- Synthesis, Structures, and Optoelectronic Properties of Pyrene-Fused Thioxanthenes
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A series of pyrene-fused thioxanthenes have been synthesized via a new concise route, and their crystal structures and photophysical properties have been fully investigated. The eight-ring fused dipyrene-thioxanthene (DPTA) can crystallize to monoclinic and triclinic X-ray structures, and their precursor has been isolated as two stable atropisomers with different photophysical properties. The EHOMO becomes higher and the Eg become narrower as more thioxanthene unit being fused with pyrene.
- Zhang, Shiqian,Liu, Zhiqiang,Fang, Qi
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- Preparation and luminescence properties of isoquinoline-nucleated polycyclic aromatics
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Two isoquinoline-nucleated polycyclic aromatic compounds, 4,5-diphenyl-7H-dibenzo[de,g]quinolin-7-one (A) and 3,4-diphenyl-6H-phenanthro[3,4,5-defg]quinolin-6-one (B), were synthesized in high yields through three-component reaction of phenanthrene diketone or pyrene diketone, ammonium acetate and 1,2-diphenylethyne in one-pot. Their structures, thermal stabilities, photophysical properties and energy levels are investigated systematically. Both compounds emit very weak fluorescence in acetone, but their luminescence intensity increased significantly when the water content reaches 50% for A and 40% for B, exhibiting aggregation-induced emission (AIE) characteristics, and showing that the AIE effect of the compound A is stronger than that of the compound B. The vacuum-processed doped devices based on the compound B showed green emission with a maximum brightness of 2162 cd/m2, a maximum current efficiency of 2.97 cd/A and a maximum external quantum efficiency (EQE) of 2.23%.
- Li, Yanmei,Li, Xinyu,Yu, Tianzhi,Su, Wenming,Wang, Youjia,Zhao, Yuling,Zhang, Hui
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- Pyrenoimidazole-based deep-blue-emitting materials: Optical, electrochemical, and electroluminescent characteristics
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A series of pyrenoimidazoles that contained various functional chromophores, such as anthracene, pyrene, triphenylamine, carbazole, and fluorene, were synthesized and characterized by optical, electrochemical, and theoretical studies. The absorption spectra of the dyes are dominated by electronic transitions that arise from the pyrenoimidazole core and the additional chromophore. All of the dyes exhibited blue-light photoluminescence with moderate-to-high quantum efficiencies. They also displayed high thermal stability and their thermal-decomposition temperatures fell within the range 462-512 °C; the highest decomposition temperature was recorded for a carbazole-containing dye. The oxidation propensity of the dyes increased on the introduction of electron-rich chromophores, such as triphenylamine or carbazole. The application of selected dyes that featured additional chromophores such as pyrene, carbazole, and triphenylamine as blue-emissive dopants into multilayered organic light-emitting diodes with a 4,4′-bis(9H-carbazol-9-yl)biphenyl (CBP) host was investigated. Devices that were based on triphenylamine- and carbazole-containing dyes exhibited deep-blue emission (CIE 0.157, 0.054 and 0.163, 0.041), whereas a device that was based on a pyrene-containing dye showed a bright-blue emission (CIE 0.156, 0.135). Deep-blue something: New pyrenoimidazoles showed blue emission with a high quantum efficiency and thermal stability and low oxidation potential. The 10-pyrenyl pyrenoimidazole gave a driving voltage of 5.3 eV and a brightness of 2736 cd m-2. Copyright
- Kumar, Dhirendra,Thomas, K. R. Justin,Lin, Ching-Chiao,Jou, Jwo-Huei
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- Synthesis of Pyrene-4,5-dione on a 15 g Scale
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A scalable and efficient method for the synthesis of pyrene-4,5-dione has been developed. The addition of N-methylimidazole (NMI, 5 mol-%) to a known oxidation reaction was shown to marginally improve the yield and dramatically improve the ease of the workup and thus the amount of product isolable in a day by using regular laboratory equipment.
- Walsh, Joshua C.,Williams, Kerry-Lynn M.,Lungerich, Dominik,Bodwell, Graham J.
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- Two pyrene-based S-containing atropisomers: Different structures and different Ag+-response behaviors of their monomer-excimer emission
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Different structures and different Ag+-response behaviors of a pair of pyrene-based S-containing atropisomers, namely s-BSPPy and a-BSPPy, have been investigated. The calculated high rotation barrier indicates that the two atropisomers are non-interconvertible. In polar solvents, s-BSPPy exhibits excimer emission but a-BSPPy does not. Based on the X-ray structures and the DFT calculated intermolecular interactions, the excimer of s-BSPPy is suggested to take a non-parallel edge-to-face λ-shaped geometry. Especially, s-BSPPy exhibits ratiometric excimer-off and monomer-on emission as a unique response to Ag+ in solutions, while no ratiometric Ag+-response was observed for a-BSPPy.
