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

Title
Synthesis of large ring 3,4-alkylenedioxythiophenes (ADOT) derivatives via Mitsunobu reaction
Authors
Xu Z.Kang J.-H.Wang F.Paek S.-M.Hwang S.-J.Kim Y.Kim S.-J.Choy J.-H.Yoon J.
Ewha Authors
김성진김영미윤주영최진호황성주
SCOPUS Author ID
김성진scopus; 김영미scopus; 윤주영scopus; 최진호scopus; 황성주scopus
Issue Date
2011
Journal Title
Tetrahedron Letters
ISSN
0040-4039JCR Link
Citation
vol. 52, no. 22, pp. 2823 - 2825
Indexed
SCI; SCIE; SCOPUS WOS scopus
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. © 2011 Elsevier Ltd. All rights reserved.
DOI
10.1016/j.tetlet.2011.03.062
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자연과학대학 > 화학·나노과학전공 > Journal papers
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