Facile Synthesis of Thienopyrroledione-Based π-Conjugated Polymers via Direct Arylation Polycondensation under Aerobic Conditions

IF 5.1 1区化学 Q1 POLYMER SCIENCE Macromolecules Pub Date : 2018-08-23 DOI:10.1021/acs.macromol.8b01289

Akito Ichige, Hitoshi Saito, Junpei Kuwabara, Takeshi Yasuda, Jun-Chul Choi, Takaki Kanbara*

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引用次数: 22

Abstract

An exploration of the tolerance of a Pd-catalyzed direct arylation polycondensation under aerobic conditions was carried out. The polycondensation of 5-(2-ethylhexyl)thieno-[3,4-c]-pyrrole-4,6-dione with 2,7-dibromo-9,9-dioctylfluorene was accomplished smoothly in air by refluxing the solvents, without the need for additional catalysts or additives. This simple modification allowed the use of commercially available reagent-grade solvents without further purification and produced the corresponding π-conjugated polymer with a molecular weight and yield comparable to those obtained under conventional oxygen- and moisture-free conditions. The facile synthetic protocol was applicable to the synthesis of other thienopyrroledione-based π-conjugated polymers. The obtained polymers served as semiconducting materials in organic light-emitting diodes (OLEDs) and organic photovoltaics. The effects of the terminal structure of the polymer on its photoluminescence and OLED device characteristics were also evaluated.

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好氧条件下直接芳基化缩聚制备噻吩吡咯二酮基π共轭聚合物

探索了在有氧条件下pd催化的直接芳基化缩聚的耐受性。5-(2-乙基己基)噻吩-[3,4-c]-吡咯-4,6-二酮与2,7-二溴-9,9-二辛基芴在空气中通过回流溶剂顺利缩聚，无需额外的催化剂或添加剂。这种简单的改性允许使用市售的试剂级溶剂，而无需进一步纯化，并产生相应的π共轭聚合物，其分子量和产率可与常规无氧和无湿条件下获得的聚合物相媲美。该简易合成方法同样适用于其他噻吩吡咯二酮基π共轭聚合物的合成。所得聚合物可作为有机发光二极管(oled)和有机光伏的半导体材料。研究了聚合物的末端结构对其光致发光和OLED器件特性的影响。

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来源期刊

Macromolecules 工程技术-高分子科学

CiteScore

9.30

自引率

16.40%

发文量

942

审稿时长

2 months

期刊介绍： Macromolecules publishes original, fundamental, and impactful research on all aspects of polymer science. Topics of interest include synthesis (e.g., controlled polymerizations, polymerization catalysis, post polymerization modification, new monomer structures and polymer architectures, and polymerization mechanisms/kinetics analysis); phase behavior, thermodynamics, dynamic, and ordering/disordering phenomena (e.g., self-assembly, gelation, crystallization, solution/melt/solid-state characteristics); structure and properties (e.g., mechanical and rheological properties, surface/interfacial characteristics, electronic and transport properties); new state of the art characterization (e.g., spectroscopy, scattering, microscopy, rheology), simulation (e.g., Monte Carlo, molecular dynamics, multi-scale/coarse-grained modeling), and theoretical methods. Renewable/sustainable polymers, polymer networks, responsive polymers, electro-, magneto- and opto-active macromolecules, inorganic polymers, charge-transporting polymers (ion-containing, semiconducting, and conducting), nanostructured polymers, and polymer composites are also of interest. Typical papers published in Macromolecules showcase important and innovative concepts, experimental methods/observations, and theoretical/computational approaches that demonstrate a fundamental advance in the understanding of polymers.