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.
Bibliographical noteFunding Information:
We gratefully acknowledge the financial support from National Research Foundation of Korea (NRF) (SRC: 2011-0001340 , 2011-0001334 , NRL: 2010-0018895 ), WCU program (R31-2008-000-10010-0) and State Key Laboratory of Fine Chemicals of China (KF0809). We also thank Professor Bongjin Moon for his helpful discussion. Mass spectral data were obtained from the Korea Basic Science Institute (Daegu) on a Jeol JMS 700 high resolution mass spectrometer.
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Organic Chemistry