- Synthesis, Photophysical and Supramolecular Properties of a π-Conjugated Molecular Crown Containing a Pentagonal Unit: A Model Compound for Fullerene C 240
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The total synthesis of carbon onions is a significant challenge in the fields of materials science and organic chemistry. To date, the synthesis of even a fragment of fullerene C 240and its smallest carbon onion C 60?C 240remains poorly explored. Herein, we demonstrate a bottom-up strategy to produce a novel π-extended molecular crown-shaped molecule (MC3) containing curved pentagonal and hexagonal units. This molecular crown represents a curved model compound for fullerene C 240and is fully characterized by NMR, mass spectrometry, UV-vis absorption, and from its emission spectra. Its supramolecular host-guest interaction with fullerene C 60is also investigated. MC3 and C 60?MC3 can potentially be employed as seeds or templates for the bottom-up synthesis of fullerene C 240and the carbon onion C 60?C 240, respectively.
- Du, Pingwu,Huang, Qiang,Liu, Huiqing,Wang, Jinyi,Wang, Shengda,Wu, Yayu,Zhou, Yu
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Read Online
- Synthesis of 7,12-bis(4-(di(1H-pyrrol-2-yl)methyl)phenyl)benzo[k]fluoranthene from a new dialdehyde as a novel fluorometric bis-Dipyrromethane derivative
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Dipyrromethanes are useful mediator structures which can be used as a part of other molecules such as bis-porphyrins and their derivations. Various methods have been developed for their synthesis. This study presents the synthesis of a new bis-dipyrrometh
- Ranjbari, Faride,Hemmati, Salar,Rashidi, Mohammad Reza
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- Catalytic Asymmetric (3 + 3) Cycloaddition of Oxyallyl Zwitterions with α-Diazomethylphosphonates
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The unique structure of oxyallyls represents a significant challenge for their catalytic asymmetric applications. Herein, an unprecedented chiral imidodiphosphoric acid-catalytic enantioselective (3 + 3) cycloaddition between oxyallyl zwitterions generate
- Liu, Yan,Peng, Xian,Peng, Yungui,She, Rui,Zhou, Xin
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supporting information
p. 7295 - 7300
(2021/10/01)
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- Cascade Ring-Opening Dual Halogenation of Cyclopropenones with Saturated Oxygen Heterocycles
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Represented is a CuX2- or I2-promoted ring-opening dual halogenation of cyclopropenones with saturated oxygen heterocycles, providing an efficient method for the synthesis of 3-haloacrylates. The ring-opening reaction enables the construction of two C–X (X = Cl, Br, or I) bonds and a C–O bond as well as the cleavage of two C–O bonds and a C–C bond in a single step. This protocol is highly atom economical, has an excellent substrate scope, and exhibits the ability for gram-scale reaction.
- Gao, Wen-Xia,Huang, Xiao-Bo,Liu, Miao-Chang,Miao, Wei-Hang,Wu, Hua-Yue,Zhou, Yun-Bing
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supporting information
p. 9425 - 9430
(2021/12/14)
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- Triphenylene-Enchained Perfluorocyclobutyl Aryl Ether Polymers: A Modular Synthetic Route to Processable Thermoplastics Approaching Upper Limit Tgand Photostability
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Triphenylene-containing trifluorovinyl ether monomers prepared from 2,3-disubstituted-bis-1,4-(p-bromophenyl)triphenylene core building blocks undergo thermal step-growth polymerization (Ph2O, 180 °C), affording perfluorocyclobutyl polymers with unprecede
- Athukorale, Sumudu,Borrego, Ernesto I.,Donnadieu, Bruno,Farajidizaji, Behzad,Jazi, Mehdi,Pittman, Charles U.,Smith, Dennis W.
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p. 7666 - 7672
(2021/09/02)
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- Amphiphilic Polyphenylene Dendron Conjugates for Surface Remodeling of Adenovirus 5
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Amphiphilic surface groups play an important role in many biological processes. The synthesis of amphiphilic polyphenylene dendrimer branches (dendrons), providing alternating hydrophilic and lipophilic surface groups and one reactive ethynyl group at the
- Krutzke, Lea,Landfester, Katharina,Li, Longjie,Müllen, Klaus,Mail?nder, Volker,Ng, David Y. W.,Simon, Johanna,Wagner, Jessica,Weil, Tanja,Wu, Yuzhou
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supporting information
p. 5712 - 5720
(2020/02/11)
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- GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE
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Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with a defect in glyoxylate metabolism, for example a disease or disorder associated with the enzyme glycolate oxidase (GO) or alterations in oxalate metabolism. Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.
