- Oxidation-state-dependent photochemistry of sulfur-bridged anthracenes
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What's up sulfur? The photochemical reactivity, including a mechanistic study of sulfur-bridged anthracenes is reported. The oxidation state of the bridging sulfur (SOn) dictates the excited-state behavior of these molecules (see picture). Copyright
- Christensen, Peter R.,Patrick, Brian O.,Caron, Elise,Wolf, Michael O.
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- Reversible mechanochromic luminescence of phenothiazine-based 10,10′-bianthracene derivatives with different lengths of alkyl chains
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A series of 10,10′-bis(2-(N-alkylphenothiazine-3-yl)vinyl)-9,9′-bianthracene compounds (PVBAn, n = 2, 8, 12 and 16) with different lengths of N-alkyl chains have been designed and synthesized to systematically investigate the effect of chain length on their solid-state fluorescence properties. The results showed that these compounds emitted strong fluorescence in solution and in the solid state. Their emission wavelengths were also strongly affected by solvent polarity, indicating intramolecular charge transfer (ICT) transitions. Interestingly, the fluorescence emission and grinding-induced spectral shifts of PVBAn solids are alkyl length-dependent. PVBA2 shows the smallest fluorescence and absorption spectrum shifts under mechanical force stimuli. Homologues with longer alkyl chains exhibit similar mechanochromic behaviors and larger fluorescence contrasts after grinding. Moreover, the fluorescence emission of ground solid PVBA16 can recover at room temperature, but other compounds need high temperatures for fluorescence to be restored. Differential scanning calorimetry experiments reveal that the cold-crystallization temperature difference is responsible for thermal restoration behaviors. This work demonstrates the feasibility of tuning the solid-state optical properties of fluorescent organic compounds by combining the simple alteration of chemical structure and the physical change of aggregate morphology under external stimuli.
- Xue, Pengchong,Yao, Boqi,Liu, Xuhui,Sun, Jiabao,Gong, Peng,Zhang, Zhenqi,Qian, Chong,Zhang, Yuan,Lu, Ran
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- Fine tuning of bipolar side group on dual anthracene core derivatives for highly efficient blue emitters
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Three bipolar blue fluorescent materials were newly synthesized by attaching diphenylamine (DPA), triphenylamine (TPA), and 9-phenylcarbazole amine (PCA) as an electron donating group and 2,4- diphenyl-1,3,5-triazine (DPT) as an electron withdrawing group to the dual anthracene core moiety. Compounds are [10'-(4,6-Diphenyl-[1,3,5]triazin-2-yl)-[9,9']bianthracenyl-10-yl]-diphenyl-amine (DPA-AA-DPT), {4-[10'-(4,6-Diphenyl-[1,3,5]triazin-2-yl)-[9,9']bianthracenyl-10-yl]-phenyl}-diphenyl- amine (TPA-AA-DPT), and 9-(4-(10'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[9,9′-bianthracen]-10-yl)phenyl)- 9H-carbazole (PCA-AA-DPT), respectively. The optical, thermal, and electroluminescence (EL) properties of the synthesized materials were measured. Newly bipolar materials were found to have blue emission in the solution state and to acquire high PLQY values. A device doped with PCA-AA- DPT showed a very high efficiency of 6.86 cd/A and EQE of 5.53% at a high current density without roll-off phenomenon.
- Kang, Seokwoo,Lee, Hayoon,Park, Jongwook,Park, Sunwoo,Shim, Yeonhee
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- EXPERIMENTAL STUDY OF DIMERIZATION OF RADICAL ANIONS OF AROMATIC CARBONYL COMPOUNDS
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The rate constants of dimerization (k1) of radical anions of acetophenone, 1-acetylnaphthalene, 9-acetylanthracene, 9-formylanthracene, and anthracene in DMF containing 0.02 M tetrabutyloammonium bromide were determined by differential cyclic voltammetry.It was shown that the values of k1 of the radical anions investigated are correlated with the values of the boundary electron density on the reaction sites, which in turn increase symbatically with an increase in the size of the aryl fragment or on incorporation of electron-acceptor functional groups in the anthracene nucleus.
- Mendkovich, A. S.,Churilina, A. P.,Rusakov, A. I.,Gul'tyai, V. P.
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- A laser desorption ionization mass spectrometry investigation of triarylboranes and tri-9-anthrylborane photolysis products
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Laser desorption ionization (LDI) mass spectra have been obtained for the photolysis products of tri-9-anthrylborane (TAB) in the solvents toluene, cyclohexene, and tetrahydrofuran; and for the solid triarylboranes: TAB, trimesitylborane (TMB), and tri-(2,6-dimethylphenyl)borane (TXyB). The major single solution photolysis product of TAB is 9,9′-dianthryl. Other products are rationalized in terms of an anthrylborylene intermediate (AnthB:). LDI mass spectrometry of the triarylboranes yields molecular ions in good abundance, providing a simple and selective method of characterization. Fragmentation patterns in some cases are interpreted in terms of photochemical reactions prior to ionization.
- Ramsey, Brian G.,Bier, Mark E.
