122372-62-7Relevant academic research and scientific papers
Synthesis of large ring 3,4-alkylenedioxythiophenes (ADOT) derivatives via Mitsunobu reaction
Xu, Zhaochao,Kang, Joo-Hee,Wang, Fang,Paek, Seung-Min,Hwang, Seong-Ju,Kim, Youngmee,Kim, Sung-Jin,Choy, Jin-Ho,Yoon, Juyoung
supporting information; experimental part, p. 2823 - 2825 (2011/06/21)
Poly(3,4-ethylenedioxythiophene) (PEDOT) stands out for its optimized conductivity, stability, and high degree of transparency which has led to its successful commercialization. These excellent properties of PEDOT are mostly ascribed to the alkylenedioxy bridge across the 3- and 4-positions, and thus much effort has been dedicated to synthesizing 3,4-ethylenedioxythiophene (EDOT) analogs. However, only few homologous compounds were successfully synthesized, such as 3,4-propylenedioxythiophene (PrDOT) or 3,4-(1,4-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 way to modify ethylenedioxythiophenes (EDOTs), and these obtained ADOTs compounds are promising building blocks for the synthesis of functional π-conjugated systems used in material chemistry.
Synthesis and Reductive Desulfurization of Crown Ethers Containing Thiophene Subunit
Sone, Tyo,Sato, Kazuaki,Ohba, Yoshihiro
, p. 838 - 844 (2007/10/02)
Crown ethers containing 3,4-thiophenediyl and 3,4-thiophenediylbis(methylene) subunits as a ring constituent were prepared starting from 2,5-bis(ethoxycarbonyl)-3,4-thiophenediol and 2,5-dichloro-3,4-bis(chloromethyl)thiophene, respectively.A Raney nickel desulfurization of the thiophene-containing crown ethers afforded crown ethers having two adjacent side chains, such as a methyl or ethoxycarbonylmethyl group.The extraction ability of these crown ethers towards alkali metal cations was also examined by the solvent extraction method.
