4861-61-4

Usage

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

• 6790-19-8 1-thiopene-2-yl-dodecan-1-one 
• 26447-67-6 1-(thiophen-2-yl)hexan-1-one 
• 111-46-6 diethylene glycol 
• 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 
• 143-15-7 1-dodecylbromide 
• 112-16-3 n-dodecanoyl chloride 
• 188290-36-0 thiophene 
• 4292-19-7 1-Iodododecane 

Downstream Products

• 506-30-9 Arachidic acid 
• 1250377-33-3 naphthalene-2,7-diyl bis(4-(5-dodecylthiophene-2-carbonyloxy)benzoate) 
• 1258753-84-2 C₆₀H₇₀O₈S₂ 
• 1258753-92-2 C₅₄H₆₆O₈S₂ 
• 1258753-94-4 C₆₂H₇₀O₈S₄ 
• 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 
• 153561-79-6 5,5'''-didodecyl-2,2':5',2'':5'',2'''-quaterthiophene 
• 55373-89-2 methyl pentacosanoate 

Relevant academic research and scientific papers

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.

Biaxially Extended Conjugated Polymers with Thieno[3,2-b]thiophene Building Block for High Performance Field-Effect Transistor Applications

Biaxially thiophene side chain extended thieno[3,2-b]thiophene (TT2T)-based polymers, PTTT2T, P2TTT2T, PTTTT2T, and PTVTTT2T, were synthesized by Stille coupling polymerization with different conjugated moieties of thiophene (T), bithiophene (2T), thieno[3,2-b]thiophene (TT), and thiophene-vinylene-thiophene (TVT), respectively. The electronic properties of the prepared polymers could be effectively tuned because the variant π-conjugated building block affected the backbone conformation and the resulted morphology. The morphology of the thin films characterized by atomic force microscopy and grazing incidence X-ray diffraction showed that P2TTT2T and PTVTTT2T thin films possessed a better molecular packing with a nanofiber structure owing to their coplanar backbone. The average field-effect mobilities of PTTT2T, P2TTT2T, PTTTT2T, and PTVTTT2T were 6.7 × 10-6, 0.36, 2.2 × 10-3, and 0.64 cm2 V-1 s-1 (maximum 0.71), respectively, attributed to the coplanarity of polymer skeleton. In addition, the fabricated FET devices showed a high on/off ratio over 107 under ambient for over 3 months, suggesting the excellent environmental stability. The above results demonstrated that the biaxially extended fused thiophene based conjugated polymers could serve as a potential candidate for organic electronic device applications. (Graph Presented).

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.

Electrochemical deposition of highly-conducting metal dithiolene films

Electrochemical deposition has been used to prepare a thin film of neutral 4′,4-(3-alkyl)-thiophene-5′,5-hydogen-nickel and copper dithiolenes (Ni-C2, Cu-C2). The application of molecular electrodeposition provides a means to solution process molecular semiconductors of poor solubility, which results from the strong intermolecular interaction required for charge transport. Both Ni-C2 and Cu-C2 form continuous thin films that show intense NIR absorptions, extending to 1800 nm and 2000 nm respectively giving evidence for the strong intermolecular interactions in the solid state. Both films are highly conducting and temperature dependence of resistance gave an activation energy of 0.42 eV and 0.072 eV respectively, with the near-metallic behaviour of Cu-C2 attributed to the additional presence of an unpaired electron.

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.

Design, synthesis, and characterization of α,ω-disubstituted indeno[1,2-b]fluorene-6,12-dione-thiophene molecular semiconductors. Enhancement of ambipolar charge transport through synthetic tailoring of alkyl substituents

