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Quinoidal-Diketopyrrolopyrrole-Based Low-Bandgap n-Type Conjugated Polymers via Direct Arylation Polycondensation: Chalcogen Effects on Structures and Properties

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MACROMOLECULES 2024年第19期57卷 9006-9016页

作者： Rao, Mei Wang, Pai Shi, Yibo zhang, xuwen Han, Yang Deng, Yunfeng Geng, Yanhou Tianjin Univ Sch Mat Sci & Engn Tianjin Key Lab Mol Optoelect Sci Tianjin 300072 Peoples R China Tianjin Univ Key Lab Organ Integrated Circuits Minist Educ Tianjin 300072 Peoples R China Collaborat Innovat Ctr Chem Sci & Engn Tianjin Tianjin 300072 Peoples R China

Low-bandgap conjugated polymers (CPs) with strong absorption in the short-wave infrared region usually show ambipolar characteristics. Herein, three low-bandgap CPs, that is, PQF, PQT, and PQS, with unipolar n-type transport behavior were synthesized via direct arylation polycondensation (DArP) with quinoids based on terchalcogenophene-flanked diketopyrrolopyrrole (DPP) derivatives as C-Br monomers and less electron-rich (E)-1,2-bis (3,4-difluorothien-2-yl) ethene (4FTVT) as a C-H monomer, and the chalcogen effects on the isomerism of the quinoids and the properties of the resultant CPs were investigated. Thiophene-flanked DPP-containing quinoids are the mixtures of (E, E), (E, Z), and (Z, Z) isomers, while the sole (E, E) isomer is found in furan-flanked DPP-based quinoids and (Z, Z) isomer is dominant in the quinoids based on selenophene-flanked DPP. The quinoidal monomers are stable to undergo DArP. All three CPs show lower bandgaps of similar to 1.1 eV and unipolar n-type transport behavior with field-effect electron mobility (mu e) above 0.1 cm2 V-1 s(-1). Among them, the polymer PQF, comprising furan-flanked DPP, exhibits the highest mu e of 0.21 cm2 V-1 s(-1), possibly attributed to the simple chain conformation. This study provides a strategy to design low-bandgap unipolar n-type polymer semiconductors.

关键词： n-type conjugated polymers quinoidal structures low bandgap direct arylation polycondensation chalcogen effect

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Kinetics of naphthalene catalytic hydrogenation under high temperature and high pressure

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PETROLEUM SCIENCE AND TECHNOLOGY 2020年第3期38卷 266-270页

作者： Bie, Shiquan Jiang, Hongbo Wang, Wei Shu, Geping zhang, xuwen Wang, Hongxue Gao, Shansong East China Univ Sci & Technol Res Inst Petr Proc 130 Meilong Rd Shanghai Peoples R China East China Univ Sci & Technol Int Joint Res Ctr Green Energy Chem Engn Shanghai Peoples R China China Shenhua Coal Liquid & Chem Shanghai Res Ins Natl Engn Lab Direct Coal Liquefact Shanghai Peoples R China

The catalytic hydrogenation reaction of naphthalene was carried out on the Ni-Mo/Al2O3 catalyst by using a constant-temperature fixed-bed reactor with the temperature ranging from 315 degrees C to 400 degrees C and pressure ranging from 12 to 20 MPa. The model of naphthalene catalytic hydrogenation was proposed based on the Langmuir-Hinshelwood-Hougen-Watson competitive adsorption theory, and the model parameters were estimated. The results show that the hydrogenation reaction of naphthalene to tetralin is fast, and tetralin tends to form trans-decalin, while there is no direct conversion between trans-decalin and cis-decalin. The reaction activation energy of naphthalene to tetralin is the smallest.

关键词： Catalytic hydrogenation high temperature and high pressure kinetics naphthalene Ni-Mo Al2O3

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C-H/C-H Oxidative Direct Arylation Polycondensation to Isoindigo-Based n-Type Conjugated Polymers

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MACROMOLECULES 2024年第9期57卷 4158-4166页

作者： Shi, Yibo zhang, xuwen Wang, Tianzuo Rao, Mei Han, Yang Deng, Yunfeng Geng, Yanhou Tianjin Univ Sch Mat Sci & Engn Key Lab Organ Integrated Circuits Minist Educ Tianjin 300072 Peoples R China Tianjin Univ Tianjin Key Lab Mol Optoelect Sci Key Lab Organ Integrated Circuits Minist Educ Tianjin 300072 Peoples R China Collaborat Innovat Ctr Chem Sci & Engn Tianjin Tianjin 300072 Peoples R China Tianjin Univ Joint Sch Natl Univ Singapore & Tianjin Univ Int Campus Fuzhou 350207 Peoples R China

