1625-91-8Relevant articles and documents
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Curtis,M.D.,Allred,A.L.
, p. 2554 - 2563 (1965)
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tert-Butylated spirobifluorene derivative incorporating triphenylamine groups: A deep-blue emitter with high thermal stability and good hole transport ability for organic light emitting diode applications
Xiao, Haibo,Ding, Lei,Ruan, Dong,Li, Benyan,Ding, Ning,Ma, Dongge
, p. 7 - 12 (2015)
Abstract A tert-butylated spirobifluorene derivative incorporating triphenylamine groups was synthesized starting from the readily available reagent biphenyl. Without any hole-transport layer, an unoptimized double-layer device exhibits excellent electroluminescent performances with a radiance of 3013 cd/m2 at 9.8 V, a maximum electroluminescent efficiency of 1.71 cd/A, a maximal external quantum efficiency of 2.58% at a brightness of 4.8 cd/m2, narrow full width at half-maximum (54 nm), and blue emission with Commission Internationale de l'Eclairage coordinates of (0.152, 0.103), which is close to the standard for blue. Compared to the reported organic light emitting diodes materials, the molecule displays very high thermal stability. In addition, the bilayer device showed a greatly improved performance as compared to a trilayer device with NPB as hole-transporting layer, which indicated that the molecule possesses good hole transport ability and can be good candidate for hole-transporting layer in organic light emitting diodes.
Shape-selective alkylation of biphenyl over H-[Al]-SSZ-24 zeolites with AFI topology
Ito, Akira,Maekawa, Hiroyoshi,Kawagoe, Hiroaki,Komura, Kenichi,Kubota, Yoshihiro,Sugi, Yoshihiro
, p. 215 - 223 (2007)
H-[Al]-SSZ-24 zeolites with AFI topology were synthesized through the alumination of [B]-SSZ-24 zeolites, and applied for the alkylation of biphenyl (BP). H-[Al]-SSZ-24 zeolites have high activity for the isopropylation. The shape-selective formation of 4,4′-diisopropylbiphenyl (4,40-DIPB) occurred at moderate temperature; however, the selectivity for 4,40-DIPB decreased with an increase in the reaction temperature. Isomerization of 4,4′-DIPB occurred at higher temperatures over internal and external acid sites when there are enough acid sites inside the channels. The channels can discriminate 4,4′-DIPB from the other DIPB isomers in their transition states; however, they can not prevent the isomerization of 4,4′-DIPB at higher temperatures. The selectivity for the least bulky 4,4′-dialkylbiphenyl increased with the bulkiness of alkylating agents in the order: isopropylation s-butylation t-butylation. These results strongly support the shape-selective formation of the least bulky products inside the channels of H-[Al]-SSZ-24 zeolites.
Nickel-Catalyzed Reductive Dicarbofunctionalization of Alkenes
García-Domínguez, Andrés,Li, Zhaodong,Nevado, Cristina
, p. 6835 - 6838 (2017)
An intermolecular, three-component reductive dicarbofunctionalization of alkenes is presented here. The combination of Ni catalysis with TDAE as final reductant enables the direct formation of Csp3-Csp3 and Csp3-Csp2 bonds across a variety of π-systems using two different electrophiles that are sequentially activated with exquisite selectivity under mild reaction conditions.
Homocoupling of arylboronic acids with a catalyst system consisting of a palladium(II) N-heterocyclic carbene complex and p-benzoquinone
Yamamoto, Yoshihiko
, p. 1913 - 1916 (2007)
In the presence of 1-3 mol% SIPr-ligated Pd(OAc)2 and 0.6 equivalent of p-benzoquinone, various arylboronic acids underwent homocoupling in MeOH at ambient temperature to produce symmetrical biaryls in 38-96% yields. Georg Thieme Verlag Stuttgart.
