3,4-(2,2-Dimethylpropylenedioxy)thiophene

CAS Number 255901-50-9

Chemistry Building Blocks, Heterocyclic Building Blocks, Materials, Monomers

3,4-(2,2-Dimethylpropylenedioxy)thiophene

An analogue of EDOT, its polymer as cathodic electrochromic material with lower oxidation potentials, and greater stability than polythiophene.

Specifications | MSDS | Literature and Reviews

3,4-(2,2-Dimethylpropylenedioxy)thiophene (ProDOT-Me2, CAS number 255901-50-9), 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.

Thiophene derivative building block

for the synthesis of OLED and organic photovoltaic materials

Worldwide shipping

Quick and reliable shipping

Substituted with dimethylpropylene group

for lower oxidation potentials and greater stability

High purity

>97% Purity

General Information

CAS Number	255901-50-9
Chemical Formula	C₉H₁₂O₂S
Full Name	3,4-(2,2-Dimethylpropylenedioxy)thiophene
Molecular Weight	184.26 g/mol
Synonyms	3,4-Dihydro-3,3-dimethyl-2H-thieno[3,4-b-1,4]dioxepine, ProDOT-Me2
Classification / Family	Thiophenes, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics

Chemical Structure

Product Details

Purity	>97% (¹H NMR in CDCl₃)
Melting Point	45.0 °C
Appearance	Pale green/off-white powder/crystals

MSDS Documentation

3,4-(2,2-Dimethylpropylenedioxy)thiophene MSDS Sheet

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.