An analogue of EDOT, its polymer as cathodic electrochromic material with lower oxidation potentials, and greater stability than polythiophene.
3,4-(2,2-Dimethylpropylenedioxy)thiophene (ProDOT-Me2), a 3,4-ethylenedioxythiophene (EDOT) analogue, has a dimethylpropylene side group instead of ethylene while comparing to the EDOT.
3,4-(2,2-Dimethylpropylenedioxy)thiophene was prepared via trans-etherification by refluxing 3,4-dimethoxythiophene with 2,2-dimethylpropane-1,3-diol in toluene by using p-Toluenesulfonic acid as the catalyst. With lower oxidation potentials, and greater stability than polythiophene, conventional cathodic electrochromic material poly(3,4-propylenedioxythiophene) (PProDOT) exhibits very promising electrochromic performance with more rapid switching. Electrochromic window (ECW) based on PPro-DOT-Me2 shows switching speed for colouring and bleaching were almost 0.7 s in a range of +1.5 V to -1.5 V.
Over 10,000 cycles, with 75.7% as the maximum optical modulation and about 5 s as its response time for both colouring and bleaching processes can be achieved for the device with PProDOT-Me2 as the working electrode, bare indium tin oxide as the counter, and AgNO3, LiBr/Br2 as the electrolyte. Three colour states of transparent, blue, and opaque were demonstrated by applying various voltages.
|Molecular Weight||184.26 g/mol|
|Classification / Family||Thiophenes, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics|
|Purity||>97% (1H NMR in CDCl3)|
|Melting Point||45.0 °C|
|Appearance||Pale green/off-white powder/crystals|
Literature and Reviews
- Deterioration mechanism of electrochromic poly(3,4-(2,2-dimethylpropylenedioxy)thiophene) thin films, S. Guan et al., J. Mater. Chem. C, 4, 4584-4591 (2016); DOI: 10.1039/C6TC00930A.
- Flexible electrochromic device based on poly (3,4-(2,2-dimethylpropylenedioxy)thiophene), C. Ma et al., Electrochim. Acta, 54 (2), 598-605 (2008); DOI: 10.1016/j.electacta.2008.07.049.
- A novel photoelectrochromic device based on poly(3,4-(2,2-dimethylpropylenedioxy)thiophene) thin film and dye-sensitized solar cell, S. Yang et al., Sol. Energy Mater. Sol. Cells, 97, 186-190 (2012); DOI: 0.1016/j.solmat.2011.09.038.
- Electrochromic kinetics of nanostructured poly(3,4-(2,2-dimethylpropylenedioxy)thiophene) film on plastic substrate, C. Ma et al., Org. Electron., 12 (6), 980-987 (2011); 10.1016/j.orgel.2011.03.018.
- Partly Covered PProDOT-Me2 on MoS2 Nanosheets Counter Electrode for High-Performance Self-Powered Electrochromic Device, M. Khalifa et al., Adv. Mater. Interfaces, 9 (1), 2100945 (2022); DOI:10.1002/admi.202100945.
- Fabrication of fast switching electrochromic window based on poly(3,4-(2,2-dimethylpropylenedioxy)thiophene) thin film, R. Lakshmanan et al., J. Mater. Sci.: Mater. Electron. 27, 6035–6042 (2016); DOI: 10.1007/s10854-016-4527-0.
- A Transparent to Opaque Electrochromic Device Using Reversible Ag Deposition on PProDOT-Me2 with Robust Stability, K. Sheng et al., Adv. Opt. Mater., 9 (11), 2002149 (2021); DOI: 10.1002/adom.202002149.
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