104934-52-3

Basic information

• Product Name: 3-DODECYLTHIOPHENE
• Synonyms: 3-N-LAURYLTHIOPHENE;3-N-DODECYLTHIOPHENE;3-DODECYLTHIOPHENE;3-DODECYLTHIOPHENE 97%;3-Laurylthiophene;二吩噻
• CAS NO: 104934-52-3
• Molecular Formula: C₁₆H₂₈S
• Molecular Weight: 252.46
• Product Categories: Thiophenes;pharmacetical;3-Alkylthiophenes (for Conduting Polymer Research);Functional Materials;Reagents for Conducting Polymer Research;Thiophen;Organic Electronics and Photonics;Synthetic Tools and Reagents;Thiophene Monomers and Building Blocks;Thiophene Series;OPV,OLED;Pyrazines ,Pyrans
• Mol File: 104934-52-3.mol
• Article Data: 26

Chemical Properties

• Melting Point: -0.15°C (estimate)
• Boiling Point: 290 °C(lit.)
• Flash Point: >230 °F
• Appearance: clear colorless to yellow liquid
• Density: 0.902 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000276mmHg at 25°C
• Refractive Index: n20/D 1.488(lit.)
• Storage Temp.: 0-6°C
• CAS DataBase Reference: 3-DODECYLTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-DODECYLTHIOPHENE(104934-52-3)
• EPA Substance Registry System: 3-DODECYLTHIOPHENE(104934-52-3)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 104934-52-3(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to yellow liquid

Uses

Different sources of media describe the Uses of 104934-52-3 differently. You can refer to the following data:
1. 3-Dodecylthiophene is a reactant used to make semiconducting copolymers.
2. Conducting polymer precursor.

Preparation

3-Dodecylthiophene can be prepared from 3-bromothiophene and halogenated hydrocarbons in one step. Steps: Under N2 atmosphere, slowly add 1-bromododecane (28.75g, 26.9 mL) to a 250mL three-necked flask containing a mixture of magnesium chips (3.28g, 0.135mol), anhydrous THF (30mL) and a small amount of iodine. mL, 0.13 mol) in dry THF (45 mL). After the mixture was refluxed at 70 °C for 2 hours, the system was cooled to room temperature with ice water, Ni(dppp)Cl2 (0.54 g, 1.00 mmol) was added first, and then 3-bromothiophene (16.31 g, 0.10 mol) was added slowly. Anhydrous THF (40 mL) solution. The mixed solution was stirred at room temperature overnight, and cold aqueous HCl (1.50 mol/L) was added to quench the reaction. The crude product was extracted with dichloromethane, dried over anhydrous magnesium sulfate, and further purified by column separation purification (n-hexane as eluent), resulting in a clear liquid (22.18 g, yield=88%).

General Description

3-Dodecylthiophene (3-DT) is a conjugating monomer that can be used as an active layer on semiconductors. It has good electronic properties and can be used in the development of p-type semiconducting polymers. It is mainly used in the formation of poly(3-dodecylthiophene) (P3DT) through electrochemical polymerization. P3DT can further be utilized for a variety of organic electronic based applications.

InChI:InChI=1/C16H28S/c1-2-3-4-5-6-7-8-9-10-11-12-16-13-14-17-15-16/h13-15H,2-12H2,1H3

Upstream product

• 872-31-1 3-Bromothiophene 
• 15890-72-9 laurylmagnesium bromide 
• 143-15-7 1-dodecylbromide 
• 869589-06-0 dodecylzinc(II) bromide 
• 4292-19-7 1-Iodododecane 
• 112-53-8 1-dodecyl alcohol 
• 905966-46-3 5,5-dimethyl-2-(thiophen-3-yl)-1,3,2-dioxaborinane 
• 112-52-7 1-chlorododecane 
• 10157-76-3 dodecyl 4-methylbenzenesulphonate 

Downstream Products

• 1007347-63-8 5,5'-bis(trimethylstannyl)-4,4'-bis(dodecyl)-2,2'-bithiophene 
• 1173788-58-3 2-(4-dodecylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 960524-18-9 2-(3-dodecylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 211181-63-4 (4-dodecylthiophen-2-yl)trimethylstannane 
• 1454583-77-7 C₆₄H₈₆O₆S₄ 
• 1454583-65-3 C₃₂H₄₄O₃S₂ 

Relevant articles and documents

Synthesis and Structural Characterization of Alkyl Oligothiophenes - The First Isomerically Pure Dialkylsexithiophene

Regioselective bromination of alkylated bi- and ter-thiophenes affords key building blocks for the synthesis of higher, isomerically pure alkyl oligothiophenes.For all new compounds, unequivocal structural assignment is based on a detailed analysis of the fully coupled 13C, 1H NMR spectra.

Design and synthesis of new ultra-low band gap thiadiazoloquinoxaline-based polymers for near-infrared organic photovoltaic application

Two D-A copolymers, F1 and F2, with fluorene and thiazole units were substituted, respectively, on a thiadiazoloquinoxaline (TDQ) unit to enhance the electron-accepting strength of TDQ. The copolymers were synthesized by a cross-coupling Stille reaction and their optical and electrochemical properties were examined, which revealed that they have ultra-low band gaps and absorption in the near-infrared. These copolymers were employed as donors along with PC71BM as an electron acceptor for the fabrication of solution-processed bulk heterojunction (BHJ) polymer solar cells. After the optimization of the donor-to-acceptor weight ratio and the solvent additive (4 v% DIO as solvent additive), devices with F1:PC71BM and F2:PC71BM displayed power conversion efficiencies (PCEs) of 5.80% and 3.32%, respectively. Although F2 possesses a broader absorption profile compared with F1, the lower value of PCE for the F2-based device was attributed to the low LUMO offset between F2 and PC71BM, which limited the exciton dissociation. The abovementioned results indicate that these copolymers can be utilized for ternary BHJ and tandem solar cells to achieve a high PCE.