- Jin, Ying-ying,Fang, Qi,Zhang, Shi-qian,Liu, Zhi-qiang
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- Highly efficient deep-blue organic light-emitting diodes based on pyreno[4,5-d] imidazole-anthracene structural isomers
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High-efficiency deep-blue luminophores, especially those satisfying the National Television Standards Committee (NTSC) blue standard Commission Internationale de l'éclairage (CIE) coordinates of (0.14, 0.08), are vital for full-color displays and solid-state illumination. However, deep-blue luminescent materials with efficient photoluminescence quantum yields (φPLs) and high external quantum efficiencies (EQEs) over 5% remain very limited. Imidazole has shown great potential in optoelectronic fields owing to its ambipolar nature. Combining imidazole with rigid aromatic rings, such as naphthalene, phenanthrene and pyrene, could effectively enlarge the π-electronic delocalization, reduce non-radiative transitions of molecules and ensure high φPLs in the solid-state. Herein, two symmetrically twisted pyreno[4,5-d]imidazole-anthracene structural isomers, 9,10-bis(4-(10-phenyl-9H-pyreno[4,5-d]imidazol-9-yl)phenyl)anthracene (N-BPyIA) and 9,10-bis(4-(9-phenyl-9H-pyreno[4,5-d]imidazol-10-yl)phenyl)anthracene (C-BPyIA), have been designed and synthesized by connecting one anthracene group with two pyreno[4,5-d]imidazole groups at the N1 and the C2 position, respectively. They both show high φPLs in neat films (46% for N-BPyIA and 54% for C-BPyIA), good thermal stabilities (Td > 541 °C), and appropriate energy levels for carrier injection. N-BPyIA shows better performance than C-BPyIA when applied in OLEDs. The non-doped device based on N-BPyIA shows sky blue emission with CIE coordinates of (0.22, 0.31), achieving a high EQE of 5.63% with a low efficiency roll-off. In particular, a doped device with better performance is further realized, providing an EQE of 7.67% and deep-blue emission (CIE (0.15, 0.10)), which is very close to the NTSC standard. Such high OLED efficiency may be ascribed to triplet energy harvesting by triplet-triplet annihilation. And to our best knowledge, this is one of the best outcomes of deep-blue imidazole-based fluorescent OLEDs. The results also pave the way for a new type of high-efficiency deep-blue organic luminescent materials regulated by structural isomerization.
- Liu, Hui,Kang, Liangliang,Li, Jinyu,Liu, Futong,He, Xin,Ren, Shenghong,Tang, Xiangyang,Lv, Changli,Lu, Ping
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- Relationship Between Molecular Structure, Single crystal Packing and Self-Assembly Behavior: A Case Based on Pyrene Imide Derivatives
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Development of new n-type one-dimensional (1D) self-assembly nanostructure and a clear understanding of the relationship between molecular structure and self-assembly behavior are important prerequisites for further designing and optimizing organic optoelectronic nanodevice. In this article, a series of n-type organic semiconductor materials based on pyrene imide were successfully synthesized through [4+2] cycloaddition reactions and their preliminary optical and electrochemical properties were studied. The simulated HOMO-LUMO bandgaps via DFT tallied with the experimental data well. The self-assembly of these materials showed needle or fiber-like morphologies, indicating that different conjugation degree or alkyl group had significant influence on their self-assembly behaviors. Furthermore, the single-crystal packing for these molecules were analyzed and it was found out that the changes of conjugated backbone and functional group would affect certain crystal lattice parameter significantly, such as the intermolecular packing distance and crystal size etc, which would further result in different self-assembly morphology.
- Chen, Jiawen,Chen, Wangqiao,Han, Hongjing,Li, Xiaojun,Qiu, Meizhen,Zhang, Qichun,Zhang, Shilong
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supporting information
(2021/12/08)
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- A Three-Step Synthesis of 4H-Cyclopenta[def]phenanthrene from Pyrene
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4H-Cyclopenta[def]phenanthrene (CPP) is a valuable building block in the production of photoactive polymers, which find use in a wide range of organic electronic applications. Of particular importance is their use in the development of blue-colored, organic light-emitting diodes (OLEDs), which remains a challenge in the field. Unfortunately, commercial sources and synthetic procedures known in the literature are unable to provide enough CPP for large scale implementation. Herein, we report on the development of a novel, gram-scale synthesis of CPP in three steps, starting from pyrene. The key steps in our methodology are the ring contraction of pyrene-4,5-dione to oxoCPP in a single step, as well as the direct reduction of oxoCPP to CPP. Apart from the small number of synthetic steps, our methodology benefits from the use of relatively non-hazardous reagents, together with optimized purification procedures, making CPP accessible in useful quantities.
- Filippov, Dmitri V.,Overkleeft, Hermen S.,Schneider, Grégory F.,van der Ham, Alex
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supporting information
p. 2013 - 2017
(2021/06/25)
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- Fluorescence Sensors for Bismuth (III) Ion from Pyreno[4,5-d]imidazole Derivatives
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Three pyreno[4,5-d]imidazole derivatives are synthesized and evaluated as fluorescent sensors for bismuth (III) ion. The target compounds are prepared in 55–86% yields from a condensation reaction between pyrene-4,5-dione and aromatic aldehydes. The compound bearing a phenolic group can selectively detect bismuth (III) ion via fluorescence enhancement with a detection limit of 1.20?μm in CH3CN-DMSO mixture and 3.40?μm in 10% pH5 aqueous in CH3CN-DMSO mixture. The sensing mechanism involving a formation of coordination complex is investigated by UV-VIS and fluorescence titrations, 1H-NMR and the decomplexation of the bismuth complex by sulfide ion. The application of this sensor for quantitative analysis of spiked bismuth (III) ion in real water samples from two different sources is demonstrated.
- Chanawungmuang, Nichapa,Sukwattanasinitt, Mongkol,Rashatasakhon, Paitoon
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p. 301 - 308
(2020/10/06)
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- Pyrenedione-Catalyzed α-Olefination of Nitriles under Visible-Light Photoredox Conditions
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Herein, we report a combination of pyrenedione (PD) and KOtBu to achieve facile alcohol dehydrogenation under visible-light excitation, where aerobic oxygen is utilized as the terminal oxidant. The resulting carbonyl compound can be easily converted to vinyl nitriles in a single-pot reaction, at 60 °C in 6-8 h. This environmentally benign, organocatalytic approach has distinct advantages over transition-metal-catalyzed α-olefination of nitriles, which often operate at a significantly higher temperature for an extended reaction time.
- Bains, Amreen K.,Ankit, Yadav,Adhikari, Debashis
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supporting information
p. 2019 - 2023
(2021/04/05)
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- Sterically driven metal-free oxidation of 2,7-di-tert-butylpyrene
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We disclose an unprecedented single-step metal-free green oxidation of 2,7-di-tert-butylpyrene selectively into either the corresponding 4,5-dione or 4,5,9,10-tetraone, two key building blocks used for organic optoelectronic applications using hypervalent
- Cesario, Marcello F.,El-Assaad, Tarek H.,McGrath, Dominic V.,Parida, Keshaba N.