Two high molecular weight conjugated polymers (CPs), i.e., poly[N,N '-bis(4-tetradecyloctadecyl)-7,7 '-difluoroisoindigo-alt-2,2 '-bithiazole] (P2FI2Tz) and poly[N,N '-bis(4-tetradecyloctadecyl)-5,5 ',7,7 '-tetrafluoroisoindigo-alt-2,2 '-bithiazole] (P4FI2Tz), were synthesized via C-H/C-H oxidative direct arylation polycondensation (Oxi-DArP) using PdCl2/CuCl/Cu(OAc)(2) as catalytic system and chlorobenzene as solvent. Both polymers are unipolar n-type semiconductors with electron mobility (mu(e)) > 0.2 cm(2) V-1 s(-1), attributed to their low-lying highest occupied molecular orbitals (HOMOs) and lowest unoccupied molecular orbital (LUMOs), which are -6.01/-3.69 and -6.24/-3.82 eV for P2FI2Tz and P4FI2Tz, respectively. P2FI2Tz was also synthesized via C-Br/C-H direct arylation polycondensation (DArP) and Stille polycondensation. The resultant polymers P2FI2Tz-D and P2FI2Tz-S showed slightly lower mu(e) compared to Oxi-DArP-made polymer (P2FI2Tz-O1) with a similar molecular weight. Notably, Oxi-DArP is much faster and more efficient than DArP and Stille polycondensation. P2FI2Tz with a number-average molecular weight (M-n) above 40 kDa, was obtained in 9 h of Oxi-DArP, significantly shorter than 24 h with DArP and Stille polycondensation. P2FI2Tz with a M-n as high as 191 kDa could be synthesized via Oxi-DArP by extending the polymerization time to 16 h. Our results prove Oxi-DArP to be an efficient protocol to synthesize polymer semiconductors. This is also the first comparative study on three methods, i.e., Oxi-DArP, DArP, and Stille polycondensation.

关键词： Condensation Diffraction Monomers Organic reactions Polymers

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A BOUNDARY MAXIMUM PRINCIPLE FOR STATIONARY PAIRS OF VARIFOLDS WITH FIXED CONTACT ANGLE

arXiv

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arXiv 2022年

作者： zhang, xuwen School of Mathematical Sciences Xiamen University Xiamen361005 China Institut für Mathematik Goethe-Universität Frankfurt60325 Germany

In this note, we establish a boundary maximum principle for a class of stationary pairs of varifolds satisfying a fixed contact angle condition in any compact Riemannian manifold with smooth *** Codes 53C42, 49Q15 Cop... 详细信息

关键词： Maximum principle

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Direct Arylation Polycondensation toward Water/Alcohol-Soluble Conjugated Polymers: Influence of Side Chain Functional Groups

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ACS MACRO LETTERS 2021年第4期10卷 419-425页

作者： Zhao, Bowen Liang, Ziqi zhang, Ying Sui, Ying Shi, Yibo zhang, xuwen Li, Miaomiao Deng, Yunfeng Geng, Yanhou Tianjin Univ Sch Mat Sci & Engn Tianjin 300072 Peoples R China Tianjin Univ Tianjin Key Lab Mol Optoelect Sci Tianjin 300072 Peoples R China Tianjin Univ Joint Sch Natl Univ Singapore & Tianjin Univ Int Campus Fuzhou 350207 Peoples R China

Direct arylation of 2,7-dibromofluorene with n-octyl, 6-diethoxylphosphorylhexyl, 6-(N,N-diethylamino)hexyl or 6-bromohexyl side chains and 1,2,4,5-tetrafluorobenzene (TFB) were conducted to investigate the effect of side chain functional groups on the coupling, and the resulting TFB-substituted fluorene derivatives were used as C-H monomers for the synthesis of water/alcohol soluble conjugated polymers (WSCPs) by direct arylation polycondensation (DArP). The direct arylation and DArP of the monomers carrying phosphonate and amino groups went on smoothly in typical DArP conditions, that is, Pd(OAc)(2)/(PBu2Me)-Bu-t-HBF4/base/DMAc and Pd-2(dba)(3)center dot CHCl3/P(o-MeOPh)(3)/pivalic acid/base/THF, and high molecular weight polymers with these groups were successfully synthesized. However, for fluorenemonomers with bromohexyl side chains, the target products could not be obtained from the above conditions but could be prepared in the absence of carboxylic acid additives in low polar solvents. With the above DArP-made polymers as cathode interfacial layers, high performance organic solar cells (OSCs) were successfully fabricated.

