright Solid-State Emission of Disilane-Bridged DonorAcceptorDonor and AcceptorDonorAcceptor Chromophores

Co-reporter:Masaki Shimada;Mizuho Tsuchiya;Dr. Ryota Sakamoto;Dr. Yoshinori Yamanoi; Eiji Nishibori;Dr. Kunihisa Sugimoto; Hiroshi Nishihara

Angewandte Chemie International Edition 2016 Volume 55( Issue 9) pp:3022-3026

Publication Date(Web):

DOI:10.1002/anie.201509380

Abstract

The development of disilane-bridged donor–acceptor–donor (D-Si-Si-A-Si-Si-D) and acceptor–donor–acceptor (A-Si-Si-D-Si-Si-A) compounds is described. Both types of compound showed strong emission (λ_em=ca. 500 and ca. 400 nm, respectively) in the solid state with high quantum yields (Φ: up to 0.85). Compound 4 exhibited aggregation-induced emission enhancement in solution. X-ray diffraction revealed that the crystal structures of 2, 4, and 12 had no intermolecular π–π interactions to suppress the nonradiative transition in the solid state.

Bright Solid-State Emission of Disilane-Bridged DonorAcceptorDonor and AcceptorDonorAcceptor Chromophores

Co-reporter:Masaki Shimada;Mizuho Tsuchiya;Dr. Ryota Sakamoto;Dr. Yoshinori Yamanoi; Eiji Nishibori;Dr. Kunihisa Sugimoto; Hiroshi Nishihara

Angewandte Chemie 2016 Volume 128( Issue 9) pp:3074-3078

Publication Date(Web):

DOI:10.1002/ange.201509380

Abstract

Optical Properties of Disilane-Bridged Donor–Acceptor Architectures: Strong Effect of Substituents on Fluorescence and Nonlinear Optical Properties

Co-reporter:Masaki Shimada; Yoshinori Yamanoi; Tomonori Matsushita; Takashi Kondo; Eiji Nishibori; Akari Hatakeyama; Kunihisa Sugimoto;Hiroshi Nishihara

Journal of the American Chemical Society 2015 Volume 137(Issue 3) pp:1024-1027

Publication Date(Web):January 7, 2015

DOI:10.1021/ja511177e

A series of disilane-bridged donor–acceptor architectures 1–9 containing strong electron-donating and -withdrawing substituents were designed and synthesized in acceptable yields. The substituents substantially affected the fluorescence and nonlinear optical properties of the compounds. In the solid state, the compounds showed purple–blue fluorescence (λem = 360–420 nm) with high quantum yields (up to 0.81). Compound 3, which had p-N,N-dimethylamino and o-cyano substituents, exhibited optical second harmonic generation (activity 2.9 times that of urea, calculated molecular hyperpolarizability β = 1.6 × 10–30 esu) in the powder state. Density functional theory calculations for the ground and excited states indicated that both the locally excited state and the intramolecular charge transfer excited state make important contributions to the luminescence behavior.

Preparation of Pd Nanoparticles with Tetrahedral, Spherical, Plate, and Feather Shapes by Capping with 1-Pentyl Isocyanide

Co-reporter:Mariko Miyachi;Yuki Yamamoto

Journal of Inorganic and Organometallic Polymers and Materials 2015 Volume 25( Issue 1) pp:140-144

Publication Date(Web):2015 January

DOI:10.1007/s10904-014-0121-1

In this study, we synthesized n-alkyl-isocyanide-protected palladium colloidal nanoparticles with different shapes. The 1-pentyl-isocyanide-protected Pd nanoparticles prepared by the reduction of the Pd complex with ethylene glycol had various geometric shapes. Transmission electron micrographs showed that tetrahedral particles were predominant, although some spherical, plate-, and feather-shaped particles were also observed. The enriched nanotetrahedra were isolated as a black powder by reprecipitation with methanol–chloroform and the particle size was controlled by the reaction conditions.