- -
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Paragraph 001789; 001790
(2021/01/22)
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- Tetraaryl Cyclopentadienones: Experimental and Theoretical Insights into Negative Solvatochromism and Electrochemistry
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The synthesis of a series of tetraaryl cyclopentadienones comprising different substitution patterns is reported. Their photophysical and electrochemical properties are investigated by UV/Vis spectroscopy and cyclic voltammetry as well as by supporting quantum chemical simulations and reveal a distinct effect of substituents on the redox behavior of the molecules as well as the absorption properties of this class of compounds. While electrochemical data display a shift in reduction potential of up to 200 mV between the differently substituted cyclopentadienones, their photophysical investigations in differently polar solvents suggest a negative solvatochromic effect, although protic solvents induce a bathochromic shift. Crystal structure analyses of some derivatives confirm similarity with related cyclopentadienones while providing insight into intermolecular C–H···O and C–H···π interactions in the solid state.
- Meitinger, Nicolas,Mengele, Alexander K.,Witas, Kamil,Kupfer, Stephan,Rau, Sven,Nauroozi, Djawed
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p. 6555 - 6562
(2020/10/02)
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- From Alkyl Halides to Ketones: Nickel-Catalyzed Reductive Carbonylation Utilizing Ethyl Chloroformate as the Carbonyl Source
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Ketones are an important class of molecules in synthetic and medicinal chemistry. Rapid and modular synthesis of ketones remains in high demand. Described here is a nickel-catalyzed three-component reductive carbonylation method for the synthesis of dialkyl ketones. A wide range of both symmetric and asymmetric dialkyl ketones can be accessed from alkyl halides and a safe CO source, ethyl chloroformate. The approach offers complementary substrate scope to existing carbonylation methods while avoiding the use of either toxic CO or metal carbonyl reagents.
- Shi, Renyi,Hu, Xile
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supporting information
p. 7454 - 7458
(2019/04/30)
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- GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE
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Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme glycolate oxidase (GO). Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.
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Paragraph 001831; 001832; 001833
(2019/07/17)
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- Space-conjugated organic molecule based on hexaarylbenzene skeleton and preparation and application thereof
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The invention belongs to the technical field of organic electronics, and discloses a space-conjugated organic molecule based on a hexaarylbenzene skeleton and preparation and application thereof. Thespace-conjugated organic molecular structure based on th
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Paragraph 0040; 0043; 0045; 0053; 0056; 0064; 0065; 0074
(2018/11/22)
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- Organic electroluminescence material with electron transmission effect and organic light emitting device thereof
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The invention provides an organic electroluminescence material with an electron transmission effect and an organic light emitting device thereof, and belongs to the technical field of organic photoelectrical materials, which solves the technical problems of low light emitting efficiency, higher driving voltage, shorter service life and the like of the organic photoelectrical material in the prior art. Compared with the prior art, the organic electroluminescence material with the electron transmission effect and the organic light emitting device thereof have the advantages that the minimum driving voltage is 3.9V, the maximum light emitting efficiency is 21.4cd/A, and an excellent OLED (organic light emitting diode) material is provided.