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- Photochemical reaction of anthracene in cyclohexane polycrystals dispersed in liquid nitrogen
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U.v. photolysis of a polycrystalline solution of anthracene in cyclohexane at 77 K followed by separation of the stable photoproducts at room temperature, yielded 9,10-dihydroanthracene, 9-cyclohexyl-9,10-dihydroanthracene, 9-cyclohexylanthracene, and oxidized derivatives of anthracene.
- Lamotte, Michel,Lapouyade, Rene,Pereyre, Josette,Joussot-Dubien, Jacques
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- Diphenylanthracene Dimers for Triplet-Triplet Annihilation Photon Upconversion: Mechanistic Insights for Intramolecular Pathways and the Importance of Molecular Geometry
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Novel approaches to modify the spectral output of the sun have seen a surge in interest recently, with triplet-triplet annihilation driven photon upconversion (TTA-UC) gaining widespread recognition due to its ability to function under low-intensity, noncoherent light. Herein, four diphenylanthracene (DPA) dimers are investigated to explore how the structure of these dimers affects upconversion efficiency. Also, the mechanism responsible for intramolecular upconversion is elucidated. In particular, two models are compared using steady-state and time-resolved simulations of the TTA-UC emission intensities and kinetics. All dimers perform TTA-UC efficiently in the presence of the sensitizer platinum octaethylporphyrin. The meta-coupled dimer 1,3-DPA2 performs best yielding a 21.2% upconversion quantum yield (out of a 50% maximum), which is close to that of the reference monomer DPA (24.0%). Its superior performance compared to the other dimers is primarily ascribed to the longer triplet lifetime of this dimer (4.7 ms), thus reinforcing the importance of this parameter. Comparisons between simulations and experiments reveal that the double-sensitization mechanism is part of the mechanism of intramolecular upconversion and that this additional pathway could be of great significance under specific conditions. The results from this study can thus act as a guide not only in terms of annihilator design but also for the design of future solid-state systems where intramolecular exciton migration is anticipated to play a major role.
- Olesund, Axel,Gray, Victor,M?rtensson, Jerker,Albinsson, Bo
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- Facile and fast pinacol rearrangement by AlCl3 in the solid state
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A facile and efficient synthetic procedure for effecting the pinacol rearrangement catalyzed by AlCl3 in the absence of solvent is developed. The rearrangement product is obtained at room temperature in a few minutes and in almost quantitative yield. Benzylic pinacols rearrange under these conditions, while aliphatic pinacols do not react.
- Rashidi-Ranjbar, Parviz,Kianmehr, Ebrahim
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- Effect of molecular conformation on the efficiency of the spin orbital charge recombination-induced intersystem crossing in bianthryls
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Two bianthryl dyads, with the two units connected at either the 2- or 9- positions of the anthryl moiety, were studied to establish the relationship between orientation of the anthryl moieties and the electronic coupling and intersystem crossing (ISC) efficiency. The anthryl moieties in the two dyads adopt a close-to-orthogonal geometry, with dihedral angles of 90° (9,9′-bianthryl) and 106° (2,9′-bianthryl) at the ground state, respectively. The charge transfer (CT) emission efficiency and the fluorescence lifetimes are clearly dependent on the electronic coupling between the two anthryls, and stronger coupling lead to higher fluorescence quantum yields (34% vs. 9%) and shorter luminescence lifetimes (13.9 ns vs. 38.6 ns). The bianthryl with more orthogonal geometry shows higher singlet oxygen quantum yields ΦΔ (9,9′-bianthryl, ΦΔ = 53%) than 2,9′-bianthryl (ΦΔ = 32%). Moreover, highly solvent polarity-dependent fluorescence emission and ΦΔ were observed for the dyads (ΦΔ = 22–53%), which is different from the trend of the monomer anthracene, thus we propose the spin-orbit charge transfer ISC (SOCT-ISC) is responsible for the triplet state productions of the dyads. Interestingly, we found that inducing a heavy atom (Br) does not increase the ISC yield of anthracene. ISC in bianthryls was also confirmed with nanosecond transient absorption spectroscopy, the featured T1→Tn absorption at ca. 433 nm was observed, and the triplet state lifetime are long (9,9′-bianthryl, τT = 353 μs; 2,9′-bianthryl, τT = 493 μs, in acetonitrile).
- Chen, Kepeng,Dong, Yu,Geng, Xinyu,Liu, Lang,Sukhanov, Andrey A.,Voronkova, Violeta K.,Zhao, Jianzhang,Zhao, Xiaoyu
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- Photoluminescence, redox properties, and electrogenerated chemiluminescence of twisted 9,9′-bianthryls
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To study the dual emission (from locally excited and charge transfer states) of sterically crowded 9,9′-bianthryl (BAHO) and its 10,10′-disubstituted derivatives, namely, 10,10′-dibromo-9,9′- bianthryl (BABR), 10,10′-bis(p-tolylethynyl)-9,9′-bianthryl (BAET), and 10,10′-bis(N,N-diphenyl-4-anilino)-9,9′-bianthryl (BATA) in detail, we probed their photophysical, redox, and electrogenerated chemiluminescence (ECL) responses. Dual emission for all of the molecules was noticed in PL, whereas in ECL only charge transfer emission was observed over a variety of experimental conditions. The PL in nonpolar solvents is significantly influenced by added supporting electrolyte, yielding exclusively charge transfer emission as in ECL. The stability of ECL proved to depend largely on the nature of the substituent, with triarylamine and bromo groups imparting constant ECL intensity over more than 60 cycles.
