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Effect of Oxyethylene Chains on Characteristics of N-Type Semiconducting Polymers

Journal of Fiber Science and Technology 2025年第3期81卷 33-41页

作者： Kawakami, Momoko Fu, Hongyu Akai, Nobuyuki Ogino, Kenji Graduate School of Bio-Applications and Systems Engineering Tokyo University of Agriculture and Technology 2-24-16 Nakacho Koganei Tokyo184-8588 Japan

Polymeric materials have been extensively utilized as electron transport (n-type) materials in organic solar cells instead of conventional fullerene derivatives due to their superior optoelectronic properties and stability. Among them, polymers with a structure comprising fused heterocyclic multi-ring aromatic units, and branched alkyl side chains ensuring solubility have been focused on. However, from the perspective of electron transport, the branched alkyl chains might hinder the stacking of conjugated systems. We proposed the molecular design, where highly flexible oxyethylene groups as side chains are incorporated aiming to achieve an optimal balance between electron mobility and solubility. We synthesized the conjugated polymer, P(NDI2O4C6-T2) consisting of naphthalene dimide as the main chain, and linear hexyl tetra(oxyethylene) group as the side chain (3, 6, 9, 12-tetraoxaoctadecyl group), and evaluated the basic properties including electron mobility. For comparison, analogues with linear octyl and branched 2-octyldodecyl groups, P(NDI2C8-T2) and P(NDI2OD-T2) were also prepared. Consequently P(NDI2O4C6-T2) exhibited the highest electron mobility and solubility in conventional organic solvents. Quantum chemical calculations were also carried out to verify the experimental results based on the intra- and intermolecular interaction in the polymer. ©2025 The Society of Fiber Science and Technology, Japan.

关键词： Naphthalene

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Hydrochar Prepared from Aquatic and Terrestrial biomass: Comparative Analysis of Characteristics and applications

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bioResources 2025年第2期20卷 3838-3847页

作者： Gao, Libing Wang, Zifei Guo, Jinyu Qiao, Yifan Wang, Shuai Cui, Mengke Zhang, Xuan Guo, Yuhan Wang, Jianghao Zhang, Tong Ogino, Kenji Wang, Bing School of Environment and Resources Taiyuan University of Science and Technology 66 Wa-liu Road Shanxi Taiyuan030024 China School of Pharmacy Youjiang Medical University for Nationalities Guangxi Baise533000 China Graduate School of Bio-Applications and Systems Engineering Tokyo University of Agriculture and Technology Tokyo Koganei184-8588 Japan

The benefits of hydrothermal carbonization (HTC) for carbon sequestration, energy, and soil remediation are widely recognized. Up to the present, there has been much research on hydrochar from terrestrial biomass residues, but there is little research on hydrochar based on aquatic plants. In this study, the physical and chemical properties of water hyacinth (representative of aquatic plants) and corn stalk (representative of terrestrial plants) were systematically analyzed under the condition of single hydrothermal carbonization. The results showed that water hyacinth-based hydrochar (WHHC) had well-developed pores, rich functional groups, and high nitrogen content. Among them, the nitrogen content of WHHC was 3.83%, which was more than three times the nitrogen content of corn straw-based hydrothermal carbon (CSHC) (1.11%), and the number of micropores, mesoporous pores, and macropores were also higher than that of CSHC. These differences were attributed to the contrasting growing environments and main components of water hyacinth and corn stalk. These differences revealed their potential application directions: WHHC can be used as an adsorbent and soil amendment;CSHC is more suitable as a supplementary energy source because of its higher carbon content and stability. © 2025, North Carolina State University. All rights reserved.

关键词： biomass Hydrochar Physical and chemical properties Waste utilization

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Polymer chain dynamics .1. Estimation of orientational auto-correlation function for polymer chains

POLYMER JOURNAL

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POLYMER JOURNAL 1996年第7期28卷 576-581页

作者： Tsunomori, F Ushiki, H Graduate School of Bio-Applications and Systems Engineering Tokyo University of Agriculture and Technology

Fluorescence anisotropy decay curves of polystyrene labeled with an anthryl group in the middle of a main chain (PSAPS) were measured by the time-resolved fluorescence depolarization method. We studied an adequate orientational auto-correlation functions (OACF) to explain fluorescence anisotropy decay curves of PSAPS. The goodness of fitting to measured anisotropy decays is evaluated by an original fitting program based on Wahl's argolithm. However it was difficult to distinguish the most adequate OACF from many reported ones only by the comparison of the values of the residual sum or squares. Consideration of the meaning of variable parameters contained in many OACF reported has been done from the viewpoint that OACF should refrect the distribution of relaxation rate. Furthermore, a novel method for estimation of OACF called chi(2)-map method was used. As a result the hyperbolic function is one of the most adequate OACF in order to express effectively the fluorescence anisotropy decay curves of PSAPS chains.

