- Single-molecule conductance of dibenzopentalenes: antiaromaticity and quantum interference
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The effects of antiaromaticity and destructive quantum interference (DQI) are investigated on the charge transport through dibenzo-[a,e]pentalene (DBP). 5,10-Connectivity gives high single-molecule conductance whereas 2,7 gives low conductance due to DQI. Comparison of the 5,10-DBP with phenyl and anthracene analogues yields the trend GDBP ≈ GAnth > GPh, despite the aromatic anthracene having a larger HOMO-LUMO gap than 5,10-DBP. This is explained by unfavourable level alignment for 5,10-DBP. This journal is
- Schmidt, Maximilian,Wassy, Daniel,Hermann, Mathias,González, M. Teresa,Agr?it, Nicolás,Zotti, Linda A.,Esser, Birgit,Leary, Edmund
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Read Online
- Iron-Catalyzed Vinylzincation of Terminal Alkynes
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Organozinc reagents are among the most commonly used organometallic reagents in modern synthetic chemistry, and multifunctionalized organozinc reagents can be synthesized from structurally simple, readily available ones by means of alkyne carbozincation. However, this method suffers from poor tolerance for terminal alkynes, and transformation of the newly introduced organic groups is difficult, which limits its applications. Herein, we report a method for vinylzincation of terminal alkynes catalyzed by newly developed iron catalysts bearing 1,10-phenanthroline-imine ligands. This method provides efficient access to novel organozinc reagents with a diverse array of structures and functional groups from readily available vinylzinc reagents and terminal alkynes. The method features excellent functional group tolerance (tolerated functional groups include amino, amide, cyano, ester, hydroxyl, sulfonyl, acetal, phosphono, pyridyl), a good substrate scope (suitable terminal alkynes include aryl, alkenyl, and alkyl acetylenes bearing various functional groups), and high chemoselectivity, regioselectivity, and stereoselectivity. The method could significantly improve the synthetic efficiency of various important bioactive molecules, including vitamin A. Mechanistic studies indicate that the new iron-1,10-phenanthroline-imine catalysts developed in this study have an extremely crowded reaction pocket, which promotes efficient transfer of the vinyl group to the alkynes, disfavors substitution reactions between the zinc reagent and the terminal C–H bond of the alkynes, and prevents the further reactions of the products. Our findings show that iron catalysts can be superior to other metal catalysts in terms of activity, chemoselectivity, regioselectivity, and stereoselectivity when suitable ligands are used.
- Huang, Qiang,Su, Yu-Xuan,Sun, Wei,Hu, Meng-Yang,Wang, Wei-Na,Zhu, Shou-Fei
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supporting information
p. 515 - 526
(2022/01/08)
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- 1,2-Carbopentafluorophenylation of Alkynes: The Metallomimetic Pull-Push Reactivity of Tris(pentafluorophenyl)borane
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We report the novel single-step 1,2-dicarbofunctionalization of an arylacetylene with an allylsilane and tris(pentafluorophenyl)borane [B(C6F5)3] involving C?C bond formation with C?H bond scission at the β-position to the silicon atom of an allylsilane and B→C migration of a C6F5 group. The 1,2-carbopentafluorophenylation occurs smoothly without the requirement for a catalyst or heating. Mechanistic studies suggest that the metallomimetic “pull-push” reactivity of B(C6F5)3 imparts consecutive electrophilic and nucleophilic characteristics to the benzylic carbon of the arylacetylene. Subsequent photochemical 6π-electrocyclization affords tetrafluoronaphthalenes, which are important in the pharmaceutical and materials sciences. Owing to the unique reactivity of B(C6F5)3, the 1,2-carbopentafluorophenylation using 2-substituted furan proceeded with ring opening, and the reaction using silyl enolates formed a C?C bond with C?O bond scission at the silyloxy-substituted carbon.
