Synthesis of large ring 3,4-alkylenedioxythiophenes (ADOT) derivatives via Mitsunobu reaction

Zhaochao Xu, Joo Hee Kang, Fang Wang, Seung Min Paek, Seong Ju Hwang, Youngmee Kim, Sung Jin Kim, Jin Ho Choy, Juyoung Yoon

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Abstract

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.

Original languageEnglish
Pages (from-to)2823-2825
Number of pages3
JournalTetrahedron Letters
Volume52
Issue number22
DOIs
Publication statusPublished - 2011 Jun 1

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Xu, Z., Kang, J. H., Wang, F., Paek, S. M., Hwang, S. J., Kim, Y., Kim, S. J., Choy, J. H., & Yoon, J. (2011). Synthesis of large ring 3,4-alkylenedioxythiophenes (ADOT) derivatives via Mitsunobu reaction. Tetrahedron Letters, 52(22), 2823-2825. https://doi.org/10.1016/j.tetlet.2011.03.062