Showing papers on "Substituent published in 2015"
TL;DR: Photochemical conditions, using Cu mediation, are used to produce the respective α-chloro-β-fluoroalkylcarbonyl products in excellent yields through an atom transfer radical addition (ATRA) process.
Abstract: Fluoroalkylsulfonyl chlorides, R(f)SO2Cl, in which R(f)=CF3, C4F9, CF2H, CH2F, and CH2CF3, are used as a source of fluorinated radicals to add fluoroalkyl groups to electron-deficient, unsaturated carbonyl compounds. Photochemical conditions, using Cu mediation, are used to produce the respective α-chloro-β-fluoroalkylcarbonyl products in excellent yields through an atom transfer radical addition (ATRA) process. Facile nucleophilic replacement of the α-chloro substituent is shown to lead to further diverse functionalization of the products.
331 citations
TL;DR: The presented data make an interesting case for organometallic chemistry that provides inherently better results when applied to substrates containing unprotected rather than protected -OH, -NHR, or -COOH groups.
Abstract: Reactions of internal alkynes with R3M-H (M = Si, Ge, Sn) follow an unconventional trans-addition mode in the presence of [Cp*Ru(MeCN)3]PF6 (1) as the catalyst; however, the regioselectivity is often poor with unsymmetrical substrates. This problem can be solved upon switching to a catalyst comprising a [Ru-Cl] bond, provided that the acetylene derivative carries a protic functional group. The R3M unit is then delivered with high selectivity to the alkyne-C atom proximal to this steering substituent. This directing effect originates from the ability of the polarized [Ru-Cl] bond to engage in hydrogen bonding with the protic substituent, which helps upload, activate, and lock the alkyne within the coordination sphere. An additional interligand contact of the chloride with the -MR3 center positions the incoming reagent in a matching orientation that translates into high regioselectivity. The proposed secondary interactions within the loaded catalyst are in line with a host of preparative and spectral data and with the structures of the novel ruthenium π-complexes 10 and 11 in the solid state. Moreover, the first X-ray structure of a [Ru(σ-stannane)] complex (12a) is presented, which indeed features peripheral Ru-Cl···MR3 contacts; this adduct also corroborates that alkyne trans-addition chemistry likely involves σ-complexes as reactive intermediates. Finally, it is discussed that interligand cooperativity might constitute a more general principle that extends to mechanistically distinct transformations. The presented data therefore make an interesting case for organometallic chemistry that provides inherently better results when applied to substrates containing unprotected rather than protected -OH, -NHR, or -COOH groups.
135 citations
TL;DR: A Rh(III) -catalyzed C-H activation/cyclative capture approach, involving a nucleophilic addition of C(sp(3) )-Rh species to polarized double bonds is reported, becoming the first intermolecular catalytic method to directly access 1-aminoindolines with a broad substituent scope under mild conditions.
Abstract: A Rh(III) -catalyzed C-H activation/cyclative capture approach, involving a nucleophilic addition of C(sp(3) )-Rh species to polarized double bonds is reported. This constitutes the first intermolecular catalytic method to directly access 1-aminoindolines with a broad substituent scope under mild conditions.
133 citations
TL;DR: In this article, the synthesis, characterization, and olefin (co)polymerization studies of a series of palladium complexes bearing phosphine phosphonic amide ligands were investigated.
Abstract: The synthesis, characterization, and olefin (co)polymerization studies of a series of palladium complexes bearing phosphine phosphonic amide ligands were investigated. In this ligand framework, substituents on three positions could be modulated independently, which distinguishes this class of ligand and provides a great deal of flexibilities and opportunities to tune the catalytic properties. The palladium complex with an o-MeO-Ph substituent on phosphine is one of the most active palladium catalysts in ethylene polymerization, with 1 order of magnitude higher activity than the corresponding classic phosphine-sulfonate palladium complex. Meanwhile, the polyethylene generated by this new palladium complex showed ca. 6 times higher molecular weight in comparison to that by the classic phosphine-sulfonate palladium complex. In ethylene/methyl acrylate copolymerization, the new palladium complex showed lower activity, generating copolymer with similar methyl acrylate incorporation and much higher molecular we...
116 citations
TL;DR: Preliminary results illustrate the potential of CAArC ligands in transition-metal catalysis.