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p. 5966 - 5971
(2020/10/18)
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- Synthesis, Photophysical and Electronic Properties of New Red-to-NIR Emitting Donor–Acceptor Pyrene Derivatives
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We synthesized new pyrene derivatives with strong bis(para-methoxyphenyl)amine donors at the 2,7-positions and n-azaacene acceptors at the K-region of pyrene. The compounds possess a strong intramolecular charge transfer, leading to unusual properties such as emission in the red to NIR region (700 nm), which has not been reported before for monomeric pyrenes. Detailed photophysical studies reveal very long intrinsic lifetimes of >100 ns for the new compounds, which is typical for 2,7-substituted pyrenes but not for K-region substituted pyrenes. The incorporation of strong donors and acceptors leads to very low reduction and oxidation potentials, and spectroelectrochemical studies show that the compounds are on the borderline between localized Robin-Day class-II and delocalized Robin-Day class-III species.
- Merz, Julia,Dietz, Maximilian,Vonhausen, Yvonne,W?ber, Frederik,Friedrich, Alexandra,Sieh, Daniel,Krummenacher, Ivo,Braunschweig, Holger,Moos, Michael,Holzapfel, Marco,Lambert, Christoph,Marder, Todd B.
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p. 438 - 453
(2019/11/26)
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- Strong Enhancement of π-Electron Donor/Acceptor Ability by Complementary DD/AA Hydrogen Bonding
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π-Conjugated organic materials possess a wide range of tunable optoelectronic properties which are dictated by their molecular structure and supramolecular arrangement. While many efforts have been put into tuning the molecular structure to achieve the desired properties, rational supramolecular control remains a challenge. Here, we report a novel series of supramolecular materials formed by the co-assembly of weak π-electron donor (indolo[2,3-a]carbazole) and acceptor (aromatic o-quinones) molecules via complementary hydrogen bonding. The resulting polarization creates a drastic perturbation of the molecular energy levels, causing strong charge transfer in the weak donor–acceptor pairs. This leads to a significant lowering (up to 1.5 eV) of the band gaps, intense absorption in the near-IR region, very short π-stacking distances (≥3.15 ?), and strong ESR signals in the co-crystals. By varying the strength of the acceptor, the characteristics of the complexes can be tuned between intrinsic, gate-, or light-induced semiconductivity with a p-type or ambipolar transport mechanism.
- Liu, Cheng-Hao,Niazi, Muhammad Rizwan,Perepichka, Dmitrii F.
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supporting information
p. 17312 - 17321
(2019/11/16)
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- Evolution of physical and photocatalytic properties of new Zn(II) and Ru(II) complexes
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Synthesis of Zn(II) and Ru(II) complexes were reported by using N4-macrocyclic Schiff base ligands under solvothermal conditions. The newly synthesized Zn(II) and Ru(II) complexes have been characterized by various physico-chemical techniques such as elemental analysis, molar conductance, HRMS, TGA, FESEM, UV–Vis, FT-IR, 1H NMR, and cyclic voltammetry. By using molar conductance studies, the complexes are formulated as [Zn(TPTTP)]Cl2 and [Ru(TPTTP)Cl2]. C–H bond activation of an sp3 group of methylstyrenes (converted into cinnamaldehydes) and C–H bond activation of the sp2 bond of polycyclic aromatic hydrocarbons through photooxidation was examined in the presence of Zn(II) and Ru(II) complexes. Reusable activity studies and photostability of catalyst are investigated by using UV–Vis spectra. Based on the results, higher catalytic activity of [Ru(TPTTP)Cl2] complex than [Zn(TPTTP)]Cl2 complex in both C–H bond activation and photooxidation of aromatic hydrocarbons has been reported.
- Gugulothu, Venkanna,Ahemed, Jakeer,Subburu, Mahesh,Yadagiri, Bhongiri,Mittal, Ritu,Prabhakar, Chetti,Pola, Someshwar
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p. 412 - 423
(2019/06/27)
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- Controlled deposition of large-area and highly-ordered thin films: effect of dip-coating-induced morphological evolution on resistive memory performance
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Developing a simple, versatile and efficient technique that enables both large-scale production and nano-scale control is highly desirable but very challenging for achieving high-performance organic-based memory electronic devices. Herein, we employed a dip-coating method to fabricate reliable and cost-effective organic memory devices (OMDs). This technique enables us to deposit high-quality, homogeneous and large-area nanopatterns on the surfaces of thin films and realize uniform OMD performances with a record reproducibility up to 96%. To the best of our knowledge, this is the first report on dip-coated OMDs with the highest reproducibility observed to date, which demonstrates the promising versatility of the dip-coating technique to fabricate organic memory devices and its suitability to scale-up for high-throughput solution processing.
- Li, Yang,Zhang, Cheng,Li, Zhuang,Gu, Peiyang,Wang, Zilong,Li, Hua,Lu, Jianmei,Zhang, Qichun
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supporting information
p. 3512 - 3521
(2019/03/27)
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- Synthesis, fluorescence properties, and conformational analysis of ether-linked (1,8)pyrenophanes
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Mono-, di- and oligo-ether linked (1,8)pyrenophanes 1–7 were synthesized, and their fluorescence and conformational properties in the absence and presence of metal ions were elucidated. Fluorescence spectra of 1.0 × 10?5 M solutions of the mono- and di-ether linked pyrenophanes 1–5 were comprised of only monomer emission bands, while those of the oligoethylene glycol linked analogs 6 and 7 contained both monomer and intramolecular excimer emission bands. Addition of perchlorate salts of Ba2+, Na+ and Li+ to 1:1 v/v CH3CN:CH2Cl2 solutions of 6 and 7 caused decreases in the intensities of the corresponding intramolecular excimer emission bands and, in some cases, increases in the intensities of the monomer emission. Monomer and intramolecular excimer emission from the (1,8)pyrenophanes are suggested to arise from the respective anti and syn conformers, whose ratios are dependent on solvent polarity, temperature and kinds of added metal ions.
