Synthesis of large ring 3,4-alkylenedioxythiophenes (ADOT) derivatives via Mitsunobu reaction
作者:Zhaochao Xu、Joo-Hee Kang、Fang Wang、Seung-Min Paek、Seong-Ju Hwang、Youngmee Kim、Sung-Jin Kim、Jin-Ho Choy、Juyoung Yoon
DOI:10.1016/j.tetlet.2011.03.062
日期:2011.6
4-butylenedioxy)thiophene (BuDOT). In this Letter, we use Mitsunobu reaction to synthesize a series of 3,4-alkylenedioxythiophenes (ADOTs) derivatives with 8- to 16-membered rings. The eight-membered compounds were obtained in high or excellent yield. We also found that the 9- to 16-membered EDOT analogs were obtained in relatively low yield because of the competitive reaction to make dimers. Our method provides an easy
聚(3,4-乙撑二氧噻吩)(PEDOT)以其优化的电导率,稳定性和高度透明性而著称,这使其成功实现了商业化。PEDOT的这些优异性能主要归因于3位和4位的亚烷基二氧基桥,因此,人们在合成3,4-乙撑二氧噻吩(EDOT)类似物上付出了很多努力。但是,只有很少的同源化合物能够成功合成,例如3,4-丙烯二氧噻吩(PrDOT)或3,4-(1,4-丁烯二氧基)噻吩(BuDOT)。在这封信中,我们使用Mitsunobu反应合成了一系列具有8至16元环的3,4-亚烷基二氧噻吩(ADOT)衍生物。以高收率或优异的收率获得了八元化合物。我们还发现,由于竞争性反应可生成二聚体,因此以相对较低的产率获得了9至16元的EDOT类似物。我们的方法提供了一种简单的方法来修饰乙二氧基噻吩(EDOT),并且这些获得的ADOTs化合物有望成为合成材料化学中使用的功能性π-共轭体系的基础。