24769-39-9

Upstream product

• 79852-24-7 2-Decanoylthiophene 
• 188290-36-0 thiophene 
• 112-29-8 1-bromo dodecane 
• 2050-77-3 Iododecane 
• 112-13-0 n-decanoyl chloride 
• 30089-00-0 9-octyl-9-bora-bicyclo[3.3.1]nonane 
• 92138-63-1 1-iodo-2-(thien-2-yl)ethane 
• 872-05-9 1-Decene 
• 109-72-8 n-butyllithium 
• 1003-09-4 2-bromothiophene 

Downstream Products

• 514188-72-8 2-bromo-5-decylthiophene 
• 188917-80-8 5-decyl-2,2':5',2''-terthiophene 
• 3133-01-5 1-tricosanol 
• 2433-97-8 tricosanoic acid methyl ester 
• 103050-32-4 5-(5-decyl-[2]thienyl)-5-(2,4-dinitro-phenylhydrazono)-valeric acid ethyl ester 
• 1002-84-2 palmitic acid 

Relevant academic research and scientific papers

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.

From Dimethylamine to Pyrrolidine: The Development of an Improved Nickel Pincer Complex for Cross-Coupling of Nonactivated Secondary Alkyl Halides

Replacement of a dimethyl amino group of the amidobis(amine) nickel(II) pincer complex (1), [(MeN2N)Ni-Cl], by a pyrrolidino group resulted in a new nickel(II) pincer complex (2), [(PyrNMeNN)Ni-Cl]. Complex 2 is an efficient catalyst for Kumada and Suzuki-Miyaura cross-coupling of nonactivated secondary alkyl halides, while complex 1 is largely inactive. The significant activity difference is tentatively attributed to a minimal structural difference, which leads to a more hemilabile ligand.

Anti-Markovnikov Hydroheteroarylation of Unactivated Alkenes with Indoles, Pyrroles, Benzofurans, and Furans Catalyzed by a Nickel-N-Heterocyclic Carbene System

We report the catalytic addition of C-H bonds at the C2 position of heteroarenes, including pyrroles, indoles, benzofurans, and furans, to unactivated terminal and internal alkenes. The reaction is catalyzed by a combination of Ni(COD)2 and a sterically hindered, electron-rich N-heterocyclic carbene ligand or its analogous Ni(NHC)(arene) complex. The reaction is highly selective for anti-Markovnikov addition to α-olefins, as well as for the formation of linear alkylheteroarenes from internal alkenes. The reaction occurs with substrates containing ketones, esters, amides, boronate esters, silyl ethers, sulfonamides, acetals, and free amines.

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.

Use of compounds comprising a piperazine structural element in organic electronic devices and compounds and polymers comprising a piperazine structural element

Use of compounds comprising at least one of structural elements (1) to (5) or of oligomers or polymers comprising units obtained from compounds of formulas (1) to (5 as organic semiconductors in organic electronic devices.

Organic semiconductor material, organic semiconductor structure and organic semiconductor apparatus

The present invention is directed to the provision of a novel liquid crystalline organic semiconductor material that is highly stable under an film forming environment and, at the same time, can easily form a film, for example, by coating. The liquid crystalline organic semiconductor material is represented by chemical formula 1 wherein R1 and R2 represent an identical alkyl group having 7 to 20 carbon atoms: There is also provided a liquid crystalline organic semiconductor material characterized by being represented by chemical formula 2 wherein R3 and R4 represent an identical alkyl group having 7 to 20 carbon atoms:

Photochromism of 1,2-bis(2-n-alkyl-5-formyl-3-thienyl)perfluorocyclopentene derivatives