- Maeda, Hajime,Geshi, Makoto,Hirose, Kenji,Furuyama, Taniyuki,Segi, Masahito
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- A novel organic semiconductor material, preparation method, the field effect transistor device and manufacturing method thereof (by machine translation)
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A novel organic semiconductor material, preparation method, the field effect transistor device and manufacturing method thereof, relates to a photoelectric material field, as the basic framework by pi, using the same synthetic strategy, design, to synthesize a new kind of semiconductor material. Model of the semiconductor material in the form of a solid 365 nm ultraviolet light under different colors of emitted red light. By thermal vapor deposition and solution method to construct the field effect transistor device. The construction of the thin film field effect device exhibits a different electric charge transmission performance. (by machine translation)
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Paragraph 0054-0059
(2019/07/10)
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- Copper(i)-based oxidation of polycyclic aromatic hydrocarbons and product elucidation using vacuum ultraviolet spectroscopy and theoretical spectral calculations
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Copper(i) complexes supported by fluorinated 1,3,5-triazapentadienyl ligands have been used as catalysts for the oxidation of anthracene, naphthalene, and pyrene to the corresponding quinones, using H2O2 as an oxidant under mild conditions without an acid co-catalyst. Gas chromatography-vacuum ultraviolet spectroscopy (GC-VUV) combined with time-dependent density functional theory theoretical computations of absorption spectra was demonstrated as a new and useful tool-set for unknown determination in complex reaction mixtures, especially when standards are not available for spectral comparisons and product mixtures involve closely related isomers. The anthracene has been converted to 9,10-anthraquinone in quantitative yield using this copper catalyzed process. The oxidation of naphthalene afforded 1,4-naphthoquinone as the major product, and 1-naphthol and 2-naphthol as minor products. The pyrene oxidation resulted in 4,5-, 1,6-, and 1,8-pyrenequinones, among other products. The X-ray crystal structure of [N{(CF3)C(C6F5)N}2]CuNCCH3 is also reported.
- Ponduru, Tharun T.,Qiu, Changling,Mao, James X.,Leghissa, Allegra,Smuts, Jonathan,Schug, Kevin A.,Dias, H. V. Rasika
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supporting information
p. 19442 - 19449
(2018/12/13)
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- Mechanistic Insights into Selective Oxidation of Polyaromatic Compounds using RICO Chemistry
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Ruthenium-ion-catalyzed oxidation (RICO) of polyaromatic hydrocarbons (PAHs) has been studied in detail using experimental and computational approaches to explore the reaction mechanism. DFT calculations show that regioselectivity in these reactions can be understood in terms of the preservation of aromaticity in the initial formation of a [3+2] metallocycle intermediate at the most-isolated double bond. We identify two competing pathways: C?C bond cleavage leading to a dialdehyde and C-H activation followed by H migration to the RuOx complex to give diketones. Experimentally, the oxidation of pyrene and phenanthrene has been carried out in monophasic and biphasic solvent systems. Our results show that diketones are the major product for both phenanthrene and pyrene substrates. These diketone products are shown to be stable under our reaction conditions so that higher oxidation products (acids and their derivatives) are assigned to the competing pathway through the dialdehyde. Experiments using 18O-labelled water do show incorporation of oxygen from the solvents into products, but this may take place during the formation of the reactive RuO4 species rather than directly during PAH oxidation. When the oxidation of pyrene is carried out using D2O, a kinetic isotope effect (KIE) is observed implying that water is involved in the rate-determining step leading to the diketone products.
- Nowicka, Ewa,Hickey, Niamh W.,Sankar, Meenakshisundaram,Jenkins, Robert L.,Knight, David W.,Willock, David J.,Hutchings, Graham J.,Francisco, Manuel,Taylor, Stuart H.
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supporting information
p. 12359 - 12369
(2018/08/29)
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- Zinc-Containing Radical Anions via Single Electron Transfer to Donor–Acceptor Adducts
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Reactions of [Cp*2Fe] with the Lewis acid [Zn(C6F5)2] in the presence of [(PhC(S)S)2], 9,10-phenanthrenedione or 4,5-pyrenedione yield the salt [Cp*2Fe][(PhC(S)S)Zn(C6F5/su
- Cao, Levy L.,Bamford, Karlee L.,Liu, Liu Leo,Stephan, Douglas W.
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supporting information
p. 3980 - 3983
(2018/03/05)
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- Oxidation of Polynuclear Aromatic Hydrocarbons using Ruthenium-Ion-Catalyzed Oxidation: The Role of Aromatic Ring Number in Reaction Kinetics and Product Distribution
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Oxidation of aromatic hydrocarbons with differing numbers of fused aromatic rings (2–5), have been studied in two solvent environments (monophasic and biphasic) using ruthenium-ion-catalyzed oxidation (RICO). RICO reduces the aromaticity of the polyaromatic core of the molecule in a controlled manner by selective oxidative ring opening. Moreover, the nature of the solvent system determines the product type and distribution, for molecules with more than two aromatic rings. Competitive oxidation between substrates with different numbers of aromatic rings has been studied in detail. It was found that the rate of polyaromatic hydrocarbon oxidation increases with the number of fused aromatic rings. A similar trend was also identified for alkylated aromatic hydrocarbons. The proof-of-concept investigation provides new insight into selective oxidation chemistry for upgrading of polyaromatic molecules.
- Nowicka, Ewa,Clarke, Tomos J.,Sankar, Meenakshisundaram,Jenkins, Robert L.,Knight, David W.,Golunski, Stanislaw,Hutchings, Graham J.,Willock, David J.,Francisco, Manuel,Taylor, Stuart H.
