由二茂铁亚胺环钯催化的Suzuki偶联反应合成具有发光性能的3-芳基噻吩

Synthesis of 3-Arylthiophenes with Luminescent Property via Suzuki Cross-coupling Reaction Catalyzed by Cyclopalladated Ferrocenylimine

3-芳基取代噻吩大多是电致发光材料的前体化合物.催化剂摩尔分数为0.5%的二茂铁亚胺环钯化合物在DMF/K3PO4/80℃条件下,能够有效地催化3-噻吩硼酸同芳基碘和芳基溴的Suzuki反应,方便地合成系列3-芳基噻吩衍生物.此方法操作简便,不需要加入过量的3-噻吩硼酸,催化剂用量小.化合物3b,3c和3d的发射光谱和激发光谱表明,此类化合物具有潜在的发光应用性能.

Aryl-substituted thiophenes are important fine chemicals and can constitute ubiquitous fragments of the active semiconducting layer in organic field effect transistors（OFETs）. Among the variety of useful methods for the synthesis of these kinds of compounds, palladium-catalyzed Suzuki cross-coupling reaction received more researchers＇ attentions. Cyclopalladated ferrocenylimines catalyzed Suzuki cross-coupling reaction of aryl iodides, bromides with 3-thienylboronic acid was carried out in DMF at 80℃ in the presence of K3PO4 and without the protection of inert gas. This method has the advantage of low loadings both of catalyst and 3-thienylboronic acid, simple and easy handling procedure. By using this method the synthesis of 3-arylthiophenes could be readily achieved. The emission and excitation spectra of compounds 3b, 3c, 3d confirmed that 3-arylsubstituted thiophenes were a kind of potential organic LEDs materials.