- Natarajan, Palani,Schmittel, Michael
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- A new thiosemicarbazone fluorescent probe based on 9,9′-bianthracene for Hg2+ and Ag+
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A new 9,9′-bianthracene-based thiosemicarbazone (D1) has been successfully synthesized and utilized for chemosensors. The properties of D1 were systematically investigated by UV–Vis, fluorescence titration and theoretical calculations. As a result, D1 exhibits a characteristic fluorescence quenching phenomenon in the presence of Hg2+ or Ag+ compared to other metal cations (Na+, K+, Mg2+, Ba2+, Al3+, Zn2+, Fe2+, Pb2+, Cu2+, Co2+, Cd2+, Ni2+ and Mn2+). The detection limits of Hg2+ and Ag+ reach 6.62 × 10?7 M and 1.99 × 10?5 M, respectively. This is mainly attributed to the Hg2+ (or Ag+) forms a stable five-membered ring with the N atom in Schiff base C[dbnd]N and the S atom in thiourea. The results suggest that the probe D1 is a promising candidate for chemosensors in aqueous media due to its highly selectivity for Hg2+ and Ag+.
- Chen, Zhen-E,Zhang, Hai,Iqbal, Zafar
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- Monomere Kupfer(I)-Alkyle mit β-Wasserstoffatomen und Kupfer(I)-Aryle mit kondensierten Aromaten; die Festkoerperstruktur von [(η5-C5H4SiMe3)2Ti(CCSiMe3)2]CunC4H9
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The synthesis of heterobimetallic titanium(IV)-copper(I) complexes of type {[Ti](CCSiMe3)2}CuR {3a, R=iC3H7; 3b, R=nC4H9; 3c, R=cC5H9; 3d, R=9-C13H9; 5a, R=1-C10H7; 5b, R=9-C14H9; [Ti]=(η5-C5H4SiMe3)2Ti} in which monomeric low-valent copper(I) organyls (CuR) are stabilised by the chelating effect of the organometallic ?-tweezer [Ti](CCSiMe3)2 are accessible by the reaction of {[Ti](CCSiMe3)2}CuSC6H4CH2NMe2-2 (1) with equimolar amounts of ER (E=Li, BrMg). These species feature monomeric copper alkyls or aryls, bearing -hydrogen atoms (complexes 3a-3c) or condensed aromatic ?-systems (complexes 5a and 5b). While 3a-3d, 5a and 5b are stable at low temperature in the solid-state, it appeared that in solution 3a-3c undergo β-hydride elimination, affording propene (3a), 1-butene (3b) or cyclopentene (3c). Next to these species, HSiMe3 (8) along with the dimeric titanium-copper acetylide {[Ti](CCSiMe3)(CuCC)}2 (6) is also formed. In contrast, 5b decomposes on heating (30 deg C) to afford the tweezer molecule [Ti](CCSiMe3)2 (9) and (C14H9)2 (10). Possible reaction mechanism for the latter reactions will be discussed. The solid-state structure of 3b is reported. Complex 3b crystallizes in the triclinic space group P1 with cell parameters a=13.659(2), b=17.270(3), c=18.106(4) Angstroem, α=107.64(3), β=100.11(3), γ=108.51(3) deg, Z=4 and V=3681(1) Angstroem3. The most striking structural feature of 3b, which will be discussed, is that the nC4H9 moiety is orientated out of the Ti(CCSi)2Cu plane.
- Stein, Thomas,Lang, Heinrich
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- Organotin reagents supported on ionic liquid: highly efficient catalytic free radical reduction of alkyl halides
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Ionic liquid-supported organotin reagents were prepared in good yield and demonstrated a convenient catalytic free radical reduction of alkyl halides. A variety of alkyl and aryl halides could be reduced in high to excellent yields and selectively to afford the desired products with simple work-up procedure.
- Pham, Phuoc Dien,Legoupy, Stéphanie
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- Co-crystals of 9,9′-bianthracene-10,10′-dicarboxylic acid with linear bidentate basic ligand molecules: Synthesis, crystal structure, and properties based on the layer structure exfoliated by water
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Co-crystals of 9,9′-dianthracene-10,10′-dicarboxylic acid (1) with the linear bidentate bases 9,9′-biacridine (bac), phenazine (phez), 4,4′-dipyridine (dpy), and DABCO (dabco) were synthesized. In the crystal structures of the co-crystals of 1 and bac, phez, and dpy, one-dimensional (1D) structures were formed through the hydrogen bonding between the acid and the base. For each combination of the acid and the bases, several kinds of polymorphic co-crystals with a similar structure were obtained. Among them, a combination of 1 and dabco gave three kinds of co-crystals which had a layered structure. In one of the co-crystals, a phenomenon where layers of the crystals could be exfoliated by dropping water was observed. The two-dimensional (2D) fingerprinting plot of the co-crystals showed that the major interaction to form the 1D structure was O-H?N hydrogen bonding and that to form the layered structure was the CH-π interaction, and the influence of the latter interaction on the robustness of the crystal was stronger than the former in the co-crystals.
