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Upstream product

• 1003-09-4 2-bromothiophene 
• 3972-65-4 1-bromo-4-tert-butylbenzene 
• 188290-36-0 thiophene 
• 15106-95-3 bis(thien-2-yl)zinc 
• 343604-17-1 5-(4-(tert-butyl)phenyl)thiophene-2-carbaldehyde 
• 5713-61-1 thiophen-2-yl magnesium bromide 
• 52436-75-6 (4-tert-butylphenyl)diazonium tetrafluoroborate 
• 123324-71-0 p-tert-butylphenylboronic acid 
• 96-43-5 2-thienyl chloride 

Relevant academic research and scientific papers

Impact of terminal substituents on the electronic, vibrational and optical properties of thiophene-phenylene co-oligomers

Owing to the combination of efficient charge transport and bright luminescence, thiophene-phenylene co-oligomers (TPCOs) are promising materials for organic light-emitting devices such as diodes, transistors and lasers. The synthetic flexibility of TPCOs enables facile tuning of their properties. In this study, we address the effect of various electron-donating and electron-withdrawing symmetric terminal substituents (fluorine, methyl, trifluoromethyl, methoxy, tert-butyl, and trimethylsilyl) on frontier orbitals, charge distribution, static polarizabilities, molecular vibrations, bandgaps and photoluminescence quantum yields of 5,5′-diphenyl-2,2′-bithiophene (PTTP). By combining DFT calculations with cyclic voltammetry and absorption, photoluminescence, and Raman spectroscopies, we show that symmetric terminal substitution tunes the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energies of TPCOs within a range of ～0.7 eV, shifts the frequencies of the vibrational modes associated with the phenyl rings, changes the photoluminescence quantum yield by about two-fold and slightly changes the bandgap by ～0.1 eV. We demonstrate that these effects are governed by two factors: the Hammet constant of the substituents and their involvement in the π-conjugation/hyperconjugation described by the effective conjugation length of the substituted oligomer. A detailed picture underlying the effect of the terminal substituents on the electronic, vibrational and optical properties of TPCOs is presented. Overall, the unraveled relationships between the structure and the properties of the substituted PTTPs should facilitate a rational design of π-conjugated (co-)oligomers for efficient organic optoelectronic devices.

Metal-Free Aerobic Oxidative Selective C-C Bond Cleavage in Heteroaryl-Containing Primary and Secondary Alcohols

A transition-metal-free aerobic oxidative selective C-C bond-cleavage reaction in primary and secondary heteroaryl alcohols is reported. This reaction was highly efficient and tolerated various heteroaryl alcohols, generating a carboxylic acid derivative and a neutral heteroaromatic compound. Experimental studies combined with density functional theory calculations revealed the mechanism underlying the selective C-C bond cleavage. This strategy also provides an alternative simple approach to carboxylation reaction.

Modular synthesis of heptaarylindole

The first synthesis of heptaarylindole (HAI) has been accomplished using a coupling/ring transformation strategy. Four readily prepared modular units (diarylthiophenes, 2-arylaziridines, arylboronic acids, and arylalkynes) were joined together to provide

Wavelength Selective Generation of Aryl Radicals and Aryl Cations for Metal-Free Photoarylations

Photochemical reactions have become an important tool for organic chemists. Visible (solar) light can be conveniently adopted, however, only when using colored organic compounds or in photocatalyzed processes induced by visible light absorbing photocatalysts. Herein we demonstrate that a photolabile, colored moiety could be incorporated in a colorless organic compound with the aim of generating highly reactive intermediates upon exposure to visible (solar) light. Arylazo sulfones, colored thermally stable derivatives of aryl diazonium salts, were used as valuable substrates for the photoinduced metal-free synthesis of (hetero)biaryls with no need of a (photo)catalyst or of other additives to promote the reaction. Noteworthy, selective generation of aryl radicals and aryl cations can be attained at will by varying the irradiation conditions (visible light for the former and UVA light for the latter).

2-Aryl-indenylphosphine ligands: Design, synthesis and application in Pd-catalyzed Suzuki-Miyaura coupling reactions

A focused library of phosphine ligands was constructed for structural optimization. The catalyst can be used to perform the Suzuki-Miyaura cross-coupling reaction of aryl and heteroaryl chlorides.

Room-temperature palladium-catalysed Suzuki-Miyaura coupling of arylboric acid with aryl chlorides

An efficient room-temperature Pd-catalyzed Suzuki-Miyaura cross-coupling reaction of aryl-boronic acids with aryl chlorides is communicated here. The Pd(OAc)2/NiXantphos catalyst system enables the coupling reaction at room temperature in good

Direct 2-arylation of thiophene using low loading of a phosphine-free palladium catalyst

The direct coupling of aryl halides with thiophene would be a considerable advantage for sustainable development because of only HBr associated with a base as by-product is formed and the number of steps to prepare these compounds is less than in more cla

Air-stable Pd(R-allyl)LCl (L= Q-Phos, P(t-Bu)3, etc.) Systems for C-C/N Couplings: Insight into the Structure - Activity Relationship and Catalyst Activation Pathway

A series of Pd(R-allyl)LCl complexes [R = H, 1-Me, 1-Ph, 1-gem-Me 2, 2-Me; L = Q-Phos, P(t-Bu)3, P(t-Bu)2-(p- NMe2C6H4), P(t-Bu)2Np] have been synthesized and evaluated in the Buchwald - Hartwig aminations in detail, in addition to the preliminary studies on Suzuki coupling and α-arylation reactions. Pd(crotyl)Q-PhosCl (9) was found to be a superior catalyst to the other Q-Phos-based catalysts, and the reported in situ systems, in model coupling reactions involving 4-bromoanisole substrate with either N-methylaniline or 4-tertbutylbenzeneboronic acid. Precatalyst 9 also performed better (Figure presented) than the catalysts bearing P(t-Bu)2(p- NMe2C6H4) ligand; however, it is comparable to the new crotyl catalysts bearing P(t-Bu)3 or P(t-Bu)2Np ligands. In α-arylation of a biologically important model substrate, 1-tetralone, Pd(allyl)P(t-Bu)2(p-NMe2C6H 4)Cl (15) was found to be the best catalyst. The reason for the relatively higher activity of the crotyl complexes in comparison to the allyl derivatives in C-N bond formation reactions was investigated using X-ray crystallography in conjunction with NMR spectroscopic studies.

Novel Immunosuppressive Butenamides

2-thiophene 12 was carboxylated using butyllithium and carbon dioxide to give 5-thiophene-2-carboxylic acid 13.Conversion of the acid 13 using diphenyl phosphazidate and triethylamine gave 5-4-(1,