Laboratory of Polymeric and Composite Materials, Center of Innovation and Research in Materials and Polymers (CIRMAP), University of Mons UMONS, Place du Parc 20, 7000 Mons, Belgium.
J Org Chem. 2010 Mar 5;75(5):1561-8. doi: 10.1021/jo902490m.
The self-assembly of functional polythiophenes was studied by a bottom-up approach "from molecule to polymer". The synthesis and the X-ray structure of 2,5-dibromo-3-styryl and 3-2',3',4',5',6'-pentafluorostyryl-thiophenes revealed a supramolecular arrangement controlled by pi-pi interactions between the aromatic rings. A [2 + 2] photocyclization reaction in the solid state of (E)-1-2',5'-dibromo-3'-thienyl-2-pentafluorophenylethene triggers the formation of a rare cycloadduct comprising thiophene rings. The X-ray analysis confirmed its rctt stereochemistry. The synthesis of P3HT-b-P3ST and P3HT-b-P3STF block oligomers was achieved by a GRIM method in good yields. An indirect proof of well-defined nanostructured organization was provided by the partial photocyclization of pendant styryl moieties under UV irradiation.
通过“从分子到聚合物”的自下而上的方法研究了功能化聚噻吩的自组装。2,5-二溴-3-苯乙烯基和 3-2',3',4',5',6'-五氟苯乙烯基噻吩的合成和 X 射线结构揭示了由芳环之间的π-π相互作用控制的超分子排列。（E）-1-2',5'-二溴-3'-噻吩基-2-五氟苯乙烯的固态[2+2]光环化反应触发了罕见的噻吩环包含的环加成产物的形成。X 射线分析证实了其 rctt 立体化学。通过 GRIM 方法以良好的产率实现了 P3HT-b-P3ST 和 P3HT-b-P3STF 嵌段低聚物的合成。通过在紫外光照射下对侧链苯乙烯基部分进行部分光环化，提供了对定义良好的纳米结构组织的间接证明。