Optical waveguide fabrication using a polymeric azine containing the 3-dodecyIthiophene moiety

New polymeric azines, DOZ and DOPh, containing the 3-dodecylthiophene moiety, have been obtained by the condensation reactions of 2,5-diformyl-3-dodecylthiophene with hydrazine and p-diaminobenzene, respectively. Their average molecular masses depend on t

Synthesis and characterization of acceptor-donor-acceptor-based low band gap small molecules containing benzoselenadiazole

Acceptor-donor-acceptor-type compounds 5′,5″-(benzo[c][1,2,5]selenadiazole-4,7-diyl)bis(3′-dodecyl-2,2′-bithiophene-5-carbonitrile) (9) and 4,4′-(5,5′-(benzo[c][1,2,5]selenadiazole-4,7-diyl)bis(3-dodecylthiophene-5,2-diyl))dibenzonitrile (10) were designed and synthesized. These compounds differ in terminal positions, compound 9 with a thiophene-containing nitrile group and compound 10 with a phenyl-containing nitrile group. Both compounds have shown good thermal stability and low band gap. The band gaps of compounds 9 and 10 were 1.74 and 1.83 eV, respectively. These results indicate that they are promising materials for use in optoelectronics.

Synthesis and characterization of low-band-gap poly(thienylenevinylene) derivatives for polymer solar cells

A series of conjugated polymers containing thienylenevinylene moieties as the electron donor for polymer solar cells were synthesized through Yamamoto and Stille coupling. The structure and device properties of the homopolymer (E)-poly[2,2′-(1,2-ethenediyl)bisthiophene] (PEBT), and two donor-acceptor-type copolymers (E)-poly[2,2′-(1,2-ethenediyl)bisthiophene- alt-4,7-(2,1,3-benzothiadiazole)] (PEBTBT) and (E)-poly[2,2′-(1,2- ethenediyl)bisthiophene-alt-5,5-(4′,7′-di-2-thienyl-2′, 1′,3′-benzothiadiazole)] (PEBTTBT) were investigated. The vinylene group inserted between two thiophene rings has an important role in lowering the band gap of thienylenevinylene derivatives. In addition, the donor-acceptor-type copolymers including a benzothiadiazole unit showed even lower band gap than their own homopolymer due to intramolecular charge transfer (ICT) through their conjugated backbones. As a result, PEBT, PEBTBT and PEBTTBT showed band gaps of 1.77, 1.37 and 1.57 eV, respectively. Bulk heterojunction photovoltaic devices were fabricated using blends of the polymers with [6,6]-phenyl C71-butyric acid methyl ester (PC70BM) and PEBTBT gave the best power conversion efficiency among them, at 1.07% under AM 1.5, 100 mW cm-2. The Royal Society of Chemistry 2011.

Thiophene-benzothiadiazole based donor–acceptor–donor (D-A-D) bolaamphiphiles, self-assembly and photophysical properties

Bolaamphiphilies with D-A-D type π-conjugated rigid cores composed by thiophenes as donors (D) and benzothiadiazole (BTD) as central acceptor (A) have been synthesised. Their self-assemblies and photophysical properties were investigated by polarising optical microscope, differential scanning calorimetry, X-ray diffraction and scanning electron microscopy. Such compounds can self-assemble into honeycomb cylinder mesophases with Colhex?/p6mm and Colsqu/p4mm lattices in their pure states as well as organogels with different morphologies in organic solvents. Their absorption spectra cover nearly the entire visible light range and their band gaps are relatively low. Tetrathiophene BTD based bolaamphilphiles (BT4/n) with higher D/A ratios than the bisthiophene BTD bolaamphilphiles (BT2/n) can self-assemble into more ordered nanostructures in both bulk states and solution. Both the absorption and emission peaks of BT4/n are strongly red shifted. The influence of the molecular conformation, the conjugated core length, as well as the D/A ratio on the self-assemble and photophysical characteristics of such D-A-D bolaamphiphiles are discussed.

Chemical synthesis and application research of cyanogroup containing functional material for modifying perovskite layer in perovskite solar cell

The invention aims at designing and synthesizing a cyanogroup compound and modifying a perovskite layer in a perovskite solar cell structure. According to an implementation method, a layer of modification material is arranged on the surface of perovskite in a spin coating manner, cyanogroups in material molecules and I in the perovskite structure interact, surface charges of the modification material are dispersed, meanwhile, I migration is reduced, and therefore the stability of the perovskite layer is improved; and benzene ring and alkyl chain components in the molecular structure can achieve the functions of improving interfacial compatibility and reducing the surface defects, and finally the aim of improving the performance of a perovskite solar cell is achieved. Ar in a chemical formula (1) (please see the specification) is a following aromatic compound (please see the specification). Ar in a chemical formula (2) (please see the specification) is a following aromatic compound (please see the specification). R1 is -CN or a chemical formula (please see the specification), and R2 is 1-16 alkyl chains.