- Azumaya, Isao,Hikawa, Hidemasa,Kikkawa, Shoko,Okayasu, Misaki
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- REACTIONS OF ANTHRACENE ANIONS WITH BERYLLIUM CHLORIDE
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Reaction of anthracene radical anion with BeCl2 in THF gives a crystalline polymeric organometallic compound that yields 9,9',10,10'-tetrahydro-9,9'-bianthryl (THBA) on hydrolysis.Hydrolysis with D2O gives exclusively trans-10-d, trans-10'-d hydrocarbon.Reaction of anthracene dianion with BeCl2 in THF leads to cleavage of the solvent and formation of cis-9,10-dihydro-9,10-bis(4-hydroxybutyl)anthracene.Comparable reactions of cyclooctatetraene dianion are also discussed.The results point up the covalence of the carbonberyllium bond.
- Berke, Carl M.,Streitwieser, Andrew
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- Two different charge transfer states of photoexcited 9,9'-bianthryl in polar and nonpolar solvents characterized by nanosecond time-resolved near-IR spectroscopy in the 4500-10 500 cm-1 region
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Transient absorption spectra of 9,9'-bianthryl (BA) in heptane, in acetonitrile, and in 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl) imide (bmimTf2N) are observed with a nanosecond time-resolved near-IR absorption spectrometer for the wavenumber range of 4500-10-500 cm -1(2200-950 nm). In nonpolar heptane solution, a broad absorption band is observed at 6700 cm-1(1500 nm), in addition to a strong absorption band of the locally excited (LE) state centered at 9800 cm -1(1020 nm). The broad band is assigned to a partial charge transfer (PCT) band. The decay time constants of the PCT band and the LE band are both (13 ±1) ns. The agreement of the two decay constants strongly suggests that the PCT state is in equilibrium with the LE state in heptane. In acetonitrile, an absorption band of the charge transfer (CT) state is observed at 8000 cm-1(1250 nm). This band decays in (41 ± 2) ns. In bmimTf2N, the CT band appears at 8500 cm-1(1180 nm) and decays in (34 ±1) ns. The difference in peak position for the CT bands in acetonitrile and in bmimTf2N, and the PCT bands in heptane, is explained well by the model based on the charge resonance between the two equivalent electronic structures of the CT state.
- Asami, Nobuyuki,Takaya, Tomohisa,Yabumoto, Soshi,Shigeto, Shinsuke,Hamaguchi, Hiro-O,Iwata, Koichi
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- Analysis of the solvatochromism of 9,9′-biaryl compounds using a pure solvent dipolarity scale
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The UV/vis absorption and fluorescence spectra of 9,9′-bisanthracenyl (BA), 9,9′- bisacridinyl (BAC), 9,9′-bicarbazyl (BC), and 9-(9′-anthracenyl)carbazole (C9A) were precisely recorded in solvents that change their solvent dipolarity scale (SdP) values from 0.000 (in 2-methylbutane at 293 K) to 1.294 (in 1-chlorobutane at 77 K). An analysis based (i) on the solvatochromic behavior of the four 9,9′-biaryl compounds in terms of the dipolarity of the solvents used, quantified by means of their SdP values, and (ii) on the behavior of the emission band profiles, allows the conclusion that, whereas the apolar 9,9′-biaryl compounds BA, BAC, and BC need solvents with SdP values larger than 0.74 to give a twisted intramolecular charge-transfer (TICT) process after excitation, for dipolar C9A the TICT mechanism is predominant already at solvent SdP values smaller than 0.23, i.e., near a solvent dipolarity of 0. The accuracy and simplicity achieved by application of the SdP scale in analyzing the solvatochromic behavior of the four 9,9′-biaryl compounds studied make evident the advantages of this solvent scale in comparison to other empirical solvent scales, which not only include the solvent's dipolarity but also consist of a more limited numerical range of values only.
- Catalan, Javier,Reichardt, Christian
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- Orthogonal Oriented Bisanthrancene-Bridged Bis(Triarylamine) Diradical Dications: Isolation, Characterizations and Crystal Structures
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Two bis(triarylamine) diradical dication salts 12+2[Al(ORF)4]? and 22+2[Al(ORF)4]? bridged with an orthogonal oriented bisanthrancene motif were synthesized. Their solid state and electronic structures were investigated by various experimental approaches in conjunction with theoretical calculations. Superconducting quantum interference device measurements and density functional theory calculations reveal that both of 12+ and 22+ feature open-shell singlet ground states with rather small singlet-triplet energy gaps; thus, they can be regarded as nearly pure diradicals (biradicals). Their diradical characters are enhanced by the orthogonal configuration of the bisanthrancene moiety which demonstrates the importance of the geometry of bridging units in turning the electronic structures of bis(triarylamine) dications.