关键词： fluorescence depolarization polystyrene X(2)-map long time tail hyperbolic function

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Polymer chain dynamics .3. Intermittent orientational relaxation of terminal segment on polystyrene chain

POLYMER JOURNAL

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POLYMER JOURNAL 1996年第7期28卷 588-593页

作者： Tsunomori, F Ushiki, H Graduate School of Bio-Applications and Systems Engineering Tokyo University of Agriculture and Technology

Polystyrene having an anthryl group attached at the end of a chain, whose degree of polymerization is 550, was used. We have found that the most appropriate orientational auto-correlation function for a terminal segment on a chain is hyperbolic function r(t)similar to r(0)(t/tau(eff))(-beta). This behavior indicates the primary process of of orientational relaxation of chain segments to be the intermittent process. The distribution of the state density of a terminal segment is in agreement with that of ''inner'' segment according to the reference temperature T-x, which reflects to the characteristic activation energy of orientational relaxation of segments. Therefore the characteristic activation energy of orientational relaxation of a segment is independent of position on a chain. The values of minimum reaction radii xi(0) of a terminal segment were about twice times larger than that of a central segment. This behavior can be reduced to the degree of freedom of segmental motion on the basis of computer simulation. Therefore xi(0) corresponds not only the apparent activation energy of solvent molecules but the degree of freedom of segmental motion on a polymer chain.

关键词： intermittent process hyperbolic function terminal group polystyrene fluorescence depolarization

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DEM simulation of polydisperse systems of particles in a fluidized bed

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Particuology 2009年第1期7卷 9-18页

作者： Nobuyuki Tagami Ajit Mujumdar Masayuki Horio Bio Applications and Systems Engineering Tokyo University of Agriculture & TechnologyNaka-choKoganei-shiTokyo 184-8588Japan

Numerical simulations based on three-dimensional discrete element model （DEM） are conducted for mono-disperse, binary and ternary systems of particles in a fluidized bed. Fluid drag force acting on each particle depending on its size and relative velocity is assigned. The drag coefficient corresponding to Ergun＇s correlation is applied to the system of fluidized bed with particle size ratios of 1：1 for the mono-disperse system, 1：1.2, 1：1.4 and 1：2 for the binary system and 1：1.33：2 for the ternary system by keeping total volume and surface area of the particles constant. Results indicated that a reasonable estimation of drag force based on individual particle diameters as compared to that of the mean diameter of the particles is achieved in the fluid cells. The total translational kinetic energy of the particles is found to increase as the particle size ratio increases, suggesting an enhanced momentum transfer in polydisperse particle systems. systems with wide particle size distribution exhibited higher particle velocities around bubbles, resulting in faster bubble growth and its subsequent rise through the fluidized bed.

关键词： Discrete element method Fluid drag force Fluidized bed Particle size distribution

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Recent progress of organic nonlinear optics in Japan

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SYNTHETIC METALS 1996年第2-3期81卷 99-115页

作者： Miyata, S Tao, XT Graduate School of Bio-Applications and Systems Engineering Tokyo University of Agriculture and Technology Koganei Tokyo 184 Japan

In the field of nonlinear optics (NLO), the organic materials are relative newcomers compared to inorganic single crystals and semiconductors. In this paper, we give a review on the recent progress of organic NLO in Japan. This includes: (1) molecular design strategies, (2) thin-film forming techniques, (3) phase-matching methods, (4) single crystals for blue second-harmonic generation, (5) electro-optic polymers. We show a number of achievements on organic NLO that have been obtained in Japan;further studies should be done to realize practical applications of organic NLO.

关键词： nonlinear optics Japan

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Preparation of monodisperse microspheres using the Shirasu porous glass emulsification technique

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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND engineering ASPECTS 1996年 109卷 97-107页

作者： Omi, S Graduate School of Bio-Applications and Systems Engineering Tokyo University of Agriculture and Technology Nakamachi Koganei Tokyo 184 Japan

Relatively uniform polymeric microspheres, with diameters ranging from 2.5 to 60 mu m, and relative standard deviations of diameters close to 10%, were prepared by the ordinary suspension polymerization of either styrene-(hydrophobic) or methyl methacrylate (MMA)-(more hydrophilic) based monomers. Unlike the conventional stirred-tank system, a particular microporous glass membrane (Shirasu porous glass;SPG) provided uniform monomer droplets continuously when monomer was allowed to permeate through the micropores under a carefully controlled nitrogen atmosphere. The monomer droplets, a mixture of monomers, diluents, oil-soluble initiator as well as water-insoluble reagent, were then suspended in the aqueous solution containing stabilizing agents, transferred to a stirred vessel and polymerized. In the case of hydrophilic MMA spheres, the size distribution tends to become broader because hydrophilic substances easily wet the surface of SPG, leading to a permeation process which is uncontrollable. This difficulty was overcome by adopting the droplet swelling technique, in which the secondary emulsion droplets containing hydrophilic MMA were absorbed in the primary emulsion droplets consisting of hydrophobic components on the principle of the degradative diffusion process. Uniformity of the initial droplets is preserved during the swelling step, and subsequent polymerization. applications of crosslinked microporous spheres were promising as packing beads for gel permeation chromatography and as carriers for enzyme immobilizations.