The alkylation of biphenyl over fourteen-membered ring zeolites. the influence of zeolite structure and alkylating agent on the selectivity for 4,4′-dialkylbiphenyl
Sugi, Yoshihiro,Maekawa, Hiroyoshi,Mulla, Shafeek Abdul Rashid,Ito, Akira,Naitoh, Chikayo,Nakagawa, Kazunori,Komura, Kenichi,Kubota, Yoshihiro,Kim, Jong-Ho,Seo, Gon
, p. 1418 - 1428 (2007)
Alkylation, i.e. isopropylation, s-butylation, and t-butylation, of biphenyl (BP) was examined over fourteen-mem-bered ring (14-MR) zeolites, CIT-5, UTD-1, and SSZ-53, in order to elucidate the relationships between structure of zeolites and bulkiness of alkylating agents on the shape-selective catalysis. CIT-5 zeolite (CFI) yielded 4,4′-diisopropyl- biphenyl (4,4′-DIPB) in the level of 50-60% in the isopropylation in the range of 150-300°C. 2,2′-, 2,3′-, and 2,4′-DIPB (2,x′-DIPB) isomers were obtained as the predominant DIPB isomers at lower temperatures, and the formation of 3,4′- and 3,3′-DIPB isomers increased with an increase in the temperature. However, the selectivities were in the level of 10- 15% for UTD-1 (DON) and SSZ-53 (SFH) zeolites in the range of 150-350°C. The s-butylation with 1-butene gave results similar to the isopropylation, although the selectivities for 4,4′-di-s-butylbiphenyl (4,4′-DSBB) were higher than those for 4,4′-DIPB at 250 °C: 80-85% for CFI, 40-50% for DON, and 30-40% for SFH. High selectivity for 4,4′-di-f-butylbiphenyl (4,4′-DTBB) was observed in the f-butylation at 250 °C: 95% for CFI, 90% for DON, and 80% for SFH. These differences are due to the spatial difference in their channels, and also due to bulkiness of alkylating agents, propene, 1-butene, and 2-methylpropene. The selectivity for 4,4′- dialkylbiphenyl (4,4′-DABP) was governed by the exclusion of the bulky DABP isomers at the transition state by steric restriction in the zeolite channels.
Nickel-catalyzed coupling of aryl bromides in the presence of alkyllithium reagents
Jhaveri, Sarav B.,Carter, Kenneth R.
, p. 6845 - 6848 (2008)
An easy approach towards the synthesis of compounds using coupling reactions of bromide compounds was demonstrated. A comparison of different alkyllithium reagents was made by examining the coupling of bromobenzene (1a). The molar ratio of bromobenzene to catalyst was 138:1 using [NiCl 2(dppp)] and bromobenzene, Bpy was added to the reaction solution as a ligand. Alkyllithium was added at half molar equivalents to that of phenyl bromide groups with the intention of generating an equimolar ratio of lithiated benzene anions to unreacted phenyl bromide groups. It was observed that decreasing the amount of [NiCl2(dppp)] from 25 to 12 mg, while maintaining the ratio to bpy, did not have a substantial effect on the yield of biphenyl formed. The one-pot synthetic technique demonstrate the use of alkyllithium reagents with a catalytic amount of nickel to syntheisze coupled aryl compounds.
Photochemische Untersuchungen an substituierten 2-Bis(diphenylstibino)methan>bis(phenyl)platin(II)-Verbindungen
Brune, Hans-Albert,Klotzbuecher, Rainer,Schmidtberg, Guenther
, p. 113 - 120 (1989)
The photochemical reactivity of the complexes 2-bis(diphenylstibino)methane>bis(phenyl)platinum(II) (4a-f) complexes having the substituents CH3, CH(CH3)2, C(CH3)3, Br, F, CF3 in the para-positions of the platinum-bonded phenyl rings has been
Synthesis of bisbicyclo[1.1.1]pentyldiazene. The smallest bridgehead diazene
Hossain,Timberlake
, p. 6282 - 6285 (2001)
Bisbicyclo[1.1.1]pentyldiazene, the smallest bicyclic azo compound, has been synthesized from the precursor [1.1.1]propellane via synthesis of N,N′-bis(bicyclo[1.1.1]pentyl)sulfamide and azoxybicyclo[1.1.1]pentane. The UV absorption of this diazene at 382 nm indicates that the compound is the trans isomer. Conversion to the cis isomer by irradiation was not possible because of attainment of a photostationary state. However, on the basis of the photochemical studies, the absorption of the cis-[1.1.1] isomer is estimated to be 384 nm.
Structural and catalytic properties of the [Ni(BIPHEP)X2] complexes, BIPHEP = 2,2-diphenylphosphino-1,1-biphenyl; X = Cl, Br
Ioannou, Polydoros-Chrysovalantis,Grigoropoulos, Alexios,Stergiou, Konstantina,Raptopoulou, Catherine P.,Psycharis, Vassilis,Svoboda, Jan,Kyritsis, Panayotis,Vohlídal, Ji?í
, (2021)
The synthesis and catalytic properties in Kumada C–C coupling of the [Ni(BIPHEP)X2] complexes, X = Cl (1), Br (2), are described. The crystal structures of the BIPHEP ligand and 2 are also presented and compared with previously reported crystal structures of atropisomeric bidentate phosphine ligands (P,P) and related [M(P,P)X2] complexes (M = Ni, Pd, Pt). BIPHEP crystallizes in the C2/c space group, with both enantiomers present in the unit cell. This is consistent with BIPHEP being a “tropos” ligand. Complex 2 crystallizes in the P21/a space group. There are two symmetry-independent molecules in the asymmetric unit, namely 2a and 2b, in which the BIPHEP ligand adopts the S or the R configuration, respectively. Complexes 2a and 2b exhibit a severely tetrahedrally-distorted square planar NiP2Br2 coordination sphere, with a PNiP bite angle of 93.3° and 94.7°, respectively. The observed catalytic behavior of complexes 1 and 2 in the Kumada coupling between p-tert-butyl-halogenobenzene and p-tolylmagnesium chloride is benchmarked against that of [Ni(dppp)Cl2], dppp = 1,3-bis(diphenylphoshpino)propane. However, all three complexes are catalytically inactive in the Suzuki-Miyaura coupling reaction.