Abstract: Cyclic (amino)(aryl)carbenes (CAArCs) result from the replacement of the alkyl substituent of cyclic (alkyl)(amino) carbenes (CAACs) by an aryl group. This structural modification leads to enhanced electrophilicity of the carbene center with retention of the high nucleophilicity of CAACs, and therefore CAArCs feature a small singlet-triplet gap. The isoindolium precursors are readily prepared in good yields, and deprotonation at low temperature, in the presence of [RhCl(cod)]2 and [(Me2S)AuCl] lead to air-stable rhodium and gold CAArC-supported complexes, respectively. The rhodium complexes promote the [3+2] cycloaddition of diphenylcyclopropenone with ethyl phenylpropiolate, and induce the addition of 2-vinylpyridine to alkenes by CH activation. The gold complexes allow for the catalytic three-component preparation of 1,2-dihydroquinolines from aniline and phenyl acetylene. These preliminary results illustrate the potential of CAArC ligands in transition-metal catalysis.
112 citations
TL;DR: In this article, six new non-symmetric dimers belonging to the family of compounds the (R,S)-(benzylidene-4-substituted-aniline)-2ʺ-methylbutyl-4ʹʹ-phenyloxy) benzoate-oxy) hexanoates have been prepared and their thermal behaviour characterised.
Abstract: Six new non-symmetric dimers belonging to the family of compounds the (R,S)-(benzylidene-4ʹ-substituted-aniline)-2ʺ-methylbutyl-4ʹʹʹ-(4ʹʹʹʹ-phenyloxy) benzoate-oxy) hexanoates have been prepared and their thermal behaviour characterised. The terminal substituents on the 4-benzylideneaniline fragment are H, CH3, C2H5, Cl, Br and I. All six dimers exhibit an enantiotropic nematic phase, and the efficiency of the terminal substituent in enhancing the nematic–isotropic transition temperature is largely consistent with that established for conventional low molar mass liquid crystals. This trend is discussed in terms of the size of the terminal substituent and its effect on the shape of the molecule. The halogen-substituted and ethyl-substituted dimers also exhibit smectic behaviour. For the halogen-substituted dimers, the driving force for smectic phase formation is considered to be, at least in part, the specific anisotropic interaction between the unlike mesogenic units. In contrast, for the ethyl-substitute...
102 citations
TL;DR: This transition-metal-free sequential synthesis process is compatible with aromatic, aliphatic, and cinnamic aldehydes, providing facile access to a variety of diazole derivatives bearing a 2-amino substituent in an efficient and scalable fashion.
Abstract: 2-Amino-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles were synthesized via condensation of semicarbazide/thiosemicarbazide and the corresponding aldehydes followed by I2-mediated oxidative C–O/C–S bond formation. This transition-metal-free sequential synthesis process is compatible with aromatic, aliphatic, and cinnamic aldehydes, providing facile access to a variety of diazole derivatives bearing a 2-amino substituent in an efficient and scalable fashion.
98 citations
TL;DR: In this article, a series of new pentiptycene-containing diamines with systematically varied substituent groups were designed and synthesized with high purity and high yields.
93 citations
TL;DR: A series of lithium, sodium, and potassium complexes with phenoxo-imine ligands M[(O-2-(RN═CH)C6H4] [R = C6H5; 2-tBuC 6H5, 2,6-iPr2C6 H3] and [O- 2-(RN)-CH)-4,6tBu2C 6 H4] 1−3(a-f) have been synthesized.
90 citations
TL;DR: The synthesis, structures, and magnetic properties of a family of air-stable star-shaped Co(II)Co(III)3 complexes were investigated and it was demonstrated that the anisotropy energy barrier can be finely tuned by the periphery substituent of the ligand and the countercation.
Abstract: The synthesis, structures, and magnetic properties of a family of air-stable star-shaped CoIICoIII3 complexes were investigated. These complexes contain only one paramagnetic Co(II) ion with the approximate D3 coordination environment in the center and three diamagnetic Co(III) ions in the peripheral. Magnetic studies show their slow magnetic relaxation in the absence of an applied dc field, which is characteristic behavior of single-molecule magnets (SMMs), caused by the individual Co(II) ion with approximate D3 symmetry in the center. Most importantly, it was demonstrated that the anisotropy energy barrier can be finely tuned by the periphery substituent of the ligand and the countercation. The anisotropy energy barrier can be increased significantly from 38 K to 147 K.