- Wang, Lei,Zhang, Li,Fang, Yong,Zhao, Yue,Tan, Gengwen,Wang, Xinping
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- Pyrolysis of a tubular aromatic compound
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(Matrix presented) In the attempt to close the walls of a small tubular system that is a substructure of a [4,4] armchair nanotube a very unusual rearrangement reaction was observed.
- Deichmann,Naether,Herges, Rainer
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- Research on carbon-carbon coupling reactions of haloaromatic compounds mediated by zerovalent nickel complexes. Preparation of cyclic oligomers of thiophene and benzene and stable anthrylnickel(II) complexes
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Dehalogenative carbon-carbon coupling reactions of 3,4-dibromothiophene, 1,2-dihalobenzenes and 9-bromoanthracene using zerovalent nickel complexes as a dehalogenating reagent produced respectively cyclotetrathiophene, triphenylene and 9,9'-bianthracene in good yields.However, two extremely stable arylnickel(II) complexes, Ni(10-X-9-anthryl)X(PPh3)2 (X = Br, Cl), where the 10-C-X bond in the anthryl groups was inert against excess Ni0 complexes, were obtained by oxidative addition of 9,10-dihaloanthracenes to the Ni0 complexes.Under similar reaction conditions 9,10-dihaloanthracenes did not undergo carbon-carbon coupling reactions.
- Zhou, Zhen-hua,Yamamoto, Takakazu
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- On-Surface Synthesis and Characterization of Triply Fused Porphyrin–Graphene Nanoribbon Hybrids
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On-surface synthesis offers a versatile approach to prepare novel carbon-based nanostructures that cannot be obtained by conventional solution chemistry. Graphene nanoribbons (GNRs) have potential for a variety of applications. A key issue for their appli
- Mateo, Luis M.,Sun, Qiang,Liu, Shi-Xia,Bergkamp, Jesse J.,Eimre, Kristjan,Pignedoli, Carlo A.,Ruffieux, Pascal,Decurtins, Silvio,Bottari, Giovanni,Fasel, Roman,Torres, Tomas
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- Chromium- and Cobalt-Catalyzed, Regiocontrolled Hydrogenation of Polycyclic Aromatic Hydrocarbons: A Combined Experimental and Theoretical Study
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Polycyclic aromatic hydrocarbons are difficult substrates for hydrogenation because of the thermodynamic stability caused by aromaticity. We report here the first chromium- and cobalt-catalyzed, regiocontrolled hydrogenation of polycyclic aromatic hydrocarbons at ambient temperature. These reactions were promoted by low-cost chromium or cobalt salts combined with diimino/carbene ligand and methylmagnesium bromide and are characterized by high regioselectivity and expanded substrate scope that includes tetracene, tetraphene, pentacene, and perylene, which have rarely been reduced. The approach provides a cost-effective catalytic protocol for hydrogenation, is scalable, and can be utilized in the synthesis of tetrabromo- and carboxyl-substituted motifs through functionalization of the hydrogenation product. The systematic theoretical mechanistic modelings suggest that low-valent Cr and Co monohydride species, most likely from zerovalent transition metals, are capable of mediating these hydrogenations of fused PAHs.
- Han, Bo,Ma, Pengchen,Cong, Xuefeng,Chen, Hui,Zeng, Xiaoming
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p. 9018 - 9026
(2019/06/13)
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- Dianthranide-based compounds as well as preparation method and application thereof as high-pressure transducer
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The invention relates to dianthranide-based compounds as well as a preparation method and an application thereof as a high-pressure transducer. The compounds have molecular inner conformation continuously changing under pressure, have a broad pressure sensing range and can be used for pressure detection in different environments. The detection results of the compounds can be recognized in two modes including a spectral recognition mode and a chromatic recognition mode, and the dianthranide-based compounds can be used for detection by a spectrometer and by naked eyes.
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Paragraph 0051-0054
(2018/03/24)
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- Highly efficient dual anthracene core derivatives through optimizing side groups for blue emission
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TP-AA-TPB, TP-AA-TPB, TPB-AA-TPB, TP-AA-DPA, TP-AA-TPA, and TPB-AA-TPA were synthesized using a 9,9'-bianthracene (AA core). Through a systematic side group change, we optimized the dual-core chromophore system and investigated the relationship between the core and the side groups. The ultraviolet-visible (UV-Vis) absorption of the six materials showed an intrinsic absorption peaks of anthracene in the range of 360 nm–410 nm and photoluminescence (PL) emission in the blue region. The minimum decomposition temperatures (Td) was 425 °C, the minimum melting temperatures (Tm) was 335 °C, and the minimum glass transition temperatures (Tg) was 176 °C. We achieved excellent overall electroluminescence (EL) efficiency in non-doped OLED devices using the six synthesized materials as emitting layer (EML). TPB-AA-TPA synthesized through size and polarity optimization of the side groups on the AA core had a current efficiency of 8.97 cd/A, power efficiency of 4.43 lm/W, external quantum efficiency (EQE) of 6.37%, and Commission Internationale de L'Eclairage coordinates (CIE) of (0.14, 0.19). TPB-AA-TPA also maintained blue emission and realized the highest EL efficiency among the six synthesized materials.