- Shibuya, Masatoshi,Matsuda, Miki,Yamamoto, Yoshihiko
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supporting information
p. 8822 - 8831
(2021/05/21)
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- Linker Deficiency, Aromatic Ring Fusion, and Electrocatalysis in a Porous Ni8-Pyrazolate Network
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The cruciform linker molecule here features two designer functions: the pyrazole donors for framework construction, and the vicinal alkynyl units for benzannulation to form nanographene units into the Ni8-pyrazolate scaffold. Unlike the full 12 connections of the Ni8(OH)4(H2O)2 clusters in other Ni8-pyrazolate networks, significant linker deficiency was observed here, leaving about half of the Ni(II) sites capped by acetate ligands, which can be potentially removed to open the metal sites for reactivity. The crystalline Ni8-pyrazolate scaffold also retains the crystalline order even after thermal treatments (up to 300 °C) that served to partially graphitize the neighboring alkyne units. The resultant nanographene components enhance the electroactive properties of the porous hosts, achieving hydrogen evolution reaction (HER) activity that rivals that of topical nickel/palladium-enabled materials.
- Hu, Jieying,Deng, Xiangling,Zhang, Hu,Diao, Yingxue,Cheng, Shengxian,Zheng, Sai-Li,Liao, Wei-Ming,He, Jun,Xu, Zhengtao
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p. 161 - 166
(2021/01/11)
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- Invisible Silver Guests Boost Order in a Framework That Cyclizes and Deposits Ag3Sb Nanodots
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The infusion of metal guests into (i.e., metalating) the porous medium of metal-organic frameworks (MOFs) is a topical approach to wide-ranging functionalization purposes. We report the notable interactions of AgSbF6 guests with the designer MOF host ZrL1 [Zr6O4(OH)7(L1)4.5(H2O)4]. (1) The heavy-atom guests of AgSbF6 induce order in the MOF host to allow the movable alkyne side arm to be fully located by X-ray diffraction, but they themselves curiously remain highly disordered and absent in the strucutral model. The enhanced order of the framework can be generally ascribed to interaction of the silver guests with the host alkyne and thioether functions, while the invisible heavy-atom guest represents a new phenomenon in the metalation of open framework materials. (2) The AgSbF6 guests also participate in the thermocyclization of the vicinal alkyne units of the L1 linker (at 450 °C) and form the rare nanoparticle of Ag3Sb supported on the concomitantly formed nanographene network. The resulted composite exhibits high electrical conductivity (1.0 S/cm) as well as useful, mitigated catalytic activity for selectively converting nitroarenes into the industrially important azo compounds, i.e., without overshooting to form the amine side products. The heterogeneous/cyclable catalysis entails only the cheap reducing reagents of NaBH4, ethanol, and water, with yields being generally close to 90%.
- Ahn, Dohyun,Cheng, Shengxian,Feng, Weijin,He, Jun,Hu, Jieying,Xin, Yinger,Xu, Zhengtao,Zeller, Matthias
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supporting information
p. 5757 - 5763
(2021/05/04)
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- Photocatalyzed E→Z Contra-thermodynamic Isomerization of Vinyl Boronates with Binaphthol
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The photocatalytic contra-thermodynamic E→Z isomerization of vinyl boronates by using a binaphthol catalyst is disclosed. The reaction, based on the transient formation of a suitable chromophore with a BINOL derivative as the catalyst, allowed geometrical isomerization in good-to-excellent Z/E ratio and excellent-to-quantitative yields. The mechanism of this E→Z contra-thermodynamic isomerization was studied, and the formation of a transient chromophore species is suggested.
- Brégent, Thibaud,Bouillon, Jean-Philippe,Poisson, Thomas
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supporting information
p. 13966 - 13970
(2021/08/25)
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- Synthesis, Electrochemistry, and Optical Properties of Highly Conjugated Alkynyl-Ferrocenes and -Biferrocenes
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Sonogashira reactions are utilized herein to react iodo-ferrocenes and -biferrocenes with terminal alkyne ligands, functionalized with both pyridine and thioanisole groups. High-yielding reactions generate both monoalkynyl and dialkynyl derivatives, the r
- Bennett, Troy L. R.,Wilkinson, Luke A.,Lok, Jasmine M. A.,O'Toole, Robert C. P.,Long, Nicholas J.
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p. 1156 - 1162
(2021/05/06)
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- Thermal decarboxylative Nazarov cyclization of cyclic enol carbonates involving chirality transfer
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Decarboxylative Nazarov cyclization of chiral cyclic enol carbonates proceeded to afford chiral 2-cyclopentenones with excellent chirality transfer under thermal conditions without any catalyst. Interestingly, the thermal decarboxylative Nazarov cyclization furnished the desired product with better chirality transfer than the Lewis acid-catalyzed reaction.