Structures and Optical Properties of Tris(trimethylsilyl)silylated Oligothiophene Derivatives

Co-reporter:Hikaru Inubushi, Yohei Hattori, Yoshinori Yamanoi, and Hiroshi Nishihara

The Journal of Organic Chemistry 2014 Volume 79(Issue 7) pp:2974-2979

Publication Date(Web):March 10, 2014

DOI:10.1021/jo500029f

The structures and optical properties of tris(trimethylsilyl)silylated oligothiophenes were examined by spectroscopies, theoretical calculations, and single-crystal X-ray measurements. Bathochromic shift from the original oligothiophenes was observed in the tris(trimethylsilyl)silylated ones, confirming the σ–π conjugation between Si–Si σ bonds and π-orbital. 5,5′-Bis(tris(trimethylsilyl)silyl)-2,2′-bithiophene (Si-T2) showed the highest fluorescence quantum yield (ΦF) both in solution (0.67, excited at 350 nm) and the solid state (0.74, excited at 371 nm). The introduction of tris(trimethylsilyl)silyl groups led to the small nonradiative rate constant of Si-T2, resulting in the high ΦF in the solution state. Si-T2 also exhibited effective σ–π conjugation and poor molecular interaction, which reflected its high ΦF in the solid state. On the contrary, lower ΦF (0.13, excited at 331 nm) in the solid state was observed in the longest oligothiophene examined, 5,5‴-bis(1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilan-2-yl)-2,2′:5′,2″:5″,2‴-quaterthiophene (Si-T4). Single-crystal X-ray measurement clarified that this compound adopted a zigzag packing structure and a rare syn-anti-syn conformation, which led to the poor σ–π conjugation and the decrease of π-orbital overlap in the solid state.

Pd-catalyzed synthesis of symmetrical and unsymmetrical siloxanes

Co-reporter:Yu Kurihara, Yoshinori Yamanoi and Hiroshi Nishihara

Chemical Communications 2013 vol. 49(Issue 96) pp:11275-11277

Publication Date(Web):10 Oct 2013

DOI:10.1039/C3CC46294C

A palladium-catalyzed arylation of hydrosiloxanes was developed for the synthesis of symmetrical and unsymmetrical siloxanes. Reactive functional moieties such as hydroxy or cyano groups were able to tolerate the reaction conditions and several novel unsymmetrical siloxanes were synthesized in moderate to high yield.

Direct synthesis of alkylsilanes by platinum-catalyzed coupling of hydrosilanes and iodoalkanes

Co-reporter:Hikaru Inubushi, Hitoshi Kondo, Aldes Lesbani, Mariko Miyachi, Yoshinori Yamanoi and Hiroshi Nishihara

Chemical Communications 2013 vol. 49(Issue 2) pp:134-136

Publication Date(Web):16 Oct 2012

DOI:10.1039/C2CC35150A

Alkyl iodides and tertiary silanes were successfully coupled with good functional group tolerance using a Pt(P(tBu)3)2/(iPr)2EtN/CH3CN system. The utility of the methodology is demonstrated by the synthesis of silafluofen, a Si-containing insecticide.

Nanoparticle Assemblies via Coordination with a Tetrakis(terpyridine) Linker Bearing a Rigid Tetrahedral Core

Co-reporter:Yoshinori Yamanoi, Yuki Yamamoto, Mariko Miyachi, Masaki Shimada, Ai Minoda, Shinji Oshima, Yoshihiro Kobori, and Hiroshi Nishihara

Langmuir 2013 Volume 29(Issue 28) pp:8768-8772

Publication Date(Web):2017-2-22

DOI:10.1021/la401896d

Controlling particle–particle interactions is a major challenge in achieving the programmable assembly of nanoparticles, which shows great potential for device fabrication and detection systems. We present here a simple chemical method that allows the formation of Pd nanoparticle assemblies using a tetrakis(terpyridine) linker with a rigid tetrahedral core.