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p. 655 - 662
(2018/01/26)
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- A [...] derivative and its synthetic method and application (by machine translation)
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A [...] derivative and its synthetic method and application, mainly related to the field of semiconductor material. Above pi to pi synthesis of imide derivative of the first non-active site (4, 5, 9, 10 bit) oxidation, and through the bromine atom substituted, methoxy, cyano substituted, hydrolysis, the operator and other reaction, introduced with electron withdrawing ability of the imide, pyrazine and halogen group, synthesizing a series of novel has good electronic capture ability of [...] derivatives, so that the [...] derivatives used in the non-volatile organic field effect transistor memory in a device, demonstrated better photoelectric performance and memory performance; in addition, the above [...] derivative synthesis method also has the simple preparation method, the step is short, high yield and the like. Therefore, the above-mentioned [...] derivative and its synthetic method and application possesses the important value of popularization and application. (by machine translation)
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Paragraph 0041; 0043
(2018/11/03)
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- Hexyl substituted - fluorenylmethylchloroformate modified aryl imidazole compound, preparation method and its darkblue photoelectric electroluminescent device (by machine translation)
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The invention belongs to the organic light-emitting material and its photoelectric device application technology field, in particular to hexyl substituted - fluorenylmethylchloroformate modified aryl imidazole compound, preparation method and its darkblue photoelectric electroluminescent device. The invention provides a hexyl substituted - fluorenylmethylchloroformate modified aryl imidazole compounds and its preparation method, the substituted states the hexyl - fluorenylmethylchloroformate modified aryl imidazole compound of the general formula formula I structure. The invention also provides based on hexyl substituted - fluorenylmethylchloroformate modified aryl imidazole compound can be efficient transmitting deep-blue light-emitting electroluminescent device, solves the difficult to give consideration to the prior art high blue light purity and connects escape efficiency the technical problem of, by means of the imidazole material with hexyl fluorene fine characteristic, synthetic which has both a high soluble, high blue light purity and a high fluorescence quantum yield of the organic light-emitting small molecule and its dark blue light organic electroluminescent device. (by machine translation)
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Paragraph 0071; 0080; 0081; 0082
(2018/07/15)
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- White-Fluorescent Dual-Emission Mechanosensitive Membrane Probes that Function by Bending Rather than Twisting
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Bent N,N′-diphenyl-dihydrodibenzo[a,c]phenazine amphiphiles are introduced as mechanosensitive membrane probes that operate by an unprecedented mechanism, namely, unbending in the excited state as opposed to the previously reported untwisting in the ground and twisting in the excited state. Their dual emission from bent or “closed” and planarized or “open” excited states is shown to discriminate between micelles in water and monomers in solid-ordered (So), liquid-disordered (Ld) and bulk membranes. The dual-emission spectra cover enough of the visible range to produce vesicles that emit white light with ratiometrically encoded information. Strategies to improve the bent mechanophores with expanded π systems and auxochromes are reported, and compatibility with imaging of membrane domains in giant unilamellar vesicles by two-photon excitation fluorescence (TPEF) microscopy is demonstrated.
- Humeniuk, Heorhii V.,Rosspeintner, Arnulf,Licari, Giuseppe,Kilin, Vasyl,Bonacina, Luigi,Vauthey, Eric,Sakai, Naomi,Matile, Stefan
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supporting information
p. 10559 - 10563
(2018/08/17)
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- Novel riboflavin-inspired conjugated bio-organic semiconductors
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Flavins are known to be extremely versatile, thus enabling routes to innumerable modifications in order to obtain desired properties. Thus, in the present paper, the group of bio-inspired conjugated materials based on the alloxazine core is synthetized using two efficient novel synthetic approaches providing relatively high reaction yields. The comprehensive characterization of the materials, in order to evaluate the properties and application potential, has shown that the modification of the initial alloxazine core with aromatic substituents allows fine tuning of the optical bandgap, position of electronic orbitals, absorption and emission properties. Interestingly, the compounds possess multichromophoric behavior, which is assumed to be the results of an intramolecular proton transfer.
- Richtar, Jan,Heinrichova, Patricie,Apaydin, Dogukan Hazar,Schmiedova, Veronika,Yumusak, Cigdem,Kovalenko, Alexander,Weiter, Martin,Sariciftci, Niyazi Serdar,Krajcovic, Jozef
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- Phototransformations of environmental contaminants in models of the aerosol: 2 and 4-Nitropyrene
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A comparative photochemical study of 2- and 4-nitropyrene (2- and 4-NO2Py) in different organic solvents was performed in order to provide information on the fate of these contaminants in models of the atmospheric aerosols. The isomers presented small photodegradation yields, 10?4–10?5 for 4-NO2Py and 10?5–10?6 for 2-NO2Py, demonstrating the low reactivity of the excited states and intermediate species that participate in their photodegradation. Photoproducts such as 4,5-pyrenedione, 4-hydroxypyrene, aminopyrene and pyrene were identified during the irradiation of 4-NO2Py. Substantial differences were observed in the photodegradation yields, and type and relative yields of the photoproducts of the 2-NO2Py and 4-NO2Py when compared to those of 1-NO2Py. These differences were related with the orientation of the nitro group and with differences in intersystem crossing rates which affect the yields of the pyrenoxy radical (PyO) and of the (π,π*) triplet state, principal precursors in their photodegradation. The smallest photodegradation yield was for 2-NO2Py due to the lack of interaction between the nitro group and the aromatic moiety thus resulting in a low yield of formation of the PyO radical. In the presence of O2, the photodegradation quantum yields of 4-NO2Py were reduced in all solvents due the quenching of the (π,π*) triplet state, and 4-aminopyrene was not observed thus demonstrating that its formation occurs from this state. These results suggest that in atmospheric aerosols containing an organic liquid-like layer, the nitropyrene isomers will show low photoreactivity resulting in an increase in their residence time in the atmosphere. An increase in reactivity is expected when the excited nitropyrenes are nearby substances with hydrogen donor capacities such as phenols. The photoproducts formed in the transformation could increase the toxicity of the particulate matter in the atmosphere.
- García-Berríos, Zulma I.,Arce, Rafael,Burgos-Martínez, Melanie,Burgos-Polanco, Natalia D.