- Kozuma, Akane,Komatsuki, Keiichi,Saito, Kodai,Yamada, Tohru
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supporting information
p. 60 - 63
(2019/12/12)
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- Synthesis, Structure and Physical Properties of "wire-like" Metal Complexes
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The syntheses and crystallographically determined structures of metal complexes trans-[M(CCR)2Ln] (MLn = Ru(dppe)2, Ru{P(OEt)3}4, Pt(PEt3)2) featuring acetylide ligands further functionalized by aryl thioether groups are reported, together with those of a
- Naher, Masnun,Bock, S?ren,Langtry, Zakary M.,O'Malley, Kieran M.,Sobolev, Alexandre N.,Skelton, Brian W.,Korb, Marcus,Low, Paul J.
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p. 4667 - 4687
(2020/12/22)
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- Symmetrically backfolded molecules emulating the self-similar features of a Sierpinski triangle
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We synthesized self-similar molecules (G3 and G2; based on phenylalkynyl backbones) with symmetrically backfolded shapes inspired by the famous fractal of a Sierpinski triangle. Unlike the more traditional, starburst dendrimers, the centripetal-shaped Sierpinski molecules feature side branches symmetrically bent away from the growth direction of the main branch, thus contrasting the natural-tree shape. Molecule G3 exhibits three distinct levels of the structural hierarchy comprising the primary, secondary and tertiary branches, while the smaller G2 contains only features of the 1st and 2nd orders. In spite of the much larger conjugated backbone of G3, its solution UV-vis absorption and fluorescence exhibit no red shift relative to G2. In a test of nitrobenzene sensing, a thin film of G3 deposited from THF was more sensitively quenched in fluorescence than the smaller G2.
- Hu, Jie-Ying,Sun, Yan-Qiong,Xiao, Ran,Cheng, Shengxian,He, Jun,Zeller, Matthias,Wong, Wai-Yeung,Xu, Zhengtao
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supporting information
p. 6032 - 6037
(2019/06/24)
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- Copper-Mediated Deacylative Coupling of Ynones via C-C Bond Activation under Mild Conditions
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The intermolecular deacylative coupling of unstrained ynones via C-C bond activation was accomplished by a CuCl-bpy system under mild reaction conditions. This protocol features facile cleavage of the C-C bond at room temperature, broad substrate scope, and efficient construction of important symmetric and unsymmetrical 1,3-diyne adducts through homo or cross coupling of ynones, respectively. The preliminary mechanistic investigations indicated that an acyl copper(III) complex is likely involved in this process.
- Feng, Lili,Hu, Tingjun,Zhang, Saisai,Xiong, Heng-Ying,Zhang, Guangwu
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supporting information
p. 9487 - 9492
(2019/12/02)
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- SO2F2-Mediated Oxidative Dehydrogenation and Dehydration of Alcohols to Alkynes
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Direct synthesis of alkynes from inexpensive, abundant alcohols was achieved in high yields (greater than 40 examples, up to 95% yield) through a SO2F2-promoted dehydration and dehydrogenation process. This straightforward transformation of sp3-sp3 (C-C) bonds to sp-sp (C=C) bonds requires only inexpensive and readily available reagents (no transition metals) under mild conditions. The crude alkynes are sufficiently free of impurities to permit direct use in further transformations, as illustrated by regioselective Huisgen alkyne-azide cycloaddition reactions with PhN3 to give 1,4-substituted 1,2,3-traiazoles (16 examples, up to 92% yield) and Sonogashira couplings (10 examples, up to 77% yield).
- Zha, Gao-Feng,Fang, Wan-Yin,Li, You-Gui,Leng, Jing,Chen, Xing,Qin, Hua-Li
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supporting information
p. 17666 - 17673
(2019/01/04)
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- An Additive-Free, Base-Catalyzed Protodesilylation of Organosilanes
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We report an additive-free, base-catalyzed C-, N-, O-, and S-Si bond cleavage of various organosilanes in mild conditions. The novel catalyst system exhibits high efficiency and good functional group compatibility, providing the corresponding products in good to excellent yields with low catalyst loadings. Overall, this transition-metal-free process may offer a convenient and general alternative to current employing excess bases, strong acids, or metal-catalyzed systems for the protodesilylation of organosilanes.
