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

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

Uses

Used in Organic Electronics Industry:
3-Dodecylthiophene is used as a conducting polymer precursor for the synthesis of P3DT, which is an essential material in the development of various organic electronic applications.
Used in Semiconductors:
3-Dodecylthiophene is used as an active layer on semiconductors, contributing to the enhancement of electronic properties and performance in electronic devices.
Used in Electrochemical Polymerization:
3-Dodecylthiophene is used as a monomer in the electrochemical polymerization process to form P3DT, which can be further utilized in a variety of organic electronic-based applications.

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%).

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 
• 905966-46-3 5,5-dimethyl-2-(thiophen-3-yl)-1,3,2-dioxaborinane 
• 10157-76-3 dodecyl 4-methylbenzenesulphonate 
• 112-52-7 1-chlorododecane 
• 112-53-8 1-dodecyl alcohol 
• 4292-19-7 1-Iodododecane 
• 869589-06-0 dodecylzinc(II) bromide 

Downstream Products

• 148256-63-7 3-n-dodecyl-2,5-dibromothiophene 
• 139100-06-4 2-bromo-3-dodecylthiophene 
• 350499-09-1 5'-bromo-4'-dodecyl-3-phenyl-[2,2']-bithiophene 
• 1170871-42-7 3-dodecyl-2-phenylthiophene 
• 1245707-29-2 1,4-bis((E)-2-(5-bromo-3-dodecylthiophen-2-yl)vinyl)benzene 
• 1299469-86-5 C₂₃H₃₃BrOS 
• 1299469-91-2 C₃₅H₅₈OS 
• 1007347-63-8 5,5'-bis(trimethylstannyl)-4,4'-bis(dodecyl)-2,2'-bithiophene 
• 1454583-89-1 C₅₈H₇₈O₆S₄ 
• 1454583-65-3 C₃₂H₄₄O₃S₂ 
• 1454583-77-7 C₆₄H₈₆O₆S₄ 
• 1173788-58-3 2-(4-dodecylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 211181-63-4 (4-dodecylthiophen-2-yl)trimethylstannane 

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.

Structural Insight into Aggregation and Orientation of TPD-Based Conjugated Polymers for Efficient Charge-Transporting Properties

In this study, we obtained a new structural insight into the charge-transporting properties in TPD-based polymers that cannot be solely explained in terms of the type of orientation. We synthesized two types of copolymers comprising mono-TPD or bis-TPD as the accepting unit. Although the planarity and energy levels are similar with the mono-TPD unit, the aggregation state is quite different, and the X-aggregation tendency seems to be stronger when the bis-TPD unit is incorporated. In the case of TPD1, an effective π-πorbital overlap is found to originate from the H-aggregates, and 3D charge transport pathways are formed with a bimodal orientation of edge-on and face-on, resulting in an efficient charge transportation (1.84 cm2·V-1·s-1 of hole and 0.31 cm2·V-1·s-1 of electron). In contrast, despite the well-aligned edge-on orientation of TPD2, it exhibited a relatively very low mobility and splitted emission characteristics in photoluminescence spectra because of the tilted intermolecular stacking pattern with an X-shape (0.015 cm2·V-1·s-1 for hole and 0.16 cm2·V-1·s-1 for electron). An overall characterization of the semiconducting polymers was performed, and it was found that the type of aggregation in the final thin films, such as H- or X-aggregation, is indeed important and perhaps more important than the orientation to obtain polymers with a high charge carrier mobility.

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.

Intermolecular Arrangement of Fullerene Acceptors Proximal to Semiconducting Polymers in Mixed Bulk Heterojunctions

Precise control of the molecular arrangements at the interface between the electron donor and acceptor in mixed bulk heterojunctions (BHJs) remains challenging, despite the correlation between structural characteristics and efficiency in organic photovoltaics (OPVs). This study reveals that the substitution patterns of linear and branched alkyl side chains on electron-donating/-accepting alternating copolymers can control the positions of an acceptor molecule (C60) around the π-conjugated main chains in mixed BHJs. Two-dimensional solid-state NMR demonstrates a marked difference in the location of C60 in the blend films. A copolymer with an electron-accepting unit positioned in close proximity to C60 demonstrated higher OPV performance in combination with various fullerene derivatives. This molecular design offers precise control over the interfacial molecular structure, thereby paving the way for overcoming the current limitations of OPVs comprising mixed BHJs.

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 of poly(3-dodecyl-2,5-thienylene vinylene) by solid-state metathesis polycondensation

The synthesis of poly(thienylene vinylenes) (PTV) has been attracting attention due to the low band gaps and high electrical conductivities of these materials, making them applicable for charge storage devices, transparent conductive coatings, and electrochromic devices. Unsubstituted PTV is an intractable polymer that is usually synthesized via a processable precursor. This article reports the synthesis of conjugated polymers using solid-state metathesis conditions, demonstrating the efficiency of this methodology for preparation of a processable polymer, such a 3-dodecyl PTV (P3DDTV). The 3-dodecyl-2,5-dipropenylthiophene was synthesized and subsequently polymerized using ADMET conditions with Grubbs' second-generation catalyst. The prepolymer film (Mn = 4000 g/mol) was further polymerized in the solid state to give a final product with Mn = 14 000 g/mol (a 3.5-fold increase while in the solid state). The polymer obtained by this methodology exhibited thermal (Tg = 43 °C and Tm = 115 °C) and electrochemical (optical band gap of 1.65 eV and HOMO energy level of 5.35 eV) properties similar to those of PTV polymers synthesized by ADMET polymerization using a high boiling solvent or by cross-coupling reactions.

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 a poly(1,3-dithienylisothianaphthene) derivative for bulk heterojunction photovoltaic cells

The synthesis of a poly(1,3-dithienylisothianaphthene) (PDTITN) derivative obtained via oxidative polymerization of 5,6-dichloro-l,2-bis(3a?2-dodecylthienyl)isothianaphthene is described. PDTITN exhibits a band gap of 1.80-1.85 eV. The redox properties of PDTITN were characterized using cyclic voltammetry and spectroelectrochemisty. Photoexcitation of PDTITN results in photoluminescence (PL) in the near-IR region and the formation of a triplet state. In the presence of a methanofullerene (PCBM) as an electron acceptor, PL and triplet formation of PDTITN are quenched. In photovoltaic devices using blends of the polymer with PCBM, the observed incident-photon-to-collected-electron efficiency (IPCE) up to 24% at 400 nm and the 3 orders of magnitude increase of short circuit current as compared to the polymer alone prove the photoactivity of the PDTITN/PCBM blend in the device.

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.

Synthesis of donor-acceptor copolymer using benzoselenadiazole as acceptor for OTFT

Donor-acceptor-based poly(E)-4-(3,4′-didodecyl-5′-(2-(3-dodecylthiophen-2-yl)vinyl)-2,2′-bithiophen-5-yl)-7-(4-dodecylthiophen-2-yl)benzo[c][1,2,5]selenadiazole (11) has been synthesized by a Stille coupling reaction. This polymer has a low energy band gap between the HOMO and LUMO energy levels of 1.75 eV. The polymer exhibited good thermal stability. An OTFT prepared using this polymer displayed high hole mobility of 0.097 cm2 V-1 s-1 at 200°C, a high on/off ratio of 7.8 × 104, and a low threshold voltage of 11.2 V. When compared with as-cast films, annealed films exhibited higher mobility, which was attributed to an increase in crystallinity with an increase in the annealing temperature.