1268060-76-9

Usage

Uses

Used in Organic Electronics:
3-(2-Octyl-dodecyl)-thiophene is used as a component in the development of organic semiconductors due to its electrical conductivity and film-forming properties. It contributes to the advancement of electronic devices such as light-emitting diodes and solar cells, enhancing their performance and efficiency.
Used in Polymer Chemistry:
In the field of polymer chemistry, 3-(2-Octyl-dodecyl)-thiophene is utilized as a building block for the synthesis of novel polymers with tailored properties. Its incorporation into polymer structures can improve their electrical conductivity, stability, and compatibility with other materials.
Used as a Surfactant:
The long alkyl chain of 3-(2-Octyl-dodecyl)-thiophene makes it suitable for use as a surfactant in various applications. It can improve the solubility of other compounds in non-polar solvents, facilitating processes in industries such as pharmaceuticals, cosmetics, and chemical manufacturing.
Used in Materials Science:
3-(2-Octyl-dodecyl)-thiophene's versatility extends to the field of materials science, where it can be employed in the design and synthesis of new materials with unique properties. Its ability to form stable thin films and its compatibility with other materials make it a valuable component in the development of advanced materials for various applications.

Upstream product

• 872-31-1 3-Bromothiophene 
• 1043023-53-5 9-(iodomethyl)nonadecane 
• 13893-37-3 2-octydodecyl aldehyde 
• 5333-42-6 2-octyldodecan-1-ol 
• 69620-20-8 9-(bromomethyl)nonadecane 

Downstream Products

• 1268060-77-0 2-bromo-3-(2-octyldodecyl)thiophene 

Relevant academic research and scientific papers

Synthesis and characterization of two fluorenone-based conjugated polymers and their application in solar cells and thin film transistors

Two new fluorenone-based conjugated polymers, F1 and F2, were synthesized via the Stille cross-coupling polymerization. Spectral measurements showed that both polymers had optical band gaps of 1.99 eV and 1.89 eV, respectively, calculated based on the film onset absorption edge. Cyclic voltammetric studies gave HOMO/LUMO energy levels of -5.18 eV/-3.19 eV and -5.40 eV/-3.51 eV, respectively, and the polymers were thermally stable at temperatures over 300 °C. Organic field-effect transistor and bulk-heterojunction solar cell performance characteristics of both polymers as p-type semiconductors were evaluated.

A fluorine-induced high-performance narrow bandgap polymer based on thiadiazolo[3,4-: C] pyridine for photovoltaic applications

Thiadiazolo[3,4-c]pyridine (PT) has great potential in the construction of high-performance narrow bandgap (NBG) photovoltaic polymers. But to date the best power conversion efficiencies (PCEs) for PT-containing polymers are only around 6%. Herein, we report two PT-containing NBG polymers PDTPT-2T and PDTPT-2TF based on 2,2′-bithiophene (2T) and 3,3′-difluoro-2,2′-bithiophene (2TF), respectively. The effects of a fluorine substituent on optoelectronic properties are thoroughly investigated. The film absorption onset of PDTPT-2TF is 855 nm, bathochromic-shifted by 24 nm in comparison with that (831 nm) of PDTPT-2T. The lowest unoccupied molecular orbital (LUMO) and highest occupied molecular orbital (HOMO) energy levels of PDTPT-2TF are down-shifted by 0.15 and 0.11 eV relative to those of PDTPT-2T, respectively. X-ray diffraction (XRD) patterns indicate that a more ordered structure is formed in the solid film of PDTPT-2TF. Furthermore, the miscibility between the polymer and [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) is significantly improved through the introduction of fluorine. Consequently, PDTPT-2TF exhibits a high PCE of 8.01%, while PDTPT-2T only shows a maximum PCE of 2.65%. The efficiency of 8.01% is the highest one for PT-containing polymers, and more importantly, it is achieved without any processing additives or post-treatments. This work indicates that PT would have great potential as a building block to construct high-performance photovoltaic polymers.

C(SP3)-C(SP2) CROSS-COUPLING REACTION OF ORGANOZINC REAGENTS AND HETEROCYCLIC (PSEUDO)HALIDES

Provided is a method of synthesizing a C(sp3)-C(sp2) cross-coupled compound comprising reacting a C(sp3) coupling partner with a C(sp2) coupling partner, a catalyst, and a solvent; wherein the C(sp3) coupling partner comprises an organic zinc reagent; and wherein the C(sp2) coupling partner comprises a heterocyclic halide or a heterocyclic pseudo halide. The method further comprises synthesis of the organic zinc reagent, wherein the synthesis comprises reacting a zinc powder with an acid, filtering, washing, and drying to obtain an activated zinc powder; and reacting the activated zinc powder with a metal iodide catalyst and a second solvent and heating for a predetermined time to obtain the organic zinc reagent.

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.

Cobalt-Catalyzed Reductive Alkylation of Heteroaryl Bromides: One-Pot Access to Alkylthiophenes, -furans, -selenophenes, and -pyrroles

A practical and convenient Co-catalyzed alkylation method for the facile introduction of various alkyl chains into organic electronically significant heteroaryl compounds, including thiophenes, furans, selenophenes, and pyrroles, is reported. Under well-optimized reaction conditions, a wide range of alkylated heteroaryl compounds have beeen efficiently prepared in moderate to good isolated yields. Notably, 2- or 3-alkylthiophenes, which play a decisive role in polymer chemistry and organic materials, have been synthesized step-economically for the first time by this reductive-coupling methodology using inexpensive cobalt salts as catalysts. This straightforward synthetic procedure avoids the preparation of moisture-unstable organometallic reagents (RMgX or RZnX) required in conventional alkylation protocols. Various alkyl chains have been introduced into organic, electronically important heteroaryl compounds step-economically through Co-catalyzed reductive alkylation reactions. The resulting alkylheteroarenes are indispensable building blocks for polymer chemistry and π-functional organic materials.

Synthesis and optical properties of photovoltaic materials based on the ambipolar dithienonaphthothiadiazole unit

Dithieno[3′2′:5,6;2′′,3′′:7,8]naphtho[2,3-c][1,2,5]thiadiazole (DTNT) was designed to control the band energies of the polymers for photovoltaic materials. Electrochemical analysis showed that DTNT acts as both an electron donor and an electron acceptor, revealing the ambipolar nature of the DTNT unit. The direct arylation polymerization of DTNT with 2,2′-bithiophene (BTh) and 3,6-bis(2-thienyl)pyrrolo[3,4-c]pyrrole-1,4-dione (DPP) afforded four polymers that differed in either the unit of copolymerization or the chosen side chains. In the PDTNT-BTh series, a shoulder absorption band was observed at a longer wavelength than the intense absorption band. The PDTNT-DPP series exhibited a narrow band gap of less than 1.4 eV and a low HOMO energy of -5.43 eV. An organic photovoltaic cell that contained a PDTNT-BTh polymer with 2-ethylhexyl groups and [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) as an active layer afforded the best performance among the studied compounds, with a JSC of 6.98 mA cm-3, a VOC of 0.758 V, a FF of 0.52, and a PCE of 2.76%.