A series of indeno[1,2-b]fluorene-6,12-dione-thiophene derivatives with hydrocarbon substituents at α,ω-positions as side groups have been designed and synthesized. The new compounds were fully characterized by 1H/13C NMR, mass spectrometry, cyclic voltammetry, UV-vis absorption spectroscopy, differential scanning calorimetry, thermogravimetric analysis, and melting point measurements. The solid state structure of the indeno[1,2-b]fluorene-6,12-dione acceptor core has been identified based on single-crystal X-ray diffraction (XRD). The structural and electronic properties were also studied using density functional theory calculations, which were found to be in excellent agreement with the experimental findings and provided further insight. The detailed effects of alkyl chain size and orientation on the optoelectronic properties, intermolecular cohesive forces, thin-film microstructures, and charge transport performance of the new semiconductors were investigated. Two of the new solution-processable semiconductors, 2EH-TIFDKT and 2OD-TIFDKT, were deposited as thin-films via solution-shearing, drop-casting, and droplet-pinned crystallization methods, and their morphologies and microstructures were investigated by X-ray diffraction (XRD) and atomic force microscopy (AFM). The solution-processed thin-film transistors based on 2EH-TIFDKT and 2OD-TIFDKT showed ambipolar device operations with electron and hole mobilities as high as 0.12 cm2 V-1 s-1 and 0.02 cm2 V-1 s-1, respectively, with Ion/Ioff ratios of 105 to 106. Here, we demonstrate that rational repositioning of the β-substituents to molecular termini greatly benefits the π-core planarity while maintaining a good solubility, and results in favorable structural and optoelectronic characteristics for more efficient charge-transport in the solid-state. The ambipolar charge carrier mobilities were increased by two-three orders of magnitude in the new indeno[1,2-b]fluorene-6,12-dione-thiophene core on account of the rational side-chain engineering.

Semiconducting Compounds and Related Compositions and Devices

Disclosed are new semiconductor materials prepared from thienocoronene-based compounds and related heteroaromatic analogs. Such compounds can exhibit high carrier mobility and/or good current modulation characteristics. In addition, the compounds of the present teachings can possess certain processing advantages such as solution-processability and/or good stability at ambient conditions.

Synthesis and optical properties of pyrrolo[3,2-b ]pyrrole-2,5(1 H,4 H)-dione (iDPP)-based molecules

We describe the synthesis and photophysical properties of a series of derivatives of pyrrolo[3,2-b]pyrrole-2,5(1H,4H)-dione-3,6-diyl (iDPP) linked to two oligothiophenes of variable length (nT). The iso-DPP-oligothiophenes (iDPPnTs) differ from the common

A first synthesis and physical properties of asymmetric anthracenes-thiophenes bridged with ethylene

Here we report our recent result of a new semiconductor material, which has an asymmetric structure. The synthesized molecules consist of anthracene and thiophene connected by bridged ethylene and substituted with hexyl or dodecyl groups as pendants. The semiconductors were synthesized using a McMurry coupling reaction between anthracene-2-carbaldehyde and corresponding 5-hexyl(or dodecyl)thiophene-2-carbaldehyde. A first investigation of synthesized asymmetry AVHT (9a) and AVDT (9b) for the physical properties showed that they have high oxidation potential and thermal stability. The devices prepared by using AVHT (9a) and AVDT (9b) showed the mobility of 2.6 × 10-2 cm 2/Vs and 4.4 × 10-3 cm2/Vs, respectively, in solution processed OTFTs.

Synthesis and mesophase behavior of phenylthiophene based amphiphilic molecules

Novel amphiphilic molecules consisting of a rigid 2-phenylthiophene core, with a polar flexible tri(oxylethylene) moiety attached to the phenyl ring and one or two alkyl chains attached to the thiophene ring at the other side have been synthesized by using Ni(II) and Pd(0) catalyzed coupling reaction as key steps. The tri(oxylethylene) moieties were terminated with hydroxyl group, sodium carboxylate group and lithium carboxylate group respectively. The thermotropic and solvent induced liquid crystalline behavior of these substances was investigated by polarized optical microscopy, differential scanning calorimetry and X-ray diffraction. Thereby the influence of the terminal groups attached to the tri(oxylethylene) moities as well as the influence of the length and the number of the alkyl chains on the mesophase behavior were investigated. The single alkyl chain Na-carboxylate termianted derivatives show smectic A phases, double alkyl chain Na-carboxylate terminated derivatives show a thermo tropic hexagonal columnar mesophase, while columnar mesophases are found in both single and double alkyl chain Li-carbonate terminated derivatives. The model for molecular organization in the hexagonal columnar mesophase is established.