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Paragraph 0037; 0039; 0047; 0049
(2017/10/22)
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- Synthesis and Characterization of Polycyclic Aromatic Hydrocarbons with Different Spatial Constructions Based on Hexaphenylbenzene Derivatives
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In recent years, low-bandgap polymers have attracted much attention in a wide range of fields. The synthesis of these compounds has been focused on three factors according to the Roncali bandgap theory: 1) the degree of bond-length alternation (Eδr), 2) the aromatic resonance energy of the cycle (ERes), and 3) the substituted groups (ESub). Herein, we have designed and prepared low-bandgap polymers in a different way by using the factors Eθ (the deviation from planarity of the polymer chain) and EInt (the interaction of the molecular chains in the solid state). Thus, three polycyclic aromatic hydrocarbons with different spatial constructions, based on hexaphenylbenzene derivatives, were prepared in this work: linear (P1-OX), V (P2-OX), and zigzag (P3-OX) types. These well-defined polymers exhibited interesting optical and electrochemistry behavior due to their different extents of planarity. Matrix-assisted laser desorption ionization time-of-flight mass spectrometry gave the incremental orderly molecular weight distributions of P1, P2, and P3, the weight-average molecular weights ((Formula presented.)) of which were 9000, 5500, and 69 000, respectively. Their lamellar layer structures and π–π intermolecular stacking were demonstrated by using two-dimensional grazing-incidence X-ray diffraction, which revealed the edge-on chain conformation. Finally, the materials were perfectly adapted to fabricate high-performance organic field-effect transistor devices, which revealed that these compounds could have great prospects as semiconductors.
- Chen, Hua,Zhu, Haoyun,Huang, Yuli,Yang, Junwei,Wang, Weizhi
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supporting information
p. 3016 - 3026
(2017/12/13)
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- Superbenzene-bridged bis(permethyl-β-cyclodextrin) as a convenient and effective probe for trinitrophenol exploder
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A novel planar C2 symmetrical superbenzene-bridged bis(permethyl-β-CD) was synthesized by grafting two permethyl-β-CD units onto a coronene core. Its self-assembly and luminescent behaviors could be smartly controlled by adjusting the polarity
- Yu, Jie,Chen, Yong,Li, Jing-Jing,Liu, Yu
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supporting information
p. 799 - 802
(2017/02/05)
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- Computational and Experimental Studies on the Effects of Monomer Planarity on Covalent Organic Framework Formation
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We report the synthesis of one new boronate ester-based covalent organic framework (COF) and two new covalent organic polymers (COPs) made with fluoranthene-containing monomers and hexahydroxytriphenylene. The structure of the monomer heavily influences w
- Thompson, Christina M.,Occhialini, Gino,McCandless, Gregory T.,Alahakoon, Sampath B.,Cameron, Victoria,Nielsen, Steven O.,Smaldone, Ronald A.
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p. 10506 - 10513
(2017/08/10)
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- DNA-Decorated Two-Dimensional Crystalline Nanosheets
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Design and synthesis of high aspect ratio 2D nanosheets with surface having ultradense array of information-rich molecule such as DNA is extremely challenging. Herein, we report a universal strategy based on amphiphilicity-driven self-assembly for the crafting of high aspect ratio, 2D sheets that are densely surface-decorated with DNA. Microscopy and X-ray analyses have shown that the sheets are crystalline. The most unique feature of the sheets is DNA-directed surface addressability, which is demonstrated through the decoration of either faces of the sheet with gold nanoparticles through sequence-specific DNA hybridization. Our results suggest that this design strategy can be applied as a general approach for the synthesis of DNA decorated high aspect ratio sheets, which may find potential applications in materials science, drug delivery, and nanoelectronics.
- Albert, Shine K.,Sivakumar, Irla,Golla, Murali,Thelu, Hari Veera Prasad,Krishnan, Nithiyanandan,Joseph Libin,Ashish,Varghese, Reji
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supporting information
p. 17799 - 17802
(2017/12/26)
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- Fluorene derivative and its preparation method
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The invention discloses 1 and 4-disubstituted fluorene and synthesis of cyclic derivative thereof. A preparation method of fluorene derivative comprises the following steps: a precursor compound 1 and 3-bis(4-bromine phenyl)-2-acetone or 1 and 3-bis(2-bromine phenyl)-2-acetone and ninhydrin are reacted to synthesize indene cyclopentadiene ketone derivative; and then 1 and 4-disubstituted fluorene derivative generated by a molecular conjugated system is magnified through Diels-Alder cyclic addition. 9-oxo-1 and 4-bis(4-bromine phenyl) fluorene, 9-oxo-1 and 4-bis(2-bromine phenyl) fluorene or 2-phenyl-4, 10-bis(4-bromine phenyl)-fluorene[1 and 2-f] isobenzazole-1, 3 and 5-triketone and 2- thiophene boric acid are reacted through the Suzuki reaction to generate the fluorene derivative containing terminated thiophene. As the fluorine derivative has good heat stability, the novel possibility is provided for exploring novel organic electroluminescence and solar cell materials.