- Lee, Hayoon,Jo, Minjin,Yang, Garam,Jung, Hyocheol,Kang, Seokwoo,Park, Jongwook
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- The anthracene derivatives, organic EL material and its manufacturing method (by machine translation)
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PROBLEM TO BE SOLVED: To provide an anthracene derivative in which a specific solubility radical is introduced into an anthracene skeleton, thereby improving solubility, and that is suitable to be used for film production in a solution process, and further to provide an anthracene derivative in which a specific solution radical of the anthracene derivative is desorbed by an external stimulation, and that is as an organic EL material excellent in characteristics.SOLUTION: For instance, anthracene derivatives (HTL1) and (HTL2) are exemplified to be synthesized by reaction formula (A). The anthracene derivative excellent in organic EL characteristics is obtained by the desorption of an ester group by an external stimulation.
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Paragraph 0164-0165
(2017/07/14)
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- Aryl Radical Geometry Determines Nanographene Formation on Au(111)
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The Ullmann coupling has been used extensively as a synthetic tool for the formation of C?C bonds on surfaces. Thus far, most syntheses made use of aryl bromides or aryl iodides. We investigated the applicability of an aryl chloride in the bottom-up assembly of graphene nanoribbons. Specifically, the reactions of 10,10′-dichloro-9,9′-bianthryl (DCBA) on Au(111) were studied. Using atomic resolution non-contact AFM, the structure of various coupling products and intermediates were resolved, allowing us to reveal the important role of the geometry of the intermediate aryl radicals in the formation mechanism. For the aryl chloride, cyclodehydrogenation occurs before dehalogenation and polymerization. Due to their geometry, the planar bisanthene radicals display a different coupling behavior compared to the staggered bianthryl radicals formed when aryl bromides are used. This results in oligo- and polybisanthenes with predominantly fluoranthene-type connections.
- Jacobse, Peter H.,van den Hoogenband, Adri,Moret, Marc-Etienne,Klein Gebbink, Robertus J. M.,Swart, Ingmar
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supporting information
p. 13052 - 13055
(2016/10/30)
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- Highly efficient deep-blue organic electroluminescent devices (CIE y ≈ 0.08) doped with fluorinated 9,9′-bianthracene derivatives (fluorophores)
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A series of new fluorinated 9,9′-bianthracene derivatives (BAnFs) have been designed and synthesized to serve as deep-blue dopants in organic electroluminescent (EL) devices. With the different substitution patterns of the electron-withdrawing groups, such as F and CF3, the photophysical properties, the energy levels and thermal stability of these BAnFs are tuned, which are supported by a density functional study of their geometry and electronic structure. In the thin film state, the fluorescent emissions of the BAnFs are fine-tuned from 448 to 439 nm, with varied fluorinated phenyl rings attached to the 9,9′-bianthracene core. All the BAnFs show a considerable thermal stability, which have high Tg values, above 150 °C. A pure blue emission at the Commission Internationale de l'Eclairage (CIE) coordinates (0.156, 0.083), has been achieved using the host 4,4′-bis(N-carbazolyl)biphenyl (CBP) doped with 10,10′-bis(3,5- bis(trifluoromethyl)phenyl)-9,9′-bianthracene (BAn-(3,5)-CF3). The maximum current efficiency and power efficiency of the BAn-(3,5)-CF 3-doped device are 3.05 cd A-1 and 2.62 lm W-1, corresponding to 5.02% of the maximum external quantum efficiency. The synthesized new fluorinated 9,9′-bianthracene derivatives show potential applications as highly efficient pure blue emitters for organic light emitting devices.
- Yu, Yue,Wu, Zhaoxin,Li, Zhanfeng,Jiao, Bo,Li, Lu,Ma, Lin,Wang, Dongdong,Zhou, Guijiang,Hou, Xun
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p. 8117 - 8127
(2014/01/06)
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- Process For Synthesis of 9,9'-Dianthracene
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This invention, which involves “the synthetic method of 9, 9′-biantnthracine”, belongs to the field of synthetic technology of organic electroluminesent materials. Synthetic method of 9, 9′-bianthracine is to add anthraquinone as raw material and zinc as reducing agent in glacial acetic acid solution, then batch addition of hydrochloric acid at 70-120°, maintain the temperature unchanged and react, then 9, 9′-bianthracine is achieved. This invention uses one-step method to synthesize 9, 9′-bianthracine, which reduces not only cost but also generation of side products, in addition, the products obtained need no purification and can be directly used to synthesize related similar compounds, therefore, it is very suitable for large-scale industrial production.
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(2012/03/27)
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- Process for Syntheis of 10,10-Dibromo-9,9-dianthracene
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This invention, which belongs to the field of organic electroluminesent materials synthetic technology, involves synthetic method of 10,10′-Dibromo-9,9′-bianthryl. The synthetic method is to use 9,9′-bianthryl as raw material, chlorinated hydrocarbon as solvent, bromide as bromine agent and react. This method not only produces no environmental pollution, but also enjoys high yield, therefore, it is suitable for industrial production.