87 citations
TL;DR: This Ni-catalyzed alkynylation procedure provides an alternative approach to construct a C(sp(2)-C(sp) bond and showed good tolerance toward not only a wide range of (hetero)aryl amides but also the rarely studied α,β-unsaturated alkenyl amide.
Abstract: An efficient nickel catalyst system for the direct ortho C–H alkynylation of the amides has been successfully developed with the directing assistance of 8-aminoquinoline. It was found that the flexible bis(2-dimethylaminoethyl) ether (BDMAE) ligand was critical to achieve the optimized reactivity. This protocol showed good tolerance toward not only a wide range of (hetero)aryl amides but also the rarely studied α,β-unsaturated alkenyl amide. The directing amide group could be easily transformed to aldehyde or ester in high yields. Meanwhile, the removable TIPS substituent on the resultant aryl/alkenyl alkynes could be further converted to an aryl moiety through a Sila–Sonogashira coupling reaction. This Ni-catalyzed alkynylation procedure provides an alternative approach to construct a C(sp2)–C(sp) bond.
TL;DR: Mechanistic studies elucidated the sequence of hydrosilylation in this multiple reduction cascade: 1,2- or 1,4-hydrosilylated as an initial step depending on the substituent position, followed by selective hydrosallylation of enamine double bonds eventually affording β-silylated azacyclic compounds.
Abstract: Tris(pentafluorophenyl)borane-catalyzed silylative reduction of pyridines has been developed giving rise to the formation of sp(3) C-Si bonds selectively beta to the nitrogen atom of azacyclic products. Depending on the position and nature of pyridine substituents, structurally diverse azacycles are obtained with high selectivity under the borane catalysis. Mechanistic studies elucidated the sequence of hydrosilylation in this multiple reduction cascade: 1,2- or 1,4-hydrosilylation as an initial step depending on the substituent position, followed by selective hydrosilylation of enamine double bonds eventually affording β-silylated azacyclic compounds.
TL;DR: A comparative analysis of the chemical shift data revealed the substituent effect of acetyl groups at the 2-, 3-, and 6-positions on the (1)H and (13)C nuclei in the same AGU.
TL;DR: DFT calculations show that (amino)(carboxy) radicals evolve from C-centered radical to ambidentate C,O-radicals when increasing the electron-withdrawing properties of the carbonyl substituent.
Abstract: A series of monomeric (amino)(carboxy) radicals featuring carbonyl substituents with increasing electron-withdrawing properties (3a, phenyl; 3b, 3,5-bis(trifluoromethyl)phenyl; 3c, perfluorophenyl; 3d, heptafluoropropyl; 3e, 2H-pyrroliumyl) were synthesized in two or three steps from stable cyclic (alky)(amino)carbenes (CAACs). Although (amino)(carboxy) radicals had been previously considered as highly air-sensitive, some of these compounds feature half-lives of hours (3d), and even days (3c and 3e) in well-aerated solutions. DFT calculations show that (amino)(carboxy) radicals evolve from C-centered radical to ambidentate C,O-radicals when increasing the electron-withdrawing properties of the carbonyl substituent. This is paralleled with a destabilization of the peroxide resulting from the addition of dioxygen to the radical. This latter reaction is even predicted to be endothermic for substituents with Hammett constant σp > 0.2.
TL;DR: In this paper, the synthesis of well-defined poly(3,3,�-didodecyl-2,2′:5,4,2,5,2.5,1.2, 5, 2.5)-quaterthiophene (PQT12) from a direct heteroarylation polymerization (DHAP) was reported.
Abstract: We report the synthesis of well-defined poly(3,3‴-didodecyl-2,2′:5′,2″:5″,2‴-quaterthiophene) (PQT12) from a direct heteroarylation polymerization (DHAP) of 5-bromo-3,3‴-didodecyl-2,2′:5′,2″:5″,2‴-quaterthiophene (monomer A) and 5-bromo-3′,4″-didodecyl-2,2′:5′,2″:5″,2‴-quaterthiophene (monomer B). Experiments with different catalysts, ligands, additives, and solvents have revealed that the utilization of Herrmann–Beller catalyst and P(o-NMe2Ph)3 can lead to selective thiophene–thiophene couplings. In this regard, solid-state optical and thermal measurements were particularly useful to detect the presence of β-branching and indicate that minor molecular defects can induce important changes within the supramolecular organization. We also highlight the fact that steric protection around unsubstituted β-positions of α-bromothiophene units is needed to obtain a good selectivity of the cross-couplings at the α-positions. This can be achieved by the presence of a substituent at an adjacent β-position or the util...
