204191-68-4Relevant academic research and scientific papers
Building blocks for n-type organic electronics: Regiochemically modulated inversion of majority carrier sign in perfluoroarene-modified polythiophene semiconductors
Facchetti, Antonio,Yoon, Myung-Han,Stern, Charlotte L.,Katz, Howard E.,Marks, Tobin J.
, p. 3900 - 3903 (2003)
A new family of perfluoroarene-modified thiophene semiconductors 1-3 has been synthesized to assess the influence of perfluoroarene introduction and regiochemistry on molecular and thin-film transistor properties. Compound 1 is an n-type semiconductor wit
Perfluorophenylation of aromatic and heteroaromatic compounds with pentafluorobenzenesulfonyl chloride catalyzed by a ruthenium (ii) phosphine complex
Kamigata, Nobumasa,Yoshikawa, Manabu,Shimizu, Toshio
, p. 91 - 95 (1998)
The reactions of pentafluorobenzenesulfonyl chloride with benzene and thiophene derivatives in the presence of a ruthenium(II) catalyst proceeded at 240°C, with extrusion of sulfur dioxide and hydrogen chloride, to give the corresponding perfluorophenylated compounds.
Syntheses of 2-(pentafluorophenyl)thiophene derivatives via the palladium-catalyzed Suzuki reaction
Takimiya, Kazuo,Niihara, Naoto,Otsubo, Tetsuo
, p. 1589 - 1592 (2005)
Various bis(pentafluorophenyl)-substituted thiophene and selenophene derivatives are effectively synthesized by the palladium-catalyzed Suzuki reaction using pentafluorophenyl boronic acid. Georg Thieme Verlag Stuttgart.
Anion Recognition by Neutral Chalcogen Bonding Receptors: Experimental and Theoretical Investigations
Navarro-García, Encarnación,Galmés, Bartomeu,Velasco, María D.,Frontera, Antonio,Caballero, Antonio
supporting information, p. 4706 - 4713 (2020/02/27)
The utilization of neutral receptors for the molecular recognition of anions based on chalcogen bonding (ChB) is an undeveloped area of host-guest chemistry. In this manuscript, the synthesis of two new families of sulfur, selenium, and tellurium-based ChB binding motifs are reported. The stability of the thiophene, selenophene, and tellurophene binding motifs has enabled the determination of the association constants for ChB halide anion binding in the polar aprotic solvent THF by 1H, 77Se, and 125Te NMR experiments. Two different aromatic cores are used and one or two Ch-binding motifs are incorporated with the purpose of encapsulating the anion, offering up to two concurrent chalcogen bonds. Theoretical calculations and NMR experiments reveal that, for S and Se receptors, hydrogen-bonding interactions involving the acidic H atom adjacent to the chalcogen atom are energetically favored over the ChB interaction. However, for the tellurophene binding motif, the σ-hole interaction is competitive and more favored than the hydrogen bond.
End-Capping Groups for Small-Molecule Organic Semiconducting Materials: Synthetic Investigation and Photovoltaic Applications through Direct C–H (Hetero)arylation
Lu, Te-Jui,Lin, Po-Han,Lee, Kun-Mu,Liu, Ching-Yuan
, p. 111 - 123 (2017/01/14)
A Pd-catalyzed C–H (hetero)arylation methodology has been optimized for the efficient synthesis of various useful end-capping groups that are widely applied in small-molecule optoelectronic materials. We report herein the synthesis of a broad scope of target molecules ranging from donor-type through acceptor-type to hybrid-type end-capping groups. To demonstrate their application in dye-sensitized solar cells, we have designed two new D–A–π–A′-type organic sensitizers (CYL-3 and CYL-4), which were synthesized in a step-economic manner by sequential C–H arylations using the facilely obtained end-capping groups. The devices based on CYL-3 and CYL-4 give Vocvalues of 0.67–0.71 V, Jscvalues of 10.07–11.63 mA cm–2, and FF values of 70.6–72.9 %, which correspond to overall power conversion efficiencies of 4.76–6.02 %. This work is expected to become a practical synthetic alternative allowing materials scientists to access small-molecule organic materials in fewer synthetic transformations.
NOVEL PRECATALYST SCAFFOLDS FOR CROSS-COUPLING REACTIONS, AND METHODS OF MAKING AND USING SAME
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Page/Page column 55; 57, (2016/05/02)
The present invention provides novel transition-metal precatalysts that are useful in preparing active coupling catalysts. In certain embodiments, the precatalysts of the invention are air-stable and moisture-stable. The present invention further provides methods of making and using the precatalysts of the invention.