Photochromic diarylethene derivatives 1o-6o bearing long alkyl chains (≥seven carbon atoms) have been synthesized and their structures with the exception of compound 3o have been determined by single-crystal X-ray diffraction analysis. The effect of alkyl chain length on their properties, including photochromism both in solution and in PMMA film and their electrochemical properties were investigated in detail. All of these diarylethenes showed good photochromism both in solution and in PMMA film. The diarylethene derivatives with n-heptyl and n-octyl substituents at the 2-positions of the two thiophene rings exhibit photochromism even in the single-crystalline phase, but those with n-decyl, n-undecyl and n-dodecyl groups showed no photochromism in the single-crystalline phase. Compared to the photochromic features of 1,2-bis(2-methyl-5-formyl-3-thienyl)perfluorocyclopentene, introduction of the long alkyl groups was found to decrease the cycloreversion quantum yield and induce bathochromic shifts of the absorption spectra of the closed-ring isomers. The absorption coefficients of both open- and closed-ring isomers increased remarkably when replacing the methyl groups at 2-positions of the two thiophene rings with n-heptyl ones. However, further increase was not observed the alkyl chain becoming longer from n-heptyl to n-dodecyl groups. The cyclic voltammetry indicated that the HOMO and LUMO energy levels of these diarylethenes increased with the increase of the carbon numbers of alkyl chains from n-heptyl to n-dodecyl groups, but their band gaps were essentially not influenced by the alkyl chain length.

Large area liquid crystal monodomain field-effect transistors

Butyl, hexyl, and decyl derivatives of the liquid-crystalline organic semiconductor 5,5″-bis(5-alkyl-2-thienylethynyl)-2,2′:5′, 2″-terthiophene were synthesized and studied with respect to their structural, optical, and electrical properties. By means of an optimized thermal annealing scheme the hexyl and decyl compounds could be processed into self-assembled monodomain films of up to 150 mm in diameter. These were investigated with X-ray diffractometry, which revealed a clearly single-crystalline monoclinic morphology with lamellae parallel to the substrate. Within the lamellae the molecules were found to arrange with a tilt of about 50° with the rubbing direction of the polyimide alignment layer. The resulting, close side-to-side packing was confirmed by measurements of the UV/vis absorption, which showed a dichroic ratio of 19 and indicated H-aggregation. AFM analyses revealed self-affinity in the surface roughness of the monodomain. The compounds showed bipolar charge transport in TOF measurements, with hole mobilities reaching up to 0.02 cm2/Vs and maximum electron mobilities around 0.002 cm2/Vs. The hexyl derivative was processed into large-area monodomain top-gate field-effect transistors, which were stable for months and showed anisotropic hole mobilities of up to 0.02 cm2/Vs. Compared to multidomain bottom-gate transistors the monodomain formation allowed for a mobility increase by 1 order of magnitude.

Synthesis and thermal behaviour of α,α′-didecyloligothiophenes

α,α′-Didecylquater-, -quinque- and -sexi-thiophenes were synthesized by Kumada cross-coupling and oxidative coupling reactions. For the former reaction Pd(dppf)Cl2 was found to be a more efficient catalyst than the usually applied Ni(dppp)Cl2. Thermal behaviour of all new oligothiophenes was investigated by differential scanning calorimetry and polarizing optical microscopy. It was shown that all these compounds possess not only crystal phases but also high temperature ordered smectic mesophases and that the clearing point increases linearly with the number of conjugated thiophene rings. A degree of order in the crystal phase was estimated on the basis of thermodynamic data. The highest degree of order was proposed for α,α′-didecylquaterthiophene, which explains why the mobility of end-α,α′-capped quaterthiophenes in FET (field effect transistor) devices is comparable or sometimes better than those of corresponding quinque- and sexi-thiophene derivatives.

The synthesis and characterisation of novel thienyl-pyrimidine liquid crystalline materials

The synthesis and transition temperatures of a series of novel thienyl-pyrimidine liquid crystalline materials is described. Palladium catalysed coupling of 5-n-alkyl-2-tri-n-butylstannyl thiophenes to 5-bromo-2-iodopyrimidine is used to create novel pyrimidine compounds which exhibit lower melting points than similar pyrimidine liquid crystals. These compounds exhibit a variety of phases including smectic A, C, G, B and hexstatic B also they exhibit several as yet unidentifiable phases. Speculation as to hydrogen bonding in the liquid crystalline core is also discussed therein.