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Page/Page column 2
(2012/03/27)
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- Electroluminescent Materials and Devices
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A hole transporting or hole conducting material for use in electroluminescent devices is a diamino dianthracene.
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- Short and efficient synthesis of coronene derivatives via ruthenium-catalyzed benzannulation protocol
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TpRuPPh3(CH3CN)2PF6 (3 mol %) was very active in catalytic benzannulation of 1-phenyl-2-ethynylbenzenes in dichloroethane (60 °C, 36 h) to afford phenanthrene in 95% yield. This method is applicable to the synthesis of various polycyclic aromatic hydrocarbons via two- and four-fold benzannulations, including various substituted coronene derivatives (53-86% yields) using this catalyst at a moderate loading (10 mol %).
- Shen, Hung-Chin,Tang, Jhih-Meng,Chang, Hsu-Kai,Yang, Chia-Wei,Liu, Rai-Shung
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p. 10113 - 10116
(2007/10/03)
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- Synthesis and optical properties of novel blue fluorescent conjugated polymers
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In the present paper we describe new approaches towards the synthesis of conjugated polymers with defined conjugation length, resulting in a blue or green fluorescence. The new approach reported here is to use 1,3-phenylene (type 1) and 10,10'-bianthrylene (type 2) bridges of conjugated segments such as stilbenes and thiophenes which can easily be varied to further change the optical properties.
- Baumgarten, Martin,Yueksel, Timucin
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p. 1699 - 1706
(2007/10/03)
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- Photochemisch induzierte Metathesereaktionen von Tetradehydrodianthracen: Synthese und Struktur von Bianthrachinodimethanen
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Keywords: Aromatizitaet; Brueckenkopfolefine; Cycloadditionen; Metathese; Polycyclen
- Kammermeier, Stefan,Herges, Rainer
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p. 470 - 472
(2007/10/03)
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- Thermolabile Hydrocarbons, 34. - Thermal Stability of 9,9'-Bixanthene and 9,9',10,10'-Tetrahydro-10,10,10',10'-tetramethyl-9,9'-bianthracene. - Stabilisation Energies of Planar Benzhydryl Radicals
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The thermal cleavage of the central CC bonds in the title compounds was investigated.The activation parameters were obtained from kinetics and the equilibrium enthalpies and entropies from the temperature dependence of the equilibrium radical concentrations, determined by quantitative ESR. ΔH(excit.) and ΔHDiss are nearly identical but not ΔS(excit.) and ΔSDiss, as expected.The radical stabilisation enthalpies RSE obtained from these data (RSE: 7a = 17.9+/-1.3; 7b = 15.6+/-1.4 kcal/mol) correspond closely to twice the RSE of α-phenylethyl radicals (8.0+/-1.5 kcal/mol) determined previously.The smaller RSE of the benzhydryl radical (12.9+/-0.9 kcal/mol), therefore, must be due to its nonplanarity. - Key Words: C-C Bond cleavage, energetics and kinetics of / Radicals, stability of / ESR
- Herberg, Clemens,Beckhaus, Hans-Dieter,Ruechardt, Christoph
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p. 2065 - 2072
(2007/10/02)
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- Electron Transfer and Ion Pair Formation, 34 Single Crystal Structure of the Solvent-Separated Ion Pair
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The one-electron transfer to large ?-delocalized hydrocarbons provides an interesting possibility to crystallize solvent-separated ion-pair salts containing optimally solvated cations.Accordingly, the reduction of 9,9'-bianthryl in aprotic 1,2-dimethoxyethane (DME) solution at a sodium metal mirror allows to grow dark blue, brick-like crystals of its radical anion and threefold DME-solvated sodium cation.The structure of the radical anion is very similar to that recently published for the neutral molecule.According to AM1 enthalpy hypersurface calculations based on the structural data, the torsion angle between 60 deg and 120 deg is determined by the lattice packing and the negative charge is ?-delocalized predominantly within only one anthracene subunit.The counter cation , reported only three times so far, shows a sixfold propeller-like coordination to approximate D3 skeletal symmetry with contact distances Na(1+)...O between 232 and 243 pm and angles ONa(1+)O varying between 69 deg and 159 deg.Due to the small repulsion between the chelating DME molecules, the isodesmically calculated Na(1+) solvation enthalpy is more negative than that of the analogous tetrahydrofuran complex - as confirmed by the laboratory experience that salts of less stable anions are preferentially crystallized from a strongly cation solvating DME solution. - Keywords: One-Electron Reduction of 9,9'-Bianthryl, Solvent-Separated Radical Ion Pair, Optimally Solvated Sodium Cation, Single Crystal Structure
- Bock, Hans,John, Andreas,Naether, Christian,Havlas, Zdenek
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p. 1339 - 1347
(2007/10/02)
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- Kinetic Study of the Multistep Reduction of 9,9'-Bianthryl in Superdry DMF and THF
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Cyclic and ac voltammetric studies of 9,9'-bianthryl/tetrabutylammonium perchlorate system (BA/TBAP) in superdry DMF and THF are presented.Kinetic parameters are obtained for the multistep reduction processes at the hanging mercury drop electrode, HMDE, and/or a Pt-disk electrode.The results of the electrode processes are found to be in agreement with the predictions of the Marcus theory for heterogeneous charge transfer reactions.Experimental data of DMF and THF are correlated and discussed. - Key words: Bianthryl / Electrode kinetics / Multiple step reduction
- Rashwan, Farouk
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p. 107 - 114
(2007/10/02)
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- SOME NEWER ASPECTS OF CLEMMENSEN REDUCTION OF AROMATIC KETONES
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9,9'-Bifluorenyl (6), 1,2,2,2-tetraphenylethane (10) and 10,10'-bianthrone (18) have been obtained as a new type of products in Clemmensen reduction of 9H-fluoren-9-one (3), benzophenone (7) and 9,10-anthraquinone (13) respectively.Dibenzochrysene (5) is formed as the major product in the reduction of 3.Plausible mechanistic pathways for the formation of the unconventional products have been delineated.