A New Method To Generate Arene-Terminated Si(111) and Ge(111) Surfaces via a Palladium-Catalyzed Arylation Reaction

Co-reporter:Yoshinori Yamanoi ; Junya Sendo ; Tetsuhiro Kobayashi ; Hiroaki Maeda ; Yusuke Yabusaki ; Mariko Miyachi ; Ryota Sakamoto ;Hiroshi Nishihara

Journal of the American Chemical Society 2012 Volume 134(Issue 50) pp:20433-20439

Publication Date(Web):November 26, 2012

DOI:10.1021/ja308606t

Formation of silicon–aryl and germanium–aryl direct bonds on the semiconductor surface is a key issue to realize molecular electronic devices, but the conventional methods based on radical intermediates have problems to accompany the side reactions. We developed the first example of versatile and efficient methods to form clean organic monolayers with Si–aryl and Ge–aryl bonds on hydrogen-terminated silicon and germanium surfaces by applying our original catalytic arylation reactions of hydrosilanes and hydrogermanes using Pd catalyst and base in homogeneous systems. We could immobilize aromatic groups with redox-active and photoluminescent properties, and further applied in the field of rigid π-conjugated redox molecular wire composites, as confirmed by the successive coordination of terpyridine molecules with transition metal ions. The surfaces were characterized using cyclic voltammetry (CV), water contact angle measurements, X-ray photoelectron spectroscopy (XPS), fluorescence spectroscopy, and atomic force microscopy (AFM). Especially, the AFM analysis of 17 nm-long metal complex molecular wires confirmed their vertical connection to the plane surface.

Synthesis of optically active tertiary silanes via Pd-catalyzed enantioselective arylation of secondary silanes

Co-reporter:Yu Kurihara, Michihiro Nishikawa, Yoshinori Yamanoi and Hiroshi Nishihara

Chemical Communications 2012 vol. 48(Issue 94) pp:11564-11566

Publication Date(Web):24 Oct 2012

DOI:10.1039/C2CC36238D

We herein describe the development of an efficient enantioselective catalytic system that promotes the arylation of secondary silanes. Our method involves treatment of secondary silanes and aryl iodides with a Pd2(dba)3–asymmetric phosphoramidite ligand system to afford optically active tertiary silanes with good enantioselectivities.

Enhanced photocurrent production by photosystem I with modified viologen derivatives

Co-reporter:Yoshinori Yamanoi, Nao Terasaki, Mariko Miyachi, Yasunori Inoue, Hiroshi Nishihara

Thin Solid Films 2012 Volume 520(Issue 16) pp:5123-5127

Publication Date(Web):1 June 2012

DOI:10.1016/j.tsf.2012.03.133

This paper describes the construction of a photogenerated electron transfer system based on photosystem I (PSI) and modified molecular wires. Gold electrode surfaces were functionalized with sodium 3-mercapto-1-propanesulfonate and the 2,2′-dimethyl-4,4′-bipyridine cation to form a self-assembled monolayer, which enabled the subsequent immobilization of PSI. A higher photocurrent was observed in the presence of sodium ascorbate as an electron donor under irradiation at 680 nm.Highlights► Molecular wire was prepared by stepwise alkylation of 2,2′-dimethyl-4,4′-bipridine. ► Oxidation potentials of the modified molecular wire shifted negatively. ► Modified gold electrode showed a higher current density than that of previous system.

Preferential carbene insertion into Ge–H vs. other heavier group 14 hydridesviasamarium carbenoids

Co-reporter:Hitoshi Kondo, Yoshinori Yamanoi and Hiroshi Nishihara

Chemical Communications 2011 vol. 47(Issue 23) pp:6671-6673

Publication Date(Web):10 May 2011

DOI:10.1039/C1CC11256B

The relative reactivities of Zn, Al, and Sm carbenoids in the chemoselective carbene insertion reaction of heavier group 14 hydrides were studied. By variation of the reaction protocols using Sm carbenoids, insertion reaction can favour the Ge–H bonds to give Ge-alkylated derivatives in good to high yield.