- -
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Paragraph 0046; 0047; 0048; 0049
(2016/10/07)
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- COMPOSITION
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Provided is a composition which comprises two immiscible compounds and a compatibiliser, which stabilises the interface between two or more immiscible compounds. The compatibiliser improves the morphology of blends comprising the first and second compounds. The composition may be useful in the context of functional blends for optoelectronic applications, such as solar cells, organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs). Also provided is a process for the preparation of the composition and compounds for use therein.
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Page/Page column 22
(2016/12/22)
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- Assembly of twisted luminescent architectures based on acenaphtho[1,2-k]fluoranthene derivatives
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Acenaphtho[1,2-k]fluoranthene derivatives DPAF-n as new building blocks for one-dimensional (1D) structure assembly have been developed and employed to fabricate luminescent twisted nano/micro-wires; and the DPAF rigid core attached via flexible alkyl cha
- Han, Liang,Zhang, Yuewei,Chen, Weiping,Cheng, Xiao,Ye, Kaiqing,Zhang, Jingying,Wang, Yue
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supporting information
p. 4477 - 4480
(2015/03/18)
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- MULTIFUNCTIONAL MONOMERS AND THEIR USE IN MAKING CROSS-LINKED POLYMERS AND POROUS FILMS
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This invention is a monomer comprising at least two dienophile groups and at least two ring structures which ring structures are characterized by the presence of two conjugated carbon-to-carbon double bonds and the presence of a leaving group L, wherein L is characterized that when the ring structure reacts with a dienophile in the presence of heat or other energy sources, L is removed to form an aromatic ring structure. This invention is also curable oligomers and polymers and highly cross-linked polymers made with such monomers. Moreover, this invention is a method of making porous films by combining such monomers or their oligomers with a porogen, curing the polymer and removing the porogen.
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- Synthesis and proton conductivity of sulfonated, multi-phenylated poly(arylene ether)s
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A series of sterically-encumbered, sulfonated, poly(arylene ether) copolymers were synthesized and their proton conductivity examined. The series was prepared by copolymerizing a novel monomer, 2″,3″,5″, 6″-tetraphenyl-[1,1′:4',1″:4″,1″':4″', 1″″-quinquephenyl]-4,4″″-diol, with 4,4'- difluorobenzophenone and bisphenol A. Subsequent sulfonation and solution casting provided membranes possessing ion exchange capacities of 1.9 to 2.7 mmol/g and excellent mechanical properties (Young's modulus, 0.2-1.2 GPa; tensile strength, 35-70 MPa; elongation at break, 62-231%). Water uptake ranged from 34 to 98 wt% at 80 °C/100% RH. Proton conductivities ranged between 0.24 to 16 mS/cm at 80 °C/60% RH, and 3 to 167 mS/cm at 80 °C/95% RH. TEM analysis of the polymers, in the dehydrated state, revealed isolated spherical aggregates of ions, which presumably coalesce when hydrated to provide highly conductive pathways. The strategy of using highly-encumbered polymer frameworks for the design of mechanically-robust and dimensionally-stable proton conducting membranes is demonstrated. 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 2579-2587 Sulfonated, multiphenylated, random copolymers of poly(arylene ether)s were synthesized for examination as proton-conducting membranes. Proton conductivities ranged from 3 to 167 mS/cm at 80 °C/95% RH. The highly-encumbered polymer framework conferred exceptional mechanical strength and dimensional stability. Copyright
- Lee, Hsu-Feng,Wang, Po-Hsun,Huang, Yi-Chiang,Su, Wen-Hung,Gopal, Ram,Lee, Chun Che,Holdcroft, Steven,Huang, Wen-Yao
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p. 2579 - 2587
(2014/08/18)
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- Synthesis of 1,4-diarylfluorenone and 1,4-diarylfluorene
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A novel synthetic route to 1,4-diarylfluorenone and 1,4-diarylfluorene is presented by starting with ninhydrin. The retro-Diels-Alder cycloaddition was employed as a key step to construct the target fluorenones, while a highly efficient reduction from 1,4-diarylfluorenones to 1,4-diarylfluorenes is developed by using of sodium sulfide nonahydrate as reductant. The final products are confirmed by 1H NMR, 13C NMR and mass spectrometry.