关键词： Monomers Organic reactions Organophosphorus compounds Condensation Polymers

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Effect of hydrogenation of liquefied heavy oil on direct coal liquefaction

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FUEL 2017年 194卷 291-296页

作者： Shan Xiangen Shu Geping Li Kejian zhang xuwen Wang Hongxue Cao Xueping Jiang Hongbo Weng Huixin East China Univ Sci & Technol Res Inst Petr Proc Shanghai 200237 Peoples R China Natl Engn Lab Direct Coal Liquefact Shanghai 201108 Peoples R China

The effect of hydrotreatment of liquefied heavy oil on direct coal liquefaction (DCL) was studied by hydrogenating the liquefied heavy oil (initial boiling point greater than 320 degrees C) in a 30 ml continuous hydrogenation apparatus at operating conditions of pressure (P) 13-19 MPa, temperature (T) 360-400 degrees C, liquid space velocity (LHSV) 0.6-1.4 h(-1). After hydrogenation, the properties and hydrocarbon composition of liquefied heavy oil were regulated, leading to the enhancement of hydrogen donating ability and 5.6% increase in oil yield of DCL as compared with non-hydrogenated raw oil. Based on the results, a new method of preparing recycle solvent for direct coal liquefaction by mixing hydrogenated heavy oil and un-hydrogenated middle oil in a suitable proportion was proposed, which has been verified to be effective and efficient to increase oil yield. (C) 2017 Elsevier Ltd. All rights reserved.

关键词： Direct coal liquefaction Hydrogenation Liquefied product Hydrogenated oil Hydrogen-donating ability

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Employing supercritical n-butanol to remove the EVA film for the delamination of photovoltaic laminated module

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JOURNAL OF SUPERCRITICAL FLUIDS 2025年 219卷

作者： Wang, xuwen Liu, Zhifeng Ruan, Haoda Li, Xinyu zhang, Lei Hefei Univ Technol Sch Mech Engn Hefei 230009 Peoples R China Anhui Prov Key Lab Low Carbon Recycling Technol & Hefei 230009 Peoples R China State Key Lab Environm Adaptabil lndustrial Prod Guangzhou 510300 Peoples R China

The rapid advancement of the photovoltaic (PV) industry has elevated the recycling and reuse of decommissioned PV modules to critical challenges, essential for tackling environmental concerns and achieving resource reutilization. To facilitate the efficient layering of PV modules and recovery of valuable materials, this study proposes a PV module degradation and recycling process utilizing supercritical n-butanol. A systematic evaluation was conducted to assess the effects of various factors on the dissolution ratio of PV modules, with an appropriate range of process parameters selected for optimization. A second-order regression model was developed to predict the dissolution ratio of the EVA film. Comparison of actual dissolution ratio with model predictions confirmed the high accuracy of the fitted model. Finally, characterization and elemental analysis of cells recovered from the supercritical process demonstrated the effectiveness of this recycling method, achieving more thorough degradation on the cell surfaces.

关键词： Photovoltaic Supercritical n-butanol Degradation Recycling Characterization

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Diketopyrrolopyrrole-based conjugated polymers synthesized by direct arylation polycondensation for anisole-processed high mobility organic thin-film transistors

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JOURNAL OF MATERIALS CHEMISTRY C 2022年第7期10卷 2616-2622页

作者： Sui, Ying Wang, Zhongli Bai, Junhua Shi, Yibo zhang, xuwen Deng, Yunfeng Han, Yang Geng, Yanhou Tianjin Univ Sch Mat Sci & Engn Tianjin 300072 Peoples R China Tianjin Univ Tianjin Key Lab Mol Optoelectmn Sci Tianjin 300072 Peoples R China Tianjin Chengjian Univ Sch Mat Sci & Engn Tianjin 300384 Peoples R China Tianjin Univ Joint Sch Natl Univ Singapore & Tianjin Univ Int Campus Fuzhou 350207 Peoples R China