TL;DR: In this article, the substituent effect of epoxides on CO2/epoxide copolymerization catalyzed by a nanosized zinc-cobalt-III double metal cyanide complex [Zn-Co(III) DMCC] was described.
Abstract: In this study, we describe the substituent effect of epoxides on CO2/epoxide copolymerization catalyzed by a nanosized zinc–cobalt(III) double metal cyanide complex [Zn–Co(III) DMCC]. The Zn–Co(III) DMCC catalyzed the copolymerization of CO2 with 11 epoxides with alkyl or aryl groups at 50–60 °C within 15 h. The reaction afforded various CO2/epoxide copolymers with high epoxide conversion efficiencies up to 100%. The alternating degree (FCO2) of the resulting copolymer was solely decided by the steric hindrance of the substituents of the epoxides regardless of their electron-donating or withdrawing properties. Substituents with large steric hindrances (2, 2-dimethyl, tert-butyl, cyclohexyl, decyl, and benzyl) led to highly alternating degrees (up to 100%). The regioselective CO2/epoxide copolymerization was dominated by the electron induction effect of the substituent. The electron-withdrawing substituent such as phenyl and benzyl induced regioselective ring-opening at the methine site of the epoxide. For...
TL;DR: Structural-activity relationship (SAR) studies suggest that oxadiazole benzohydrazones (6-28) inhibitory potential is dependent on substitution of the N-benzylidene part, and reveals the important presence of hydroxyl and halo groups to have enzyme inhibitory activity.
TL;DR: Along with the high phosphorescence efficiency, the bulkiness of the 2-R-o-carborane unit is shown to play an important role in improving device performance and display higher performance than the device based on the parent [(ppy)2 Ir(acac)] complex.
Abstract: A series of [(C^N)2 Ir(acac)] complexes [{5-(2-R-CB)ppy}2 Ir(acac)] (3 a-3 g; acac=acetylacetonate, CB=o-carboran-1-yl, ppy=2-phenylpyridine; R=H (3 a), Me (3 b), iPr (3 c), iBu (3 d), Ph (3 e), CF3 C6 H4 (3 f), C6 F5 (3 g)) with various 2-R-substituted o-carboranes at the 5-position in the phenyl ring of the ppy ligand were prepared. X-ray diffraction studies revealed that the carboranyl CC bond length increases with increasing steric and electron-withdrawing effects from the 2-R substituents. Although the absorption and emission wavelengths of the complexes are almost invariant to the change of 2-R group, the phosphorescence quantum efficiency varies from highly emissive (ΦPL ≈0.80 for R=H, alkyl) to poorly emissive (R=aryl) depending on the 2-R group and the polarity of the medium. Theoretical studies suggest that 1) the almost nonemissive nature of the 2-aryl-substituted complexes is mainly attributable to the large contribution to the LUMO in the S1 excited state from an o-carborane unit and 2) the variation in the CC bond length between the S0 and T1 state structures increases with increasing steric (2-alkyl) and electronic effects (2-aryl) of the 2-R substituent and the polarity of the solvent. The solution-processed electroluminescence (EL) devices that incorporated 3 b and 3 d as emitters displayed higher performance than the device based on the parent [(ppy)2 Ir(acac)] complex. Along with the high phosphorescence efficiency, the bulkiness of the 2-R-o-carborane unit is shown to play an important role in improving device performance.
TL;DR: Organocatalytic ring opening polymerization of eight-membered cyclic carbonates was explored as a route to access narrowly dispersed polymers of predictable molecular weights and found to be N-substituent dependent.
Abstract: Aliphatic N-substituted functional eight-membered cyclic carbonates were synthesized from N-substituted diethanolamines by intramolecular cyclization. On the basis of the N-substituent, three major subclasses of carbonate monomers were synthesized (N-aryl, N-alkyl and N-carbamate). Organocatalytic ring opening polymerization (ROP) of eight-membered cyclic carbonates was explored as a route to access narrowly dispersed polymers of predictable molecular weights. Polymerization kinetics was highly dependent on the substituent on the nitrogen atom and the catalyst used for the reaction. The use of triazabicyclodecene (TBD), instead of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), as the catalyst for the N-alkyl substituted monomers significantly enhanced the rate of polymerizations. Computational studies were performed to rationalize the observed trends for TBD catalyzed polymerizations. With the optimal organocatalyst all monomers could be polymerized generating well-defined polymers within a timespan of ≤2 h wi...