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p. 131 - 140
(2016/09/07)
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- The K-Region in Pyrenes as a Key Position to Activate Aggregation-Induced Emission: Effects of Introducing Highly Twisted N,N-Dimethylamines
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A new design strategy to activate aggregation-induced emission (AIE) in pyrene chromophores is reported. In a previous report, we demonstrated that highly twisted N,N-dialkylamines of anthracene and naphthalene induce drastic AIE when these donors are introduced at appropriate positions to stabilize the S1/S0 minimum energy conical intersection (MECI). In the present study, this design strategy was applied to pyrene: the introduction of N,N-dimethylamine substituents at the 4,5-positions of pyrene, the so-called K-region, are likely to stabilize MECIs. To examine this hypothesis, four novel pyrene derivatives, which contain highly twisted N,N-dimethylamino groups at the 4- (4-Py), 4,5- (4,5-Py), 1- (1-Py), or 1,6-positions (1,6-Py) were tested. The nonradiative transitions of 4,5-Py are highly efficient (knr = 57.1 × 107 s-1), so that its fluorescence quantum yield in acetonitrile decreases to φfl = 0.04. The solid-state fluorescence of 4,5-Py is efficient (φfl = 0.49). In contrast, 1,6-Py features strong fluorescence (φfl = 0.48) with a slow nonradiative transition (knr = 11.0 × 107 s-1) that is subject to severe quenching (φfl = 0.03) in the solid state. These results underline that the chemistry of the pyrene K-region is intriguing, both from a photophysical perspective and with respect to materials science.
- Sasaki, Shunsuke,Suzuki, Satoshi,Igawa, Kazunobu,Morokuma, Keiji,Konishi, Gen-Ichi
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p. 6865 - 6873
(2017/07/17)
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- Organic electroluminescent material and organic electroluminescent device
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The invention provides an organic electroluminescent material and an organic electroluminescent device. The organic electroluminescent material is a pyrene-substituting benzimidazole class organic electroluminescent material with a structure shown as formula I, belongs to a three line state - three line state amalgamation (TTA) material, and has the advantages of high luminous efficiency, excellent thermal stability and balanced charge transport properties. The light-emitting layer of the electroluminescent device comprises a host material and a guest material which belong to TTA mechanism class materials of similar molecular structures, and the organic electroluminescent device exhibits very high brightness and high external quantum efficiency under high brightness, and shows a great application potential.
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Paragraph 0070; 0071; 0072
(2018/02/04)
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- Pyrene and imidazole derivative and preparation method and application thereof
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The invention relates to a pyrene and imidazole derivative and a preparation method and application thereof. The bridging mode of C2 atom and N1 atom of an imidazole group is changed to form the pyrene and imidazole derivative with the structural formula as shown in (A), the pyrene and imidazole derivative is a novel blue-light emitting material, and owing to introduction of the imidazole group, the level structure and the electron transmission performance of the pyrene and imidazole derivative can be regulated. The pyrene and imidazole derivative can serve as an organic electroluminescent material to prepare an organic electroluminescent device, and the prepared device has the characteristics of high efficiency, low driving voltage and the like.
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Paragraph 0082; 0083; 0103; 0104; 0108; 0109
(2017/09/18)
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- Derivative containing bispyrenyl imidazole, and preparation method and application thereof
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The invention relates to a derivative containing bispyrenyl imidazole, and a preparation method and an application thereof. The bridging mode of the C2 atom and the N1 atom in an imidazolyl group is changed o form the derivative containing bispyrenyl imidazole, the structure of the derivative containing bispyrenyl imidazole is represented by formula (A) or formula (B), the derivative containing bispyrenyl imidazole is a novel blue light material, and the imidazolyl group is introduced to adjust the energy level structure and the electron transport property of the above compound. The derivative containing bispyrenyl imidazole can be used for making organic electroluminescent device as an organic electroluminescent material, and the made devices have the characteristics of high brightness, high efficiency and low driving voltage.
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Paragraph 0019; 0080
(2017/08/31)
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- Ruthenium nanoparticles supported on mesoporous MCM-41 as an efficient and reusable catalyst for selective oxidation of arenes under ultrasound irradiation
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Mesoporous MCM-41 was used as a support for the uniform dispersion of ruthenium nanoparticles having an average particle size of ~5 nm. The obtained nanocomposite, MCM-41-Ru, was characterized using inductively coupled plasma, transmission electron microscopy, energy dispersive X-ray analysis, X-ray diffraction, and BET surface area measurements. The material was employed as an efficient and recyclable catalyst in the ultrasound-assisted oxidation of arenes. It was observed that ultrasound irradiation in combination with KBrO3 as the oxidant, in the presence of MCM-41-Ru nanoparticles, accelerates the oxidation reaction to afford the desired products in good yields. The recovered catalyst retained activity for successive runs, with a continuous change in the nature of its active sites.
- Khorshidi, Alireza
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p. 153 - 158
(2016/01/12)
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- Solution-processable thiadiazoloquinoxaline-based donor-acceptor small molecules for thin-film transistors
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Although several [1,2,5]thiadiazolo[3,4-g]quinoxaline (TQ)-thiophene-based hybrid polymers have been demonstrated for application in organic field-effect transistors (OFETs), the research on the charge carrier mobility of conjugated donor (D)-acceptor (A) small molecules is rare. To enrich the TQ-containing small molecule family, in this paper, we designed and synthesized three novel TQ derivatives 1, 2, and 3 with thiophene units attached onto the TQ cores. The optoelectronic and OFET properties of as-prepared compounds 1-3 are investigated. Our results indicate that compounds 1-3 show typical p-type characteristics with mobility as high as 0.012, 0.05 and 0.0055 cm2 V-1 s-1 and on/off current ratios of 3 × 105, 1 × 106 and 1 × 104 under the optimized conditions, respectively. Due to the steric effect of the substituted bulky group, compound 3 adopts a looser packing mode with a larger π-π distance, which subsequently reduces the transport performance. Our results suggest that the D-A π-conjugated small molecules based on TQ could be good candidates for application in organic electronic devices.