- Yao, Wubing,Li, Rongrong,Jiang, Huajiang,Han, Deman
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p. 2250 - 2255
(2018/02/23)
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- The design of liquid crystalline bistolane-based materials with extremely high birefringence
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We designed three new bistolanes with alkylsulfanyl groups. A symmetric derivative contains short terminal methylsulfanyl groups (-SCH3) on both ends, while two asymmetric derivatives contain a methylsulfanyl group on one end, as well as a highly polarizable cyano (-CN) or isothiocyanate (-NCS) group on the other end. These materials exhibited a well-defined enantiotropic nematic phase, as well as an extremely high birefringence (Δn > 0.6). Most notably, the NCS derivative achieves an extremely high value of 0.77 at 550 nm. These results should be helpful for the design and synthesis of novel nematic materials with high birefringence.
- Arakawa, Yuki,Kang, Sungmin,Tsuji, Hideto,Watanabe, Junji,Konishi, Gen-Ichi
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p. 92845 - 92851
(2016/10/11)
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- Luminescent 1D- and 2D-Coordination Polymers Using CuX Salts (X = Cl, Br, I) and a Metal-Containing Dithioether Ligand
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The organometallic synthon trans-[p-MeSC6H4C≡C-Pt(PMe3)2-C≡CC6H4SMe] (L1) reacts with CuX (X = Cl, Br, I) in PrCN and PhCN to form 1D- or 2D-coordination polymers (CP) with a very high degr
- Juvenal, Frank,Langlois, Adam,Bonnot, Antoine,Fortin, Daniel,Harvey, Pierre D.
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supporting information
p. 11096 - 11109
(2016/11/17)
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- "quick and click" assembly of functionalised indole rings via metal-promoted cyclative tandem reactions
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An efficient and convenient synthesis of a variety of decorated indoles using a three-component tandem metal-catalysed process is described. We propose here a new "synthetic kit" that allows for the "quick and click" assembly of indole rings using readily available, and inexpensive starting materials under environmentally friendly reaction conditions. This journal is
- Capitta, Francesca,De Luca, Lidia,Porcheddu, Andrea
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p. 59297 - 59301
(2015/02/19)
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- The fight against the influenza A virus H1N1: Synthesis, molecular modeling, and biological evaluation of benzofurazan derivatives as viral RNA polymerase inhibitors
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The influenza RNA polymerase complex, which consists of the three subunits PA, PB1, and PB2, is a promising target for the development of new antiviral drugs. A large library of benzofurazan compounds was synthesized and assayed against influenza virus A/WSN/33 (H1N1). Most of the new derivatives were found to act by inhibiting the viral RNA polymerase complex through disruption of the complex formed between subunits PA and PB1. Docking studies were also performed to elucidate the binding mode of benzofurazans within the PB1 binding site in PA and to identify amino acids involved in their mechanism of action. The predicted binding pose is fully consistent with the biological data and lays the foundation for the rational development of more effective PA-PB1 inhibitors. In the fight against influenza virus A/WSN/33 (H1N1), the PA-PB1 protein-protein interaction is emerging as a new drug target. To identify small molecules able to inhibit the viral RNA polymerase complex, the benzofurazan scaffold was explored by synthesizing a large library of derivatives. Some compounds showed high anti-H1N1 activity and emerged as effective inhibitors of the PA-PB1 interaction, with IC50 values in the micromolar range. Copyright
- Pagano, Mafalda,Castagnolo, Daniele,Bernardini, Martina,Fallacara, Anna Lucia,Laurenzana, Ilaria,Deodato, Davide,Kessler, Ulrich,Pilger, Beatrice,Stergiou, Lilli,Strunze, Stephan,Tintori, Cristina,Botta, Maurizio
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p. 129 - 150
(2014/01/17)
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- Pd uptake and H2S sensing by an amphoteric metal-organic framework with a soft core and rigid side arms