关键词： membrane emulsification monosized particles poly methylmethacrylate polystyrene Shirasu porous glass suspension polymerization

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A new method for solving the permutation problem of frequency-domain blind source separation

A new method for solving the permutation problem of frequenc...

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作者： Hu, Xuebin Kobatake, Hidefumi Graduate School of Bio-Applications and Systems Engineering Tokyo University of Agriculture and Technology Koganei-shi 184-8588 Japan Graduate School of Bio-Applications and Systems Engineering Tokyo University of Agriculture and Technology Japan Graduate School of Bio-Applications and Systems Engineering Japan

Frequency domain blind source separation has the great advantage that the complicated convolution in time domain becomes multiple efficient multiplications in frequency domain. However, the inherent ambiguity of permutation of ICA becomes an important problem that the separated signals at different frequencies may be permuted in order. Mapping the separated signal at each frequency to a target source remains to be a difficult problem. In this paper, we first discuss the inter-frequency correlation based method [1], and propose a new method using the continuity in power between adjacent frequency components of same source. The proposed method also implicitly utilizes the information of inter-frequency correlation, as such has better performance than the previous method. Copyright © 2005 The Institute of Electronics, Information and Communication Engineers.

关键词： Blind source separation

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Structure-activity relationships of cyclopropene compounds, inhibitors of pheromone biosynthesis in Bombyx mori

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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 1996年第10期44卷 3350-3354页

作者： Ando, T Ohno, R Ikemoto, K Yamamoto, M Graduate School of Bio-Applications and Systems Engineering Tokyo University of Agriculture and Technology Fuchu Tokyo 183 Japan

According to the synthetic route for 11,12-methylenehexadec-11-enoic acid [10-(2-butyl-1-cyclopropenyl)decanoic acid] and the amide, their related cyclopropene compounds, which possessed a propene ring at the 7,8-, 9,10-, or 13,14-position in a C-16 chain and the 11,12-position in a C-14 or C-18 chain, were synthesized via the corresponding 1-alkyl-1,2,2-tribromocyclopropane. Their activities as biosynthetic inhibitors of bombykol [(10E,12Z)-10,12-hexadecadien-1-ol;sex pheromone of the silkworm moth Bombyx mori L.] were measured with virgin female silkworm moths in vivo. The 7,8-methylene compounds were inactive even at the dose of 10 mu g/gland, but other compounds at 1 mu g/gland inhibited the conversion of [16,16, 16-H-2(3)]hexadecanoic acid to bombykol to some extent. Each amide showed stronger inhibitory activity than the corresponding acid, and the 11,12-methylene amide with a C-16 chain was the strongest (I-50 = 0.016 mu g/gland) among the tested compounds. Furthermore, experiments comparing the incorporation of [1-C-14]hexadecanoic acid into bombykol and another alcohol component in the pheromone gland, (Z)-11-hexadecen-1-ol, suggested that the all-desaturation was blocked by 9,10- and 11,12-methylene compounds and the subsequent Delta 10,- 12-desaturation by 11,12- and 13,14-methylene compounds.

关键词： cyclopropene desaturase pheromone biosynthesis cyclopropenes structure-activity relationships bombykol biosynthesis Delta 11-desaturation

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Synthesis and electric properties of one-dimensional polymers of metallophthalocyanine with octakis-substituents of acceptor groups

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SYNTHETIC METALS 1997年第1-3期84卷 353-354页

作者： Morimoto, K Kim, SJ Shigehara, K Graduate school of Bio-Applications & Systems Engineering Tokyo University of Agriculture & Technology 2-24-16 Nakacho Koganei Tokyo 184 Japan

One-dimensional metallophthalocyanine polymers adopt a favorable conformation for the enhancement of electric conductivity. Metallophthalocyanine derivatives with octakis-substituents of donor or acceptor groups, especially with octa-cyano substituents as acceptor groups are also known to increase the electric conductivity. In the present study, octacyanometallophthalocyanine (MPcOC, M=Si, Fe) monomeric and polymeric complexes were synthesized and their electric and electrochemical properties were investigated. Each complex showed reversible redox wave at near 0 volt, exhibiting the strong acceptor properties. The polymeric complexes gave electric conductivity of 10(-6) S/cm without any doping process.

关键词： octacyanophthalocyanine phthalocyanine polymer electric conductivity cyclic voltammetry

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