- Gu, Pei-Yang,Zhang, Jing,Long, Guankui,Wang, Zilong,Zhang, Qichun
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supporting information
p. 3809 - 3814
(2016/05/19)
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- A supramolecular strategy based on molecular dipole moments for high-quality covalent organic frameworks
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A supramolecular strategy based on strong molecular dipole moments is presented to gain access to covalent organic framework structures with high crystallinity and porosity. Antiparallel alignment of the molecules within the pore walls is proposed to lead to reinforced columnar stacking, thus affording a high-quality material. As a proof of principle, a novel pyrene dione building block was prepared and reacted with hexahydroxytriphenylene to form a boronic ester-linked covalent organic framework. We anticipate the strategy presented herein to be valuable for producing highly defined COF structures.
- Salonen, Laura M.,Medina, Dana D.,Carbó-Argibay, Enrique,Goesten, Maarten G.,Mafra, Luís,Guldris, Noelia,Rotter, Julian M.,Stroppa, Daniel G.,Rodríguez-Abreu, Carlos
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supporting information
p. 7986 - 7989
(2016/07/06)
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- N-Rich Fused Heterocyclic Systems: Synthesis, Structure, Optical and Electrochemical Characterization
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A new class of N-rich fused heterocyclic compounds containing the triazolo-triazine moiety was synthesized and studied by cyclic voltammetry, UV/Vis spectroscopy, X-ray diffraction, and first principle computations. All the compounds show reversible or quasi-reversible reduction processes, with reduction potentials easily tunable within the class. LUMO energies as low as -3.95 eV have been measured. The UV/Vis spectra show highly structured absorptions, indicative of rigid molecular skeletons. The solid-state packing is dominated by π-π stacking interactions, which are promoted by weak CAr-H···N interactions, whereas face-to-edge contacts (T contacts), typical of many fused hydrocarbons, are largely absent.
- Fusco, Sandra,Maglione, Cira,Velardo, Amalia,Piccialli, Vincenzo,Liguori, Rosalba,Peluso, Andrea,Rubino, Alfredo,Centore, Roberto
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p. 1772 - 1780
(2016/04/05)
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- Substituted dibenzo[FG,OP]tetracenes and formulations or electronic devices containing the same
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The present invention is directed to a compound of the formula (2) and its uses thereof: wherein T, U, V and W is CR1; R1 is H; X, is CR2 and N with the proviso that at least one X is equal to CR2 and at least one R2 from CR2 is equal to Z; and n and m are 0, 1, 2, 3 to 4 and either n is at least 3 or m is at least 3.
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Page/Page column 131
(2015/05/26)
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- ELECTRODE ACTIVE MATERIAL FOR ELECTRICITY STORAGE DEVICE, AND ELECTRICITY STORAGE DEVICE USING SAME
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The present invention provides an electrode active material for an electricity storage device, having a structure represented by following formula (1). In the formula (1), R1 to R6 each denote independently a hydrogen atom (except for a case where all of R1 to R6 denote hydrogen atoms), a halogen atom, an optionally substituted phenyl group, an optionally substituted heterocyclic group, or an optionally substituted hydrocarbon group having 1 to 4 carbon atoms.
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- Visible light-harvesting cyclometalated Ir(III) complexes with pyreno[4,5-d]imidazole C^N ligands as triplet photosensitizers for triplet-triplet annihilation upconversion
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Cyclometalated Ir(III) complexes with pyrenyl-fused imidazole ligands were prepared. The complexes show strong absorption of visible light and long-lived triplet excited state and were used as triplet photosensitizers for triplet-triplet annihilation (TTA) upconversion. Pyreno[4,5-d]imidazole C^N ligand was used to access the long-lived T1 excited state (Ir-1, bpy = 2,2′-bipyridine as the N^N ligand. τT = 56.1 μs). In order to enhance the absorption in visible range, a coumarin derived N^N ligand was used (Ir-2, ε = 51,500 M-1 cm-1 at 466 nm, τT = 73.9 μs). The complexes show room temperature phosphorescence in the red. The T1 excited states of Ir-1 and Ir-2 were identified as mainly intraligand (3IL) states, vs. the metal-to-ligand-charge-transfer (3MLCT) state for the model complex (Ir-0), proved by steady state emission, transient absorption, 77 K emission spectra and DFT calculations. The complexes were used as triplet photosensitizers for TTA upconversion and upconversion quantum yield up to 23.7% was observed.
- Yi, Xiuyu,Yang, Pei,Huang, Dandan,Zhao, Jianzhang
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p. 104 - 115,12
(2020/08/20)
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- 1,8-pyrenylene-ethynylene macrocycles
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Chemical equations presented. A concise, highly regioselective synthesis of 1,8-dibromo-4,5-dialkoxypyrenes has been developed and exploited in the synthesis of some 1,8-pyrenylene-ethynylene macrocycles. The 1H NMR data and NICS calculations indicate that there is little or no macrocyclic ring current. Concentration-dependent UV-visible studies indicate no aggregation at low concentration, but 8b forms dimers with voids suitable for intercalation of small molecules in the solid state.
- Venkataramana, Gandikota,Dongare, Prateek,Dawe, Louise N.,Thompson, David W.,Zhao, Yuming,Bodwell, Graham J.
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supporting information; experimental part
p. 2240 - 2243
(2011/06/22)
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- Synthesis of π-extended thiadiazole (oxides) and their electronic properties
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The syntheses of extended thiadiazole, thiadiazole oxide, and thiadiazole dioxide heterocycles are described. The electron-accepting heterocycles were investigated by X-ray crystallography and optical as well as electrochemical measurements and supported by DFT calculations. The thiadiazole dioxide heterocycles have reduction potentials of -0.7 V vs ferrocene/ferrocenium, suggesting a viable building block for n-type organic materials.
- Linder, Thomas,Badiola, Eider,Baumgartner, Thomas,Sutherland, Todd C.