- Wang, Yanmei,Liu, Qiancai,Xiong, Xiaoli,Deng, Shiming,Zhang, Jun,Zhu, Min,Ge, Hangmin
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p. 2333 - 2341
(2013/11/19)
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- Femtogram detection of explosive nitroaromatics: Fluoranthene-based fluorescent chemosensors
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Herein we report a novel fluoranthene-based fluorescent fluorophore 7,10-bis(4-bromophenyl)-8,9-bis[4-(hexyloxy)phenyl]fluoranthene (S3) and its remarkable properties in applications of explosive detection. The sensitivity towards the detection
- Venkatramaiah,Kumar, Shiv,Patil, Satish
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p. 14745 - 14751
(2013/01/15)
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- Convenient laboratory method for the synthesis of symmetrical 1,3-diphenylacetone derivatives
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A practical one-pot, two-step procedure for the synthesis of symmetrical 1,3-diphenylacetone derivatives from the corresponding phenylacetate has been developed. This procedure has been demonstrated by the synthesis of 1,3-diphenylacetone at the >50-gram scale in >99% purity. Georg Thieme Verlag Stuttgart - New York.
- Romer, Duane R.
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experimental part
p. 2721 - 2723
(2011/10/31)
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- Efficient synthesis of substituted polyarylphthalimides via cycloaddition of cyclopentadienones with 2-bromomaleimide
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Functionalized tetraarylphthalimides or diarylphthalimides fused with an acenaphthene moiety have been prepared in one step from 2-bromomaleimide and tetraarylcyclopentadienones (tetracyclones) or 7,9-diaryl-8H- cyclopentacenaphthylene-8-ones (acecyclones
- Vanel, Rémi,Berthiol, Florian,Bessières, Bernard,Einhorn, Cathy,Einhorn, Jacques
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supporting information; experimental part
p. 1293 - 1295
(2011/07/07)
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- Stepwise effective molarities in porphyrin oligomer complexes: Preorganization results in exceptionally strong chelate cooperativity
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Complexes of zinc porphyrin oligomers with multivalent ligands can be denatured by adding a large excess of a monodentate ligand, such as quinuclidine. We have used denaturation titrations to determine the stabilities of the complexes of a cyclic zinc-porphyrin hexamer with multidentate ligands with two to six pyridyl coordination sites. The corresponding complexes of linear porphyrin oligomers were also investigated. The results reveal that the stepwise effective molarities (EMs) for the third through sixth intramolecular coordination events with the cyclic hexamer are extremely high (EM = 10 2-103 M), whereas the values for the linear porphyrin oligomers are modest (EM ? 0.05 M). The speciation profiles for the denaturation reactions demonstrate that intermediate species are not significantly populated and that these equilibria are well described by a highly cooperative two-state model.
- Hogben, Hannah J.,Sprafke, Johannes K.,Hoffmann, Markus,Pawlicki, Milosz,Anderson, Harry L.
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supporting information; experimental part
p. 20962 - 20969
(2012/03/07)
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- Solid state conformational preferences of a flexible molecular backbone derived from acetone: Dependence on electron donating/withdrawing ability of substitutions
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Conformational preferences, crystal packing, and intermolecular interactions can play a pivotal role in solid state reactions, and in particular for bis(phenyl)acetones, these factors are known to determine the rate of the photodecarbonylation process. In
- Varughese, Sunil,Draper, Sylvia M.
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experimental part
p. 2298 - 2305
(2011/11/07)
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- Predicting the UV-vis spectra of tetraarylcyclopentadienones: Using DFT molecular orbital energies to model electronic transitions of organic materials
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(Chemical Equation Presented) Tetraphenylcyclopentadienone, due to its intrinsically low HOMO-LUMO gap, has been suggested as a valuable repeat unit in conducting polymers for nanoscale electronics. The HOMO and LUMO of tetraphenylcyclopentadienone appear
- Potter, Robert G.,Hughes, Thomas S.
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p. 2995 - 3004
(2008/09/19)
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- Thermal oxidation of tetracyclones (2,3,4,5-tetraarylcyclopentadienones)
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Tetracyclones are transformed to a mixture of diacylstilbenes and a-pyrones, when they are heated in diphenylether saturated with oxygen.