TL;DR: The substitution of a methyl to an octyl group in the ancillary triazolylidene ligand has been shown to increase the activity of the corresponding iridium complex in water oxidation catalysis when using cerium(IV) as sacrificial oxidant as discussed by the authors.
Abstract: The substitution of a methyl to an octyl group in the ancillary triazolylidene ligand—an apparently simple variation—induces a more than 10-fold increase of activity of the corresponding iridium complex in water oxidation catalysis when using cerium(IV) as sacrificial oxidant. Detailed NMR studies suggest that various different molecular species form, all bearing the intact triazolylidene ligand. The octyl substituent is essential for inducing the association of the iridium species, thus generating extraordinarily active multimetallic catalytic sites. Their accessibility and steady-state concentration is critically dependent on the type of sacrificial oxidant and specifically on the cerium ammonium nitrate versus catayst ratio.
TL;DR: Unprecedented coordination-insertion polymerizations of polar methoxyl substituted styrene derivatives, in despite of the position of the substituent, have been achieved using a pyridyl methylene fluorenyl yttrium bis(alkyl) precursor with high activity to give polar polystyrenes of high molecular weight and perfect syndiotacticity.
TL;DR: In this paper, a systematic quantum chemical study was performed to investigate the effects of carbene substituent, porphyrin substitution, and axial ligand on IPC formation pathways.
Abstract: Iron porphyrin carbenes (IPCs) are important intermediates in various chemical reactions catalyzed by iron porphyrins and engineered heme proteins, as well as in the metabolism of various xenobiotics by cytochrome P450. However, there are no prior theoretical reports to help understand their formation mechanisms and identify key information governing the binding mode, formation feasibility, and stability/reactivity. A systematic quantum chemical study was performed to investigate the effects of carbene substituent, porphyrin substituent, and axial ligand on IPC formation pathways. Results not only are consistent with available experimental data but also provide a number of unprecedented insights into electronic, steric, and H-bonding effects of various structural factors on IPC formation mechanisms. These results shall facilitate research on IPC and related systems for sustainable chemical catalysis and biocatalysis.
TL;DR: The syntheses of unsymmetrical N-heterocyclic carbenes (NHCs) that contain a single N-bound icosahedral carborane anion substituent are reported.
TL;DR: In this article, a series of C4v-symmetric Cr(CNR)(CO)5 complexes featuring various alkyl, aryl, and m-terphenyl substituents have been prepared.
Abstract: To assess the relative electronic influence of highly substituted aryl isocyanides on transition metal centers, a series of C4v-symmetric Cr(CNR)(CO)5 complexes featuring various alkyl, aryl, and m-terphenyl substituents have been prepared. A correlation between carbonyl-ligand 13C{1H} NMR chemical shift (δCO) and calculated Cotton–Kraihanzel (C–K) force constant (kCO) is presented for these complexes to determine the relative changes in isocyanide σ-donor/π-acid ratio as a function of substituent identity and pattern. For nonfluorinated aryl isocyanides possessing alkyl or aryl substitution, minimal variation in effective σ-donor/π-acid ratio is observed over the series. In addition, aryl isocyanides featuring strongly electron-releasing substituents display an electronic influence that nearly matches that of nonfluorinated alkyl isocyanides. Lower σ-donor/π-acid ratios are displayed by polyfluorinated aryl isocyanide ligands. However, the degree of this attenuation relative to nonfluorinated aryl isocya...
TL;DR: The dual-emissive properties of solid-state difluoroboron β-diketonate-poly(lactic acid) (BF2bdkPLA) materials have been utilized for biological oxygen sensing and can be utilized as ultrasensitive oxygen sensors.
Abstract: The dual-emissive properties of solid-state difluoroboron β-diketonate-poly(lactic acid) (BF2bdkPLA) materials have been utilized for biological oxygen sensing. In this work, BF2dbm(X)PLA materials were synthesized, where X = H, F, Cl, Br, and I. The effects of changing the halide substituent and PLA polymer chain length on the optical properties in dilute CH2Cl2 solutions and solid-state polymer films were studied. These luminescent materials show fluorescence, phosphorescence, and lifetime tunability on the basis of molecular weight, as well as lifetime modulation via the halide substituent. Short BF2dbm(Br)PLA (6.0 kDa) and both short and long BF2dbm(I)PLA polymers (6.0 or 20.3 kDa) have fluorescence and intense phosphorescence ideal for ratiometric oxygen sensing. The lighter halide-dye polymers with hydrogen, fluorine, and chlorine substitution have longer phosphorescence lifetimes and can be utilized as ultrasensitive oxygen sensors. Photostability was also analyzed for the polymer films.
