16900-51-9

Usage

Uses

Used in Optoelectronic Devices:
1,4-Di-(2-thienyl)-1,3-butadiyne is used as a component in optoelectronic devices for its π-conjugated system, which contributes to its electronic and optical properties, making it suitable for applications in this industry.
Used in Organic Photovoltaics:
In the field of organic photovoltaics, 1,4-Di-(2-thienyl)-1,3-butadiyne is used as a material with potential to enhance the performance of solar cells due to its π-conjugated system and unique properties.
Used in Molecular Electronics:
1,4-Di-(2-thienyl)-1,3-butadiyne is utilized as a component in molecular electronics for its electronic properties, which can be harnessed to create devices at the molecular scale.
Used in Organic Light-Emitting Diodes (OLEDs):
In the industry of organic light-emitting diodes, 1,4-Di-(2-thienyl)-1,3-butadiyne is used as a material to improve the efficiency and performance of OLEDs, taking advantage of its optical properties.
Used in Organic Field-Effect Transistors (OFETs):
1,4-Di-(2-thienyl)-1,3-butadiyne is employed as a material in organic field-effect transistors for its electronic properties, which can be beneficial in the development of flexible and low-cost electronic devices.
Used in Organic Photonic Devices:
In the field of organic photonics, 1,4-Di-(2-thienyl)-1,3-butadiyne is used as a component for its optical properties, which can be applied to create devices that manipulate and control light at the molecular level.

Upstream product

• 4298-52-6 2-ethynyl-thiophene 
• 113705-19-4 2,5-diethynyl-3,4-bis(3-hydroxy-3-methyl-1-butynyl)thiophene 
• 1003-09-4 2-bromothiophene 
• 5929-72-6 2,7-dimethyl-octa-3,5-diyne-2,7-diol 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 77295-66-0 2-(2,2-dibromovinyl)thiophene 
• 3437-95-4 2-Iodothiophene 
• 1066-54-2 trimethylsilylacetylene 
• 4843-44-1 (2-thienyl)propiolic acid 
• 88-15-3 2-Acetylthiophene 
• 768-60-5 4-methoxyphenylacetylen 
• 40231-03-6 2-(trimethylsilylethynyl)thiophene 
• 827-15-6 1,2,3,4,5-pentafluoro-6-iodobenzene 

Downstream Products

• 1081-34-1 2,2':5',2''-terthiophene 
• 17284-08-1 (Z,Z)-1,4-di(benzylthio)-1,4-di(2-thienyl)-1,3-butadienyl 
• 1426938-87-5 2,5-bis(2-thienyl)-3-(triisopropylsilyl)thiophene 
• 88089-34-3 2,5-bis(thiophen-2-yl)furan 
• 51678-15-0 2,5-di(thiophen-2-yl)selenophene 
• 1187162-51-1 C₂₂H₁₈N₂OS₂ 

Relevant academic research and scientific papers

Unusually sluggish copper(I)catalyzed oxidative dimerization of 2-ethynyl-1-methylpyrrole

Reaction of 2-ethynyl-1-methylpyrrole with oxygen in the presence of catalytic amounts of copper(I)chloride proceeds only upon addition of 1,8-diazabicycloundec-7-ene (DBU).

Stabilized Cu/Cu2O nanoparticles on rGO as an efficient heterogeneous catalyst for Glaser homo-coupling

Stabilized Cu/Cu2O nanoparticles on reduced graphene oxide (Cu/Cu2O-NPs@rGO) was synthesized by one-step co-reduction and acted as a green and efficient non-noble metal heterogeneous catalyst for Glaser homo-coupling. Through the synergic catalytic effect of Cu/Cu2O nanoparticles and graphene, the heterogeneous hybrid nanoparticles catalyst showed excellent catalytic performance for Glaser homo-coupling with the yield up to 99% of 1,4-diphenyl buta-1,3-diyne. And excellent functional group tolerance was obtained with oxygen as a green oxidant. Furthermore, the catalyst can be easily separated and recycled seven times without significant decline in its catalytic performance.

A convenient synthesis of aromatic-ring-substituted diacetylenes

A simple and convenient way for the preparation of symmetrical diarylbutadiynes 5 with improved yields is reported (Scheme2). The reaction time is drastically reduced using this method compared to previously reported procedures.