Two conjugated polymers (CPs) Fu-F and Fu-Cl that are soluble in a green solvent anisole were successfully synthesized via direct arylation polycondensation (DArP) using a furan-flanked diketopyrrolopyrrole (DPP) derivative (FDPP-Br) as the C-Br monomer and (E)-1,2-bis(3,4-difluorothien-2-yl)ethene (4FTVT) or (E)-1,2-bis(3,4-dichlorothien-2-yl)ethene (4ClTVT) as the C-H monomer. With anisole as the processing solvent and polyethylenimine ethoxylated (PEIE) as the electrode modification layer, n-type organic thin-film transistors (OTFTs) of the polymers were fabricated via bar-coating. The electron mobility (mu(e)) of the devices based on Fu-Cl was only in the magnitude of 10(-2) cm(2) V-1 s(-1), owing to the unfavoured fine granular film morphology. In contrast, Fu-F films showed fibre-like morphology with the polymer chains aligned along the bar-coating direction, which is favourable for the charge transport in OTFTs. Therefore, Fu-F delivered much better device performance with the mu(e) of up to 2.79 cm(2) V-1 s(-1). Our study demonstrates that green solvent processed high mobility CPs can be synthesized by DArP, an emerging eco-friendly protocol for the synthesis of CPs.

关键词： Conjugated polymers

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Explicit Solutions to the n-dimensional Semi-stationary Compressible Stokes Problem

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INTERNATIONAL JOURNAL OF THEORETICAL PHYSICS 2025年第2期64卷 1-11页

作者： zhang, Lijun Zhao, Qiong Huo, xuwen Khalique, Chaudry Masood Zhejiang Univ Sci & Technol Hangzhou 310023 Zhejiang Peoples R China Shandong Univ Sci & Technol Coll Math & Syst Sci Qingdao 266590 Shandong Peoples R China Zhejiang Scitech Univ Hangzhou Sch Comp Sci & Technol Zhejiang 3100018 Peoples R China North West Univ Fac Nat & Agr Sci Mat Sci Innovat & Modelling Res Focus Area Mafikeng Campus ZA-2735 Mmabatho South Africa

The n-dimensional semi-stationary compressible Stokes equations, established to model the dynamics of vortices in the Ginzburg-Landau theories in superconductivity, is a simplification of the isentropic compressible Navier-Stokes equations. This model equation can also be derived from the equations for the flows in compressible porous media in petroleum engineering or in compressible tissues. In this work, we investigate the n-dimensional semi-stationary compressible Stokes equations and obtain a family of explicit solutions in which the density does not change with space variables but decays to zero with time increasing exponentially, while the velocity is a quadratic polynomial of the space variables. It is worth pointing out that our results not only include the known results for n=2\documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \usepackage{upgreek} \setlength{\oddsidemargin}{-69pt} \begin{document}$$n=2$$\end{document} and n=3\documentclass[12pt]{minimal} \usepackage{amsmath} \usepackage{wasysym} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{amsbsy} \usepackage{mathrsfs} \usepackage{upgreek} \setlength{\oddsidemargin}{-69pt} \begin{document}$$n=3$$\end{document} in Xue and Dong (Int. J. Theor. Phys. 63(6), 151 (2024)), but also present the explicit solutions to the semi-stationary compressible Stokes equations in arbitrary higher dimensional space.

关键词： Compressible fluids Semi-stationary compressible Stokes problem Explicit solutions

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Organocatalytic Enantioselective Friedel- Crafts Reaction of 1-Naphthols with Isatins and an Unexpected Spontaneous Dehydration Process

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ASIAN JOURNAL OF ORGANIC CHEMISTRY 2014年第4期3卷 480-486页

作者： Wu, Deyan zhang, xuwen Xu, Yong Xue, Yingfei Li, Jian Wang, Wei Zhu, Jin E China Univ Sci & Technol Shanghai Key Lab New Drug Design Sch Pharm Shanghai 200237 Peoples R China Humanwell Healthcare Grp Co Ltd Wuhan 430075 Hubei Peoples R China Univ New Mexico Dept Chem & Chem Biol Albuquerque NM 87131 USA

An organocatalytic enantioselective Friedel-Crafts alkylation of 1-naphthols with isatins has been developed. The process is catalyzed by a simple cinchona alkaloid derived thiourea and gives biologically interesting, enantioenriched 3-(naphthalen-2-yl)-3-hydroxy-2-oxindoles in moderate to good yields of 42-83% and with good to high enantioselectivity of up to 94% ee. Furthermore, an unexpected intramolecular dehydration reaction proceeds spontaneously with 4-substituted 1-naphthols to offer structurally different ketone oxindoles.

关键词： Friedel-Crafts alkylation isatins naphthols organocatalysis oxindoles

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