4861-61-4

Basic information

• Product Name: 2-dodecylthiophene
• Synonyms: Thiophene, 2-dodecyl-
• CAS NO: 4861-61-4
• Molecular Formula: C₁₆H₂₈S
• Molecular Weight: 252.46
• Mol File: 4861-61-4.mol
• Article Data: 23

Chemical Properties

• Melting Point: -0.15°C (estimate)
• Boiling Point: 155°C/2mmHg(lit.)
• Appearance: /
• Density: 0.9125 (estimate)
• Refractive Index: 1.4850 to 1.4890
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: 2-dodecylthiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-dodecylthiophene(4861-61-4)
• EPA Substance Registry System: 2-dodecylthiophene(4861-61-4)

Safety Data

• Hazardous Substances Data: 4861-61-4(Hazardous Substances Data)

Usage

Description

2-Dodecylthiophene is a chemical compound with the molecular formula C16H26S, belonging to the thiophene family and featuring a dodecyl (12-carbon) alkyl chain. 2-dodecylthiophene is recognized for its solubility in organic solvents due to its long alkyl chain, which also allows for the design and modification of conjugated polymers with adjustable electronic and optical properties. The unique structure and characteristics of 2-dodecylthiophene render it an essential component in the development of sophisticated electronic materials.

Uses

Used in Electronics Industry:
2-Dodecylthiophene is utilized as a building block in the synthesis of organic materials for electronic applications. Its role in creating materials for organic light-emitting diodes (OLEDs) and organic photovoltaic cells is particularly noteworthy, where it contributes to the advancement of these technologies by enhancing their performance and efficiency.
Used in Material Science:
In the field of material science, 2-dodecylthiophene is employed as a component for designing conjugated polymers with tunable electronic and optical properties. This adaptability makes it a valuable asset for researchers and engineers looking to create materials with specific characteristics tailored to various applications.

Upstream product

• 10157-76-3 dodecyl 4-methylbenzenesulphonate 
• 355408-55-8 5,5-dimethyl-2-(thiophen-2-yl)-1,3,2-dioxaborinane 
• 112-53-8 1-dodecyl alcohol 
• 26447-67-6 1-(thiophen-2-yl)hexan-1-one 
• 111-46-6 diethylene glycol 
• 6790-19-8 1-thiopene-2-yl-dodecan-1-one 
• 143-15-7 1-dodecylbromide 
• 188290-36-0 thiophene 
• 4292-19-7 1-Iodododecane 
• 112-16-3 n-dodecanoyl chloride 

Downstream Products

• 1258753-94-4 C₆₂H₇₀O₈S₄ 
• 1258753-92-2 C₅₄H₆₆O₈S₂ 
• 1258753-84-2 C₆₀H₇₀O₈S₂ 
• 1250377-33-3 naphthalene-2,7-diyl bis(4-(5-dodecylthiophene-2-carbonyloxy)benzoate) 
• 153561-79-6 5,5'''-didodecyl-2,2':5',2'':5'',2'''-quaterthiophene 
• 1351206-31-9 C₄₀H₅₈O₄S₂ 
• 1351206-29-5 C₄₂H₆₂O₄S₂ 
• 1375353-61-9 C₃₀H₄₅O₆S^(1-)*Li⁽¹⁺⁾ 
• 1375353-56-2 sodium 2-(2-(2-(2-(4-(5-dodecylthiophen-2-yl)phenoxy)ethoxy)ethoxy)ethoxy)acetate 
• 1375353-50-6 2-(2-(2-(4-(5-dodecylthiophen-2-yl)phenoxy)ethoxy)ethoxy)ethanol 
• 1299470-13-5 C₂₂H₃₂OS 
• 1299469-87-6 2-dodecyl-5-(4-methoxyphenyl)thiophene 
• 506-30-9 Arachidic acid 
• 55373-89-2 methyl pentacosanoate 

Relevant articles and documents

Synthesis and photovoltaic properties of two-dimensional conjugated polythiophenes with bi(thienylenevinylene) side chains