Synthesis of vanadium-doped palladium nanoparticles for hydrogen storage materials

Co-reporter:Yuki Yamamoto;Mariko Miyachi

Journal of Nanoparticle Research 2011 Volume 13( Issue 12) pp:6333-6338

Publication Date(Web):2011 December

DOI:10.1007/s11051-011-0628-0

Palladium–vanadium (Pd/V) alloy nanoparticles stabilized with n-pentyl isocyanide were prepared as new hydrogen storage materials by a facile polyol-based synthetic route with tetraethylene glycol and NaOH at 250 °C. The size distribution of the nanoparticles thus obtained featured two peaks at 4.0 ± 1.1 and 1.4 ± 0.3 nm in diameter, which were the mixture of Pd/V alloy and Pd nanoparticles. The ratio between the number of Pd/V and that of Pd nanoparticles was 51:49, and the Pd:V ratio of the overall product was 9:1 in wt%, indicating that the 4.0 nm Pd/V nanoparticles were composed of 81% Pd and 19% V. The inclusion of vanadium caused the increase in the d-spacing and thus expansion of lattice constant. A rapid increase in hydrogen content at low H2 pressures was observed for the Pd/V nanoparticles, and a 0.47 wt% H2 adsorption capacity was achieved under a H2 pressure of 10 MPa at 303 K. Hydrogen storage performances of Pd/V alloy nanoparticles was superior compared with Pd nanoparticles.

Integrated Palladium-Catalyzed Arylation of Heavier Group14 Hydrides

Co-reporter:Dr. Aldes Lesbani ;Hitoshi Kondo;Yusuke Yabusaki;Dr. Misaki Nakai;Dr. Yoshinori Yamanoi;Dr. Hiroshi Nishihara

Chemistry - A European Journal 2010 Volume 16( Issue 45) pp:13519-13527

Publication Date(Web):

DOI:10.1002/chem.201001437

Abstract

A convenient procedure has been developed for the preparation of Group 14 compounds by integrated palladium-catalyzed cross-coupling of aromatic iodides with the corresponding Group 14 hydrides in the presence of a base. The reaction conditions can be applied to the cross-coupling of tertiary, secondary, and primary Group 14 compounds. In most cases, the desired arylated products were obtained in synthetically useful yields. Even in the case of aryl iodides containing OH, NH₂, CN, or CO₂R groups, the reactions proceeded with good to high yields with tolerance of these reactive functional groups. A possible application of this method is the unique synthesis of a fungicidal diarylmethyl(1H-1,2,4-triazol-1-ylmethyl)silane derivative.

Versatile Synthesis of Blue Luminescent Siloles and Germoles and Hydrogen-Bond-Assisted Color Alteration

Co-reporter:Yusuke Yabusaki;Norikazu Ohshima;Hitoshi Kondo;Tetsuro Kusamoto, Dr. ;Hiroshi Nishihara Dr.

Chemistry - A European Journal 2010 Volume 16( Issue 19) pp:5581-5585

Publication Date(Web):

DOI:10.1002/chem.200903408

Bio-inspired photoresponse of porphyrin-attached gold nanoparticles on a field-effect transistor

Co-reporter:Mariko Miyachi, Yoshinori Yamanoi, Kazuo Nakazato, Hiroshi Nishihara

Biochimica et Biophysica Acta (BBA) - Bioenergetics (September 2014) Volume 1837(Issue 9) pp:1567-1571

Publication Date(Web):September 2014

DOI:10.1016/j.bbabio.2013.11.012

Direct synthesis of alkylsilanes by platinum-catalyzed coupling of hydrosilanes and iodoalkanes

Co-reporter:Hikaru Inubushi, Hitoshi Kondo, Aldes Lesbani, Mariko Miyachi, Yoshinori Yamanoi and Hiroshi Nishihara