Palladium-catalyzed intermolecular carbon-oxygen bond formation: A new synthesis of aryl ethers
Palucki,Wolfe,Buchwald
, p. 3395 - 3396 (1997)
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Synthesis and characterization of highly soluble and oxygen permeable new polyimides based on twisted biphenyl dianhydride and spirobifluorene diamine
Kim, Yun-Hi,Kim, Hyung-Sun,Kwon, Soon-Ki
, p. 7950 - 7956 (2005)
The novel spirobifluorene diamine monomer, 2,7-bis-amino-2′,7′- di-tert-butyl-9,9′-spirobifluorene, was obtained. The new organosoluble polyimides were prepared from spirobifluorene diamine containing bulky tert-butyl group and conventional dianhydrides as well as 2,2- ′bis(4″-tert-butylphenyl)4,4′,5,5′- biphenyltetracarboxylic dianhydride (BBBPAn) and 2,2′-bis(4″- trimethylsilylphenyl)-4,4′,5,5′biphenyltetracarboxylic dianhydride (BTSBPAn), which are composed of a noncoplanar twisted biphenyl unit containing bulky p-tert-butylphenyl groups and/or p-trimethylsilylphenyl groups by high-temperature one step polymerization. The structures of polymers were confirmed by various spectroscopic techniques. The weight-average molecular weights and polydispersities of resulting polymers were in the ranges 48 300-183 900 and 2.10-3.26, respectively. The bulky and twisted noncoplanar structural feature confers an enhanced solubility of the polyimides because of a decrease in the degree of molecular packing and crystallinity while imparting a significant increase in both Tg and thermal stability by restricting segmental mobility. The new polyimides exhibit the high oxygen permeabilities (P(O2) = 18-121 barrer) and O2/N2 gas separation properties (P(O2)/P(N2) = 2.2-9).
Exploration of Ionic Liquids as Soluble Supports for Organic Synthesis. Demonstration with a Suzuki Coupling Reaction
Miao, Weishi,Chan, Tak Hang
, p. 5003 - 5005 (2003)
(Equation Presented) The efficiency of ionic liquid supported synthesis was demonstrated by the Suzuki reaction of ionic liquid supported iodobenzoate compounds with arylboronic acids in aqueous media to give, after cleavage with ammonia/methanol, biaryl products in good yields and high purities, without the need for chromatographic purification.
Reductive Coupling of Aryl Halides via C—H Activation of Indene
Zhang, Bo-Sheng,Yang, Ying-Hui,Wang, Fan,Gou, Xue-Ya,Wang, Xi-Cun,Liang, Yong-Min,Li, Yuke,Quan, Zheng-Jun
, p. 1573 - 1579 (2021/05/28)
This paper describes the first case of a reductive coupling reaction with indene, a non-heteroatom olefin used as a reducing agent. The scope of the substrate is wide. The homo-coupling, cross-coupling, and synthesis of 12 and 14-membered rings were realized. The control experiment, indene-product curve and density functional theory calculations showed that the η3-palladium indene intermediate was formed by C—H activation in the presence of cesium carbonate. We speculate that the final product was obtained through a Pd (IV) intermediate or aryl ligand exchange. In addition, we excluded the formation of palladium anion (Pd(0)?) intermediates.
Pd-Catalyzed Cross-Coupling of Organostibines with Styrenes to Give Unsymmetric (E)-Stilbenes and (1 E,3 E)-1,4-Diarylbuta-1,3-dienes and Fluorescence Properties of the Products
Zhang, Zhao,Zhang, Dejiang,Zhu, Longzhi,Zeng, Dishu,Kambe, Nobuaki,Qiu, Renhua
supporting information, p. 5317 - 5322 (2021/06/28)
A general and effective palladium-catalyzed cross-coupling of organostibines with styrenes to give (E)-olefins was disclosed. By the use of an organostibine reagent, this method can produce unsymmetric (E)-1,2-diarylethylenes and (1E,3E)-1,4-diarylbuta-1,3-dienes in good yields with high E/Z selectivity and good functional group tolerance. Resveratrol and DMU-212 were synthesized in high yield. The protocol can be extended to the synthesis of (1E,3E,5E)-1,6-diphenylhexa-1,3,5-triene in 40% yield. Products 5e, 5f, and 7a showed good photoluminescence quantum yields ranging from 72 to 99%.