Design of a versatile and improved precatalyst scaffold for palladium-catalyzed cross-coupling: (η3-1-tBu-indenyl)2(μ-Cl)2Pd2
Melvin, Patrick R.,Nova, Ainara,Balcells, David,Dai, Wei,Hazari, Nilay,Hruszkewycz, Damian P.,Shah, Hemali P.,Tudge, Matthew T.
, p. 3680 - 3688 (2015/06/16)
We describe the development of (η3-1-tBu-indenyl)2(μ-Cl)2Pd2, a versatile precatalyst scaffold for Pd-catalyzed cross-coupling. Our new system is more active than commercially available (η3-cinnamyl)2(μ-Cl)2Pd2 and is compatible with a range of NHC and phosphine ligands. Precatalysts of the type (η3-1-tBu-indenyl)Pd(Cl)(L) can either be isolated through the reaction of (η3-1-tBu-indenyl)2(μ-Cl)2Pd2 with the appropriate ligand or generated in situ, which offers advantages for ligand screening. We show that the (η3-1-tBu-indenyl)2(μ-Cl)2Pd2 scaffold generates highly active systems for a number of challenging cross-coupling reactions. The reason for the improved catalytic activity of systems generated from the (η3-1-tBu-indenyl)2(μ-Cl)2Pd2 scaffold compared to (η3-cinnamyl)2(μ-Cl)2Pd2 is that inactive PdI dimers are not formed during catalysis.
Nickel-catalyzed decarboxylative cross-coupling of perfluorobenzoates with aryl halides and sulfonates
Sardzinski, Logan W.,Wertjes, William C.,Schnaith, Abigail M.,Kalyani, Dipannita
supporting information, p. 1256 - 1259 (2015/05/20)
A Ni-catalyzed method for the coupling of perfluorobenzoates with aryl halides and pseudohalides is described. Aryl iodides, bromides, chlorides, triflates, and tosylates participate in these transformations to afford the products in good yields. Penta-, tetra-, and trifluorinated biaryl compounds are obtained using these newly developed Ni-catalyzed decarboxylative cross-coupling reactions.
Palladium-catalyzed coupling reaction of perfluoroarenes with diarylzinc compounds
Ohashi, Masato,Doi, Ryohei,Ogoshi, Sensuke
supporting information, p. 2040 - 2048 (2014/03/21)
This report describes the first Pd0-catalyzed cross-coupling of hexafluorobenzene (C6F6) with diarylzinc compounds to give a variety of pentafluorophenyl arenes. This reaction could be applied to other perfluoroarenes, such as octafluorotoluene, pentafluoropyridine, and perfluoronaphthalene, to give the corresponding polyfluorinated coupling products. The optimal ligand in this catalytic reaction was PCy3, and lithium iodide was indispensable as an additive for the coupling reaction. One of the roles of lithium iodide in this catalytic reaction was to promote the oxidative addition of one Ci￡F bond of C6F 6 to palladium. Stoichiometric reactions revealed that an expected oxidative-addition product, trans-[Pd(C6F5)I(PCy 3)2], generated from the reaction of [Pd(PCy 3)2] with C6F6 in the presence of lithium iodide, was not involved in the catalytic cycle. Instead, a transient three-coordinate, monophosphine-ligated species, [Pd(C6F 5)I(PCy3)], emerged as a potential intermediate in the catalytic cycle. Therefore, we isolated a novel PdII complex, [Pd(C6F5)I(PCy3)(py)], in which pyridine (py) acted as a labile ligand to generate the transient species. In fact, in the presence of lithium iodide, this PdII complex was found to react smoothly with diphenylzinc to give the desired pentafluorophenyl benzene, whereas the same reaction conducted in the absence of lithium iodide resulted in a decreased yield of pentafluorophenyl benzene, which indicated that the other role of lithium iodide was to enhance the reactivity of the organozinc species during the transmetalation step.
N-substituted 2-aminobiphenylpalladium methanesulfonate precatalysts and their use in C-C and C-N cross-couplings
Bruno, Nicholas C.,Niljianskul, Nootaree,Buchwald, Stephen L.
, p. 4161 - 4166 (2014/05/20)
A series of phosphine-ligated palladium precatalysts based on N-methyl- and N-phenyl-2-aminobiphenyl have been developed. Substitution at the nitrogen center prevents the presence of traces of aminobiphenyls that contain a free -NH2 group from contaminating cross-coupling products. These precatalysts produce N-substituted carbazoles upon activation, which cannot consume starting materials. These precatalysts were efficiently generated from 2-aminobiphenyl with minimal purification and found to be highly effective in Suzuki-Miyaura and C-N cross-coupling reactions.
