155861-77-1

Basic information

• Product Name: 3 4-PROPYLENEDIOXYTHIOPHENE 97
• Synonyms: 3 4-PROPYLENEDIOXYTHIOPHENE 97;3,4-Dihydro-2H-thieno[3,4-b][1,4]dioxepin, ProDOT;3,4-DIHYDRO-2H-THIENO[3,4-B][1,4]DIOXEPINE
• CAS NO: 155861-77-1
• Molecular Formula: C₇H₈O₂S
• Molecular Weight: 156.204
• Mol File: 155861-77-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 79-83 °C
• Boiling Point: 229.704°C at 760 mmHg
• Flash Point: 92.722°C
• Appearance: /
• Density: 1.244g/cm³
• Vapor Pressure: 0.104mmHg at 25°C
• Refractive Index: 1.55
• CAS DataBase Reference: 3 4-PROPYLENEDIOXYTHIOPHENE 97(CAS DataBase Reference)
• NIST Chemistry Reference: 3 4-PROPYLENEDIOXYTHIOPHENE 97(155861-77-1)
• EPA Substance Registry System: 3 4-PROPYLENEDIOXYTHIOPHENE 97(155861-77-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 155861-77-1(Hazardous Substances Data)

Usage

Uses

PRODOT can be used as a conjugated polymer in the fabrication of dye sensitized solar cells (DSSCs), sensors and electrochromic materials.

General Description

3,4-Propylenedioxythiophene (PRODOT) is a conductive polymer that forms a π-conjugated system. It has good electrochromic properties with high conductivity and surface electroactivity. It forms a thin film by using layer by layer (LBL) technique and spin coating.

InChI:InChI=1/C7H8O2S/c1-2-8-6-4-10-5-7(6)9-3-1/h4-5H,1-3H2

Upstream product

• 177364-94-2 3,4-Dihydro-2H-thieno[3,4-b][1,4]dioxepine-6,8-dicarboxylic acid diethyl ester 
• 51792-34-8 2,3-dimethoxythiophene 
• 504-63-2 trimethyleneglycol 
• 177364-98-6 3,4-dihydro-2H-thieno[3,4-b][1,4]dioxepine-6,8-dicarboxylic acid 

Downstream Products

• 738625-77-9 2,5-bis(hydroxyphenylethyl)-3,4-(propane-1,3-diyldioxy)thiophene 

Relevant articles and documents

Facile polymerization method for poly(3,4-ethylenedioxythiophene) and related polymers using iodine vapour

A novel iodine vapour promoted polymerization method of 2,5-dibromo-3,4-ethylenedioxythiophene, and 2,5-diiodo-3,4-ethylenedioxythiophene and their derivatives at room temperature without using any solvent has been developed. The resulting polymers are co

Diprotodecarboxylation reactions of 3,4-dialkoxythiophene-2,5-dicarboxylic acids mediated by AG2CO3 and microwaves

An efficient and rapid method is reported to obtain 3,4-dialkoxythiophenes from 3,4-dialkoxythiophene-2,5-dicarboxylic acids through a diprotodecarboxylation reaction with Ag2CO3/AcOH as a catalytic system and microwave heating in dimethylsulfoxide (DMSO) as solvent. This methodology lets us obtain for the first time good performance with thiophenes bearing strong electron-donating groups such as alkoxides. This methodology eliminates the usage of harmful quinoline as solvent, as well as the long reaction times typically used (12-18 h) to obtain the 3,4-dialkoxythiophenes. The reaction of 7 diacids showed good yields (60-89%) following 20 min of microwave heating in a temperature range of 120-150 °C. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

Hydrogen bonding and steric effects on rotamerization in 3,4-alkylenedioxy-, 3-alkoxy- and 3,4-dialkoxy-2-thienyldi(tert-butyl)-methanols: An NMR, IR and X-ray crystallographic study

The equilibrium constant for the anti ? syn rotamerization (anti: intramolecularly hydrogen-bonded hydroxy group; syn: "free" hydroxy group) of 3,4-alkylenedioxy-, 3-alkoxy- and 3,4-dialkoxy-2-thienyldi(tert-butyl)methanols depends on the 3,4-alkylenedioxy or alkoxy group(s) and the solvent, hydrogen-bonding solvents such as DMSO and pyridine favouring the syn isomer. Equilibrium constants ([syn]/[anti]) in chloroform and benzene decrease in the order: 3,4-OCH2O-, 3,4-O(CH2)2O-, 3-OMe, 3-OEt, 3,4-(OMe)2 ≈ 3-Oi-Pr, 3,4-(OEt)2, ranging over about 2.5 orders of magnitude. Variations in the IR OH stretching frequencies and the NMR OH proton shifts for the anti isomer indicate that intramolecular hydrogen bonding increases in roughly the same order. The syn → anti rotation barrier in DMSO increases with substituent size and number. The 3,4-methylenedioxythienyl derivative has a rather lower barrier (17.5 kcal mol-1) than all the others (21.0-22.3 kcal mol-1). The syn → anti rotation barrier is largely determined by steric effects but intramolecular hydrogen bonding in the anti isomer contributes to the variation of the anti → syn rotation barrier. A single crystal X-ray diffraction study of the anti-3,4-diethoxy derivative shows that the orientation of the 3-alkoxy group is very different from that in anti-3-methoxy-2-thienyldi-(1-adamantyl)methanol. Molecular mechanics and quantum mechanical calculations are used in an attempt to rationalize the equilibrium data.