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Low-Cost Synthesis and Physical Characterization of Thieno[3,4-c]pyrrole-4,6-dione-Based Polymers
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2012-09-13 00:00:00 , DOI: 10.1021/jo301512e
Philippe Berrouard 1 , Stéphane Dufresne 1 , Agnieszka Pron 1 , Justine Veilleux 1 , Mario Leclerc 1
Affiliation  

The improved synthesis of thieno[3,4-c]pyrrole-4,6-dione (TPD) monomers, including Gewald thiophene ring formation, a Sandmeyer-type reaction, and neat condensation with an amine, is presented. This protocol enables faster, cheaper, and more efficient preparation of TPD units in comparison to traditional methods. Furthermore, a series of TPD homo- and pseudohomopolymers bearing various alkyl chains was synthesized via a direct heteroarylation polymerization (DHAP) procedure. UV–visible absorption and powder X-ray diffraction measurements revealed the relationship between the ratio of branched to linear alkyl chains and the optoelectronic properties of the polymers as well as their packing in the solid state.

中文翻译:

噻吩并[3,4- c ]吡咯-4,6-二酮基聚合物的低成本合成及物理表征

提出了改进的噻吩并[3,4- c ]吡咯-4,6-二酮(TPD)单体的合成方法,包括Gewald噻吩环形成,Sandmeyer型反应以及与胺的纯净缩合反应。与传统方法相比,该协议可以更快,更便宜,更有效地制备TPD装置。此外,通过直接杂芳基聚合(DHAP)程序合成了一系列带有各种烷基链的TPD均聚物和假均聚物。紫外可见吸收和粉末X射线衍射测量揭示了支链与直链烷基链之比与聚合物的光电特性及其在固态状态下的堆积之间的关系。
更新日期:2012-09-13
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