Copper(II) chloride-catalyzed Glaser oxidative coupling reaction in polyethylene glycol

Polyethylene glycol was shown to be an environmentally benign reaction medium for the copper(II) salt -catalyzed Glaser coupling reaction of terminal alkynes. In particular, oxygen as the sole oxidant worked very well for arylacetylenes even in short reaction time. The product was easily separated by extraction and the catalytic system could be reused four times without significant loss of reactivity.

The Unprecedented cobalt-catalysed oxidative glaser coupling under reductive conditions

The cobalt-catalysed Glaser-type coupling of terminal alkynes was achieved utilising nitrobenzene as a stoichiometric oxidising agent under reductive conditions. The proposed electron transfer from zinc powder to a nitrobenzene coordinated to the cobalt centre initiates the coupling of the coordinated alkynes. Other aryl-, alkenyl-, alkyl-, and silylacetylenes besides phenylacetylene could also be coupled to generate the 1,3-diynes in moderate to very good yields. Georg Thieme Verlag Stuttgart.

CuCl-catalyzed green oxidative alkyne homocoupling without palladium, ligands and bases

CuCl-catalyzed green oxidative homocoupling of terminal alkynes produces symmetrical 1,4-disubstituted 1,3-diynes in good to excellent yields, using air as an environmentally friendly oxidant and the occurrence of water as exclusive byproduct in the whole process, and eliminating the need for ligands, bases, oxidants and expensive palladium catalysts. The Royal Society of Chemistry.

Importance of bases on the copper-catalyzed oxidative homocoupling of terminal alkynes to 1,4-disubstituted 1,3-diynes

Copper-catalyzed, solvent-free oxidative homocoupling of terminal alkynes can be performed to 1,3-diynes in good to excellent yields in the absence of any additives, using air as environmentally friendly oxidant and the occurrence of water as an exclusive byproduct in the whole process. It is shown that AcO - of copper (II) acetate catalyst may take the role of base and found that the homocoupling cannot occur using weakly basic copper salt catalysts such as CuBr, CuCl, or CuI. Thus, the bases are absolutely necessary in the process of the homocoupling of terminal alkynes. 2012 Elsevier Ltd. All rights reserved.

Synthesis and properties of 1,1′-bis(diacetylene-group) connected ferrocene-thiophene derivative: A cooperatively functional behavior of diacetylene-group connected constituents

An extended π-electronic conjugation system of 1,1′- bis(diacetylene-group) connected ferrocene-thiophene derivative has been synthesized, with our integrated reaction between the corresponding TMS-protected acetylenes in one-pot. Its electronic properties have been examined, suggesting a cooperatively functional behavior of the diacetylene-group connected constituents.

Evidence of a Photoinduced Electron-Transfer Mechanism in the Fluorescence Self-quenching of 2,5-Substituted Selenophenes Prepared through in Situ Reduction of Elemental Selenium in Superbasic Media

A series of new 2,5-disubstituted selenophene derivatives are described from elemental selenium and 1,3-diynes in superbasic media. The activation of elemental selenium in a KOH/DMSO system allows cyclization with conjugated diynes at room temperature. The cyclization reaction is extended to a broad range of functional groups, for which photophysics were experimentally and theoretically investigated. The selenophene derivatives present absorption maxima in the UV-A region and fluorescence emission in the violet-to-blue region. Fluorescence decay profiles were obtained showing a monoexponential decay with fast fluorescence lifetimes (～0.118 ns), as predicted by the Strickler-Berg relations. In general, in both investigations, no dependence on the solvent polarity on the absorption and emission maxima location was observed. On the other hand, solvents and substituents are shown to play a role in the fluorescence quantum yield values. In addition, a fluorescence self-quenching behavior could be observed, related to a photoinduced electron-transfer mechanism. Theoretical calculations performed at the MP2/ADC(2)/cc-pVDZ level of theory were performed in order to investigate the photophysical features of this series of selenophene derivatives.

Synthesis of 1,3-Diynes Using Calcium Carbide as an Alkyne Source

A simple method for the synthesis of 1,3-diynes from iodoarenes using calcium carbide as an alkyne source and air as an oxidant is described. A series of 1,4-diarylbuta-1,3-diynes were efficiently synthesized by this strategy. The salient features of this protocol are the use of inexpensive and easy-to-handle alkyne source, broad substrate scope, open-air condition, and simple operation procedure.