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supporting information; experimental part
p. 4520 - 4523
(2010/12/25)
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- A rigid molecular balance for measuring face-to-face arene-arene interactions
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(Chemical Equation Presented) A new molecular balance was developed to measure face-to-face arene-arene interactions. The balance adopts distinct folded and unfolded conformations due to restricted rotation about a C aryl-Nimlde bond. In the folded conformer, the rigid bicyclic framework enforces an offset face-to-face geometry to the exclusion of edge-to-face geometries, which was verified by X-ray crystallography. Measurement of the folded to unfolded ratio yields accurate values for the arene-arene interaction in a range of different solvents.
- Carroll, William R.,Pellechia, Perry,Shimizu, Ken D.
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supporting information; experimental part
p. 3547 - 3550
(2009/05/07)
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- Ruthenium(III) chloride catalyzed oxidation of pyrene and 2,7-disubstitued pyrenes: An efficient, one-step synthesis of pyrene-4,5-diones and pyrene-4,5,9,10-tetraones
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(Chemical Equation Presented) Pyrene and 2,7-disubstituted pyrenes have been oxidized with ruthenium(III) chloride (RuCl3) and sodium periodate (NaIO4) under very mild conditions to 4,5-diones or 4,5,9,-10-tetraones. Thus, the oxidation has been controlled by varying the amount of oxidant and reaction temperature to proceed exclusively at the pyrene 4- and 5-positions or at the 4-, 5-, 9-, and 10-positions.
- Hu, Jie,Zhang, Dong,Harris, Frank W.
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p. 707 - 708
(2007/10/03)
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- Resolution and Absolute Configuration of K-Region Trans Dihydrodiols from Polycyclic Aromatic Hydrocarbons
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K-region trans dihydrodiols of benzophenanthrene, chrysene, pyrene, and dibenzacridine have been resolved as their diastereomeric diesters with (-)-(menthyloxy)acetic acid, and their absolute configuration have been assigned by the application of circular dichroism and excition chirality methods.For these as well as the K-region trans dihydrodiol derivatives from five other hydrocarbons, a consistent pattern of physical properties has emerged.The R,R diastereomers are less retained on silica gel HPLC columns when eluted with ether-cyclohexane mixtures and show negative values of D in tetrahydrofuran, the degree of magnetic nonequivalence between HA and HB in the -OCHAHBCO2- portion of the diesters (100 MHz, C6D6) is generally much higher for the S,S enantiomers of the dihydrodiols, and the free R,R dihydrodiols have positive values of D in tetrahydrofuran provided their hydroxyl groups do not have a marked preference for the pseudodiaxial conformation.
- Balani, S. K.,Bladeren, P. J. van,Shirai, N.,Jerina, D. M.
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p. 1773 - 1778
(2007/10/02)
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- IODOXYBENZENE A REMARKABLY CLOSE OZONE EQUIVALENT
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Iodoxybenzene is isoelectronic to ozone and several of its reactions proceed via pathways remarkably similar to that of ozone.An attractive feature of iodoxybenzene mediated reactions is the direct formation of products and the transformation of the reagent to iodobenzene.The formation of benzil and iodobenzene in good yields from diphenylacetylene provides support for the anticipated intermediate arising from ?4s+?2s addition.Iodoxybenzene transforms phenanthrene to phenanthrenequinone as a result of the initially formed 4+2 adduct undergoing C-H rupture, in preference to the C-C rupture.This change is parallel to the transformation of phenanthrene 9-carboxylic acid to phenanthrenequinone with ozone.The expected C-C rupture of the initially formed adduct does take place with acenaphthylene leading to naphthalic anhydride.The reaction of pyrene with iodoxybenzene leads to nearly equal amounts of the 4-5, 1-6 and 3-6 quinones involving attack on the bond of the lowest bond localisation energy and the atom of the lowest atom localization energy.This behaviour is similar to the action of ozone on benzopyrene.Iodoxybenzene transforms anthracene, just like ozone, to anthraquinone, in good yields.The involvement of transannular addition of iodoxybenzene, as is partly the case with ozone, is proved unlikely by reaction with 9, 10 dimethylanthracene which gave 10-methyl 9-anthraldehyde and 10-carboxy 9-anthraldehyde, involving the insertion of elements of iodoxybenzene to the aryl C-H bond.This tendency of iodoxybenzene has been further demonstrated by the following changes: diphenylmethane-->benzophenone; fluorene-->fluorenone and tetralin-->α-tetralone.Several of the transformations brought about with iodoxybenzene provide attractive synthetic routes, particularly to phenanthrenequinone, pyrenequinones and tetralone.Finally, just like the 2O3 --> 3O2 change, iodoxybenzene, and even more so, 4-iodoxybiphenyl, thermally fragment to iodobenzene and 4-iodobiphenyl.
- Ranganathan, S.,Ranganathan, D.,Ramachandran, P. V.
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p. 3145 - 3152
(2007/10/02)
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- Reaction of Polycyclic Aromatic Hydrocarbons with Ozone. Linear Free-Energy Relationships and Tests of Likely Rate-Determining Steps Using Simple Molecular Orbital Correlations
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Nine unsubstituted, polycyclic aromatic hydrocarbons were allowed to react with ozone at 25 deg C, and relative rate constants were obtained by direct competitive techniques.The rate constants show a large variation with substrate structure, with nearly three powers of ten difference between the least reactive (benzene) and most reactive (anthracene, perylene) compounds studied.Linear free-energy relationships between the rate data and calculated molecular orbital parameters have been obtained.The optimum correlations are found for models based on rate-determining ?-complex or ?-complex formation rather than simultaneous addition of ozone to two carbon atoms.Electrophilic attack by ozone to yield a ?-complex also appears to be the rate-determining step based on the results obtained for changes in selectivity with variation of solvents.
- Pryor, William A.,Gleicher, Gerald J.,Church, Daniel F.
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p. 4198 - 4202
(2007/10/02)
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