- Talapatra, Sunil K.,Chakrabarti, Syamal,Mallik, Asok K.,Talapatra, Bani
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p. 6047 - 6052
(2007/10/02)
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- Palladium(II)-Catalysed Aromatic Coupling and Substitution: Reactions of Anthracene, Phenanthrene, Diphenyl Ether and Diphenylamine
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Anthracene when refluxed with Pd(OAc)2 in glacial HOAc affords 9,9'-bianthranyl (1) in poor yield along with traces of para-anthracene (2), the major product being anthraquinone.Addition of small amount of HClO4 in the above reaction totally suppresses the coupling reaction and gives anthraquinone as the exclusive product in much better yield.Treatment of anthracene with Pd(OAc)2 in the presence of Pb(OAc)4 affords 9-acetoxyanthracene (4), anthraquinone and dianthrone (5).The observed divergence in the product profile with anthracene in the above reactions from those with its lower homologues has been rationalised.Intramolekular Pd(II)-catalysed aryl-aryl coupling reactions of diphenyl ether and diphenylamine have also been studied.It is observed that while the former is almost unreactive towards Pd(OAc)2 in HOAc, the latter is converted into carbazole in fairly good yield under identical reaction condition.
- Majumder, P. L.,Joardar, M.
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p. 1191 - 1193
(2007/10/02)
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- Reaction of Carbazolylpotassium with 9-Bromoanthracene and Nitrobenzene
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The formation of 9-(9-anthryl)carbazole (5) and 9-(2-nitrophenyl)anthracene (6) from 9-bromoanthracene (4), carbazole and nitrobenzene in the presence of potassium carbonate and catalytic amounts of copper is explained with the assumption of a trans-metallation equilibrium between carbazolylpotassium and nitrobenzene.
- Zander, Maximilian
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p. 3449 - 3451
(2007/10/02)
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- Nitrosamine Photolysis as a Synthetic Method: The Addition of Aminium Radicals to Unsaturated Carbon-Carbon Bonds
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Acid complexed nitrosamines decompose from their lowest singlet excited state to gine aminium radicals and nitric oxide radical transients.Aminium radicals initiate addition of various unsaturated groups to give 1-amino-2-nitroso compounds under an inert atmosphere, or 1-amino-2-nitrates under oxygen.In this report, photoaddition of nitroamines to olefins, acetylenes and fused aromatic hydrocarbons, and the subsequent transformations of the intermediates are described.Aminium radical initiated intramolecular cyclization to prepare tetracyclic aza compounds is also described.While photoaddition of nitrosamines to 4-propenylanisole or 3-butenol wes efficient, that to 3-butenyl benzoates under oxidative conditions was only fair, obviously due to the presence of a benzene ring.The oxidative photoaddition to 3-butenyl halide was followed by spontaneous cyclization to an azaspiro compound.The photoaddition to phenyl-substituted acetylenes gave β-nitroso enamines which hydrolyzed to diketomonoximes under neitral conditions but decomposed extensively under acidic conditions.Certain fused aromatic hydrocarbons acted as singlet sensitizers as well as substrates to induce similar addition giving amino nitroso adducts.These adducts took different courses of conversion dependent on reaction conditions, and on steric and electronic factors.
- Chow, Yuan L.,Colon, Carlos J.,Chang, Dawid W. L.,Pillay, K. Somasekharen,Lochart Robert D.,Tezuka, Takahiro
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p. 622 - 634
(2007/10/02)
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- Photochemical Reactions of Bromoanthracenes with N,N-Dimethylaniline in Solution
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Major products of the photolysis of 9-bromoanthracene and 9,10-dibromoanthracene in benzene and acetonitrile as well as photochemical reaction products of the two bromoanthracenes with N,N-dimethylaniline in these solvents have been isolated and identified.The mechanisms of partial reactions are discussed and attention is paid to the medium effect on the photochemical transformations. - Keywords: Photochemical Reactions, Bromoanthracenes
- Fulara, Jan,Latowski, Tadeusz
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p. 846 - 851
(2007/10/02)
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