Three two-dimensional (2-D) conjugated polythiophenes with bi(thienylenevinylene) side chains (biTV-PTs), P1, P2, and P3, were designed and synthesized for application in polymer solar cells. The absorption spectral, electrochemical, and photovoltaic properties of the biTV-PTs were investigated and compared with those of poly(3-hexylthiophene) (P3HT). The biTV-PTs show a broad absorption band from 350 to 650 nm; especially, the absorption spectrum of P3 displays a broad plateau and much stronger absorbance than that of P3HT in the wavelength range from 350 to 480 nm. Cyclic voltammograms reveal that the onset oxidation and reduction potentials of the biTV-PTs positively shifted by ca. 0.2 V in comparison with those of P3HT, indicating that the HOMO energy level of the biTV-PTs is ca. 0.2 eV lower than that of P3HT. Polymer solar cells (PSCs) were fabricated based on the blend of the polymers and 1-(3-methoxycarbonyl)propyl-1-phenyl-[6,6]-C-61 (PCBM) with a weight ratio of 1:1. The open circuit voltage of the PSCs based on the biTV-PTs is ca. 0.1 V higher than that of P3HT, which is benefited from the lower HOMO levels of the biTV-PTs. The maximum power conversion efficiency (PCE) of the PSCs based on P3 reached 3.18% under AM 1.5, 100 mW/cm2, which is 38% increased in comparison with that (2.41%) of the devices based on P3HT under the same experimental conditions. The results indicate that the 2-D conjugated biTV-PTs are promising polymer photovoltaic materials.

In search of efficient solubilizing groups for liquid and luminescent oligo(phenylene-thiophene) chromophores

In this work, the synthesis of oligomers having a rigid conjugated 4,4′-bis(2-thienyl)biphenyl fragment end-capped with various types of solubilizing groups (SGs), such as either alkyl or alkylsilyl or alkyl-oligodimethylsiloxane, has been reported. The comprehensive study of their thermal and optical properties as well as rheology in comparison to model highly crystalline oligomers with simple either hexyl or trimethylsilyl SGs allowed us to elucidate structure-property correlations and find the most powerful type of SG in terms of liquefaction for them. It was revealed that oligomers with long and branched alkyl SGs still retain high crystallinity, whereas oligomers with alkyl-oligodimethylsiloxane SGs combine very low glass transition temperatures (up to -111 °C) with a liquid-crystalline behaviour. The alkylsilyl SGs were found to be the most efficient, since the oligomers end-capped with trihexyl- and tri(2-butyloctyl)silyl SGs are liquid and have low values of both the glass transition temperature (up to -60 °C) and viscosity (up to 1.94 Pa s). All the oligomers prepared have similar optical absorption/luminescence spectra and high values of photoluminescence quantum yield in solution (90-95%) without a significant impact of the SG type. In the neat films, the type of SG has a huge impact on the shape and maxima of the absorption and luminescence spectra as well as the photoluminescence efficiency. Among this series of molecules, oligomers with alkylsilyl SGs demonstrate the highest values of photoluminescence quantum yield in the neat form (24-61%) and close to the solution optical characteristics, which indicates their strong capability to suppress aggregation of molecules in the bulk. Thus, for the first time liquid luminescent thiophene/phenylene co-oligomers were reported and the solubilizing capabilities of some of the most promising types of SG were comprehensively investigated and compared to each other. The results obtained can be used as a guideline for the design of functional materials based on conjugated oligomers with a tunable and controllable phase behaviour, solubility and optical properties in the neat state.

Thiadiazole quinoxaline-based copolymers with ～1.0 eV bandgap for ternary polymer solar cells

A new strong electron-deficient acceptor unit, 4,9-bis(5-bromothiophen-2-yl)-6,7-bis(5-dodecylthiophen-2-yl)-[1,2,5]thiadiazolo[3,4-g]quinoxaline (TQxT), is designed. Three TQxT based new conjugated polymers have been further developed by alternating with benzo[1,2-b:4,5-b′]dithiophene or naphtho[1,2-b:5,6-b′]difuran. Featuring ultra low bandgaps of 1.03-1.10 eV, these polymers exhibit absorption spectra beyond near-infrared (NIR) region. The polymer:PC71BM (1:2) solar cells deliver a best power conversion efficiency (PCE) of 0.43%. The doping of 9 wt% PBDTT-TQxP into P3HT:PC71BM (1:2) blend, however, leads to a highest PCE of 3.58% for the resultant ternary solar cells, corresponding to ～22% improvement in comparison to 2.93% PCE for P3HT:PC71BM binary cells.