- Thiemann, Thies,Iniesta, Jesus,Walton, David J.
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experimental part
p. 173 - 180
(2009/05/07)
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- Synthesis of heterosubstituted hexaarylbenzenes via asymmetric carbonylative couplings of benzyl halides
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Asymmetric carbonylative couplings of benzyl halldes have been shown to give heterosubstituted 1,3-diarylacetones In moderate to high yields. These asymmetric ketones were converted via Knoevenagel condensations to tetraarylcyclopentadienones, and further
- Potter, Robert G.,Hughes, Thomas S.
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p. 1187 - 1190
(2008/01/04)
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- Hexaphenylbenzene derivatives for blue organic light-emitting devices
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Novel hexaphenylbenzene derivatives having high triplet energy levels were synthesized and used in blue organic electrophosphorescent devices. The device with a blue phosphorescent emitter, iridium(III) bis[(4,6-difluorophenyl) pyridinato-N,C2′
- Watanabe, Soichi,Kido, Junji
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p. 590 - 591
(2008/02/07)
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- Molecular tectonics. Construction of porous hydrogen-bonded networks from bisketals of pentaerythritol
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2,4,8,10-Tetraoxaspiro[5,5]undecanes tetrasubstituted at the 3 and 9 positions with groups incorporating diaminotriazines can be used for the construction of extensively hydrogen-bonded networks by the strategy of molecular tectonics. Four such compounds, tectons 1-4, were made by short and efficient syntheses involving bisketalization of pentaerythritol and subsequent reactions. Unlike tectons typically used in previous studies, compounds 1-4 are flexible and chiral, and they orient four sticky diaminotriazine groups in a distorted tetrahedral geometry. Tecton 1 crystallizes from DMF/toluene as an inclusion compound of approximate composition 1·8DMF·xH2O. In the resulting structure, each tecton participates in a total of 16 hydrogen bonds. Eight of these bonds involve four principal neighbors, and the tectons linked in this way define a distorted diamondoid network. Despite 8-fold interpenetration, 60% of the volume of the network is available for including guests. The guests are disordered and occupy parallel helical channels that have cross sections of approximately 11 × 12 A2 at the narrowest points. These channels provide access to the interior of the crystals and permit guests to be exchanged quantitatively without loss of crystallinity. It is noteworthy that tecton 1, despite its flexibility, small size, and structural simplicity, is apparently unable to find a periodic three-dimensional structure in which the dictates of hydrogen bonding and close packing are satisfied simultaneously.
- Sauriat-Dorizon, Helene,Maris, Thierry,Wuest, James D.,Enright, Gary D.
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p. 240 - 246
(2007/10/03)
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- Synthesis of 2-methyl-4, 6-diaryl-1, 2, 3-triazinones via diarylcyclopropenones
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2-Methyl-4,6-bis(4-substituted-phenyl)-1,2,3-triazin-5(2H)-ones 9a-d were prepared from the coressponding cyclopropenones 4a-d in a similar fashion as described by us previously. One of the the structure of 9b was established by an X-ray analysis.
- Matsumoto, Kiyoshi,Okada, Akihiro,Girek, Tomasz,Ikemi, Yukio,Kim, Jong Chul,Hayashi, Naoto,Yoshida, Hiroshi,Kakehi, Akikazu
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p. 325 - 328
(2007/10/03)
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- Synthesis and self-assembly of functionalized hexa-peri-hexabenzocoronenes
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Monolayers of hexa-alkyl substituted derivatives of hexa-peri-hexabenzocoronene (HBC) 1b have previously been investigated by scanning tunneling microscopy (STM) and scanning tunneling spectroscopy (STS). It is expected that different functional groups (electron donating or withdrawing) connected to the aromatic core will influence the packing pattern and possibly the current-voltage characteristics as well. In order to provide suitable model systems, a new synthetic approach to synthesize functionalized HBC derivatives has been developed. This was accomplished by [4+2]-cycloaddition of suitably bromo-substituted diphenyl-acetylenes and 2,3,4,5-tetraarylcyclo-penta-2,4-dien-1-ones followed by an oxidative cyclodehydrogenation with iron(III) chloride/nitromethane. Using this strategy three different substitution patterns were synthesized: 2-bromo-5,8, 11,14,17-pentadodecylhexa-peri-hexabenzocoronene (2a), 2,5-dibromo-8,11,14,17-pentadodecylhexa-peri-hexabenzocoronene (2b), and 2,11-dibromo-5,8,14,17-pentadodecylhexa-peri-hexabenzocoronene (2c). These bromo-substituted HBC derivatives were subjected to palladium catalyzed coupling reactions to give donor (alkoxy, amino) as well as acceptor (ester, cyano) substituted derivatives. The self-assembly of these new HBC derivatives was studied in the bulk as well as at an interface. DSC, optical microscopy, and X-ray diffraction revealed the existence of columnar mesophases. The bulk structure in the mesophase is largely insensitive to changes of the substitution pattern; however, in situ scanning tunneling microscopy at the solid-fluid interface between an organic solution of the HBC derivative and highly oriented pyrolytic graphite reveals different packing patterns of the first adsorbed monolayer.