TL;DR: Density functional methods are used to examine the geometries and energetics of molecules containing a phenyl ring joined to the trigonal bipyramidal SF3 framework and a strengthening arises when an electron-withdrawing substituent is placed ortho to the ether and meta to SF3, while electron-releasing species produce an opposite effect.
Abstract: Density functional methods are used to examine the geometries and energetics of molecules containing a phenyl ring joined to the trigonal bipyramidal SF3 framework. The phenyl ring has a strong preference for an equatorial position. This preference remains when one or two ether -CH2OCH3 groups are added to the phenyl ring, ortho to SF3, wherein an apical structure lies nearly 30 kcal/mol higher in energy. Whether equatorial or apical, the molecule is stabilized by a S···O chalcogen bond, sometimes augmented by CH···F or CH···O H-bonds. The strength of the intramolecular S···O bond is estimated to lie in the range between 3 and 6 kcal/mol. A secondary effect of the S···O chalcogen bond is elongation of the S-F bonds. Solvation of the molecule strengthens the S···O interaction. Addition of substituents to the phenyl ring has only modest effects upon the S···O bond strength. A strengthening arises when an electron-withdrawing substituent is placed ortho to the ether and meta to SF3, while electron-releasing species produce an opposite effect.
TL;DR: In this paper, the synthesis and properties of transition metal complexes containing the heavier Group 15 Sb/Bi ligands, of general formula ER3 (E = Sb or Bi; R = alkyl, aryl etc, and may include a pendant donor group such as amine or ether) and ER(3-n)Xn (E= Sb and Bi; X = 0-3) are reviewed.
TL;DR: It is shown that an ortho boronic acid substituent makes aryl ketones rapidly conjugate with α-nucleophiles at neutral pH, comparable to the fastest bioorthogonal conjugations known to date.
Abstract: Bioorthogonal reactions that are fast and reversible under physiological conditions are in high demand for biological applications. Herein, it is shown that an ortho boronic acid substituent makes aryl ketones rapidly conjugate with α-nucleophiles at neutral pH. Specifically, 2-acetylphenylboronic acid and derivatives were found to conjugate with phenylhydrazine with rate constants of 10(2) to 10(3) M(-1) s(-1) , comparable to the fastest bioorthogonal conjugations known to date. (11) B NMR analysis revealed the varied extent of iminoboronate formation of the conjugates, in which the imine nitrogen forms a dative bond with boron. The iminoboronate formation activates the imines for hydrolysis and exchange, rendering these oxime/hydrazone conjugations reversible and dynamic under physiological conditions. The fast and dynamic nature of the iminoboronate chemistry should find wide applications in biology.
TL;DR: Three-component reaction between RCF2CH2NH2·HCl, NaNO2 and electron-deficient alkynes significantly depends on substituent "R", giving the fluorinated pyrazoles in high yields when "R" is a fluorine atom or a fluoroalkyl group.
Abstract: Three-component reaction between RCF2CH2NH2·HCl, NaNO2 and electron-deficient alkynes significantly depends on substituent “R”. The reaction gives the fluorinated pyrazoles in high yields when “R” is a fluorine atom or a fluoroalkyl group. With other “R” unexpected products are formed.
Patent•
26 Feb 2015
TL;DR: An organic thin film transistor containing a compound represented by the formula (1) in a semiconductor active layer has a high carrier mobility and a small fluctuation of the threshold voltage after repeated driving.
Abstract: An organic thin film transistor containing a compound represented by the formula (1) in a semiconductor active layer has a high carrier mobility and a small fluctuation of the threshold voltage after repeated driving. R 1 to R 12 represent a hydrogen atom or a substituent, provided that at least one of R 1 to R 12 represents a substituent represented by the formula (W), or all of R 1 to R 12 represent a hydrogen atom. * represents a position bonded to the naphthobisbenzofuran skeleton. L represents a single bond, a divalent linking group, an oligoethyleneoxy group having a repeating number of an ethyleneoxy unit of 2 or more, or an oligosiloxane group having 2 or more silicon atoms.