- Ito, Shunji,Wehmeier, Mike,Diedrich Brand,Kuebel, Christian,Epsch, Rebekka,Rabe, Juergen P.,Muellen, Klaus
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p. 4327 - 4342
(2007/10/03)
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- Spherical polyphenylene dendrimers via Diels-Alder reactions: The first example of an A4B building block in dendrimer chemistry
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The [2+4]cycloaddition of the novel A4B building block 2,3,4,5-tetrakis(4-triisopropylsilylethynylphenyl)cyclopenta-2,4-dienone 3 with 3,3',5,5'-tetraethynylbiphenyl 1 allows the rapid synthesis of a spherical polyphenylene nanoparticle with 10
- Morgenroth, Frank,Berresheim, Alexander J.,Wagner, Manfred,Muellen, Klaus
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p. 1139 - 1140
(2007/10/03)
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- A Study of Substituent Effects on Hydrogen-to-Arene Nonbonded Interactions
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The polycyclic aromatic hydrocarbon 9,14-diphenylbenzotriphenylene is strongly twisted due to nonbonded interactions between hydrogen atoms on the polycyclic nucleus and the ? systems of the phenyl groups.Ten derivatives of 9,14-diphenylbenzotriphen
- L'Esperance, Robert P.,Engen, Donna Van,Dayal, Rajeev,Pascal, Robert A.
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p. 688 - 694
(2007/10/02)
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- IRON PENTACARBONYL MEDIATED COUPLING OF BENZYL HALIDES TO KETONES UNDER MILD PHASE TRANSFER CONDITIONS.
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In a two-phase system (saturated aqueous calcium hydroxide, tetrabutylammonium sulfate, dichloromethane, iron pentacarbonyl) benzyl bromides are readily carbonylated to dibenzyl ketones ; α-α' dibromoorthoxylene yields the o-quinodimethane iron tricarbonyl cmplex 8.It is inferred that the reactions proceed through transient generation of the tetracarbonyl ferrate dianion.
- Tanguy, Guy,Weinberger, Bernd,Abbayes, Hevre des
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p. 5529 - 5532
(2007/10/02)
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- ACTIVATED METALLIC NICKEL IN PREPARATION OF SYMMETRICAL 1,3-DIARYLPROPAN-2-ONES FROM BENZYLIC HALIDES AND OXALYL CHLORIDES
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Oxidative addition of benzylic halides to nickel in the metallic state followed by insertion of carbon monoxide generated from alkyl oxalyl chlorides proceeded smoothly to give symmetrical 1,3-diarylpropan-2-ones in moderate yields.
- Inaba, Shin-ichi,Rieke, Reuben D.
-
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- CATALYTIC PHASE TRANSFER CARBONYLATION OF BENZYL HALIDES WITH IRON PENTACARBONYL.
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Benzyl halides are readily carbonylated to arylacetic acids in a two-phase system (aqueous sodium hydroxide (1M), tetrabutylammonium sulfate ; organic phase (CH2Cl2 or C6H6 or C6H5CH3)), using a catalytic amount of the cheap, easy to handle iron pentacarbonyl under carbon monoxide atmosphere.
- Tanguy, Guy,Weinberger, Berndt,Abbayes, Herve des
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p. 4005 - 4008
(2007/10/02)
-