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Molecular components of opposite character are often incorporated within a single system, with a rigid core and flexible side arms being a common design choice. Herein, molecule L has been designed and prepared featuring the reverse design, with rigid sid
- Cui, Jieshun,Wong, Yan-Lung,Zeller, Matthias,Hunter, Allen D.,Xu, Zhengtao
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supporting information
p. 14438 - 14442
(2015/02/19)
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- Cross-coupling of nonactivated alkyl halides with alkynyl grignard reagents: A nickel pincer complex as the catalyst
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In a pinch: The nickel pincer complex 1 catalyzes the cross-coupling of the title compounds with remarkable substrate scope and functional group tolerance. A nickel/alkynyl species was isolated and shown to be catalytically competent. THF=tetrahydrofuran, O-TMEDA=bis[2-(N,N-dimethylaminoethyl)] ether. Copyright
- Vechorkin, Oleg,Godinat, Aurélien,Scopelliti, Rosario,Hu, Xile
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supporting information; experimental part
p. 11777 - 11781
(2012/01/19)
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- Synthesis and cyclooxygenase inhibitory activities of linear 1-(methanesulfonylphenyl or benzenesulfonamido)-2-(pyridyl)acetylene regioisomers
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A group of 1-(aminosulfonylphenyl and methylsulfonylphenyl)-2-(pyridyl)acetylene regioisomers were designed such that a COX-2 SO2NH2 pharmacophore was located at the para-position of the phenyl ring, or a SO2Me pharmacopho
- Chowdhury, Morshed Alam,Dong, Ying,Chen, Qiao-Hong,Abdellatif, Khaled R.A.,Knaus, Edward E.
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p. 1948 - 1956
(2008/09/21)
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- Centripetal molecules as multifunctional building blocks for coordination networks
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Centripetally shaped molecules are crystallized with AgSbF6 to yield coordination networks featuring novel coordination modes, network connectivity and chiral/helical structures. The Royal Society of Chemistry.
- Sun, Yan-Qiong,He, Jun,Xu, Zhengtao,Huang, Guo,Zhou, Xiao-Ping,Zeller, Matthias,Hunter, Allen D.
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p. 4779 - 4781
(2008/09/17)
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- Systematic studies on photoluminescence of oligo(arylene-ethynylene)s: Tunability of excited states and derivatization as luminescent labeling probes for proteins
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Functionalized oligo(phenylene-ethynylene)s (OPEs) with different conjugation lengths, p-X(C6H4C≡C) nSiMe3 (n = 1-4; X = NH2, NMe2, H) were synthesized by Sonogashira coupling of (phenylene-ethynylene)s and 1-iodo-4-(trimethylsilylethynyl)benzene, followed by desilylation of the p-substituted (trimethylsilylethynyl)benzenes with potassium hydroxide. The photoluminescent properties for the OPE series with different chain lengths and their solvatochromic responses were examined. The absorption maxima were red-shifted with increasing numbers of -(C6H4C≡C)- units (n), and a linear plot of the absorption energy maxima vs. 1/n was obtained for each series. The emission spectra in dichloromethane showed a broad and structureless band, the energies of which (in wavenumbers) also fit linearly with 1/n. Both the absorption and emission wavelength maxima of the NH2- and NMe2-substituted OPEs exhibited significant solvent dependence, whereas the parent OPEs (X = H) showed only minor shifts of the λmax values in different solvents. Substituent effects upon the photoluminescent characteristics of the OPEs and the tunability of the excited states were examined with the p-X(C6H4C≡C) nSiMe3 (n = 2, 3; X = NH2, NMe2, H, SMe, OMe, OH, and F) series. The H- and F-substituted counterparts exhibited high-energy vibronically structured emissions attributed to the 3(ππ*) excited states of the (arylene-ethynylene) backbone. For compounds bearing NH2 and NMe2 groups, a broad red-shifted emission with a remarkable Stokes shift from the respective absorption maximum was observed, which can be assigned to an n → π* transition. The n → π* assignment was supported by MO calculations on the model compounds p-X(C6H4C≡C) 2SiH3 (X = NH2, H). Functionalization of the oligo(arylene-ethynylene)s with the N-hydroxysuccinimidyl (NHS) moiety enabled covalent attachment of the fluorophore to HSA protein molecules. A series of fluorescent labels, namely p-X(C6H4C≡C) n-C6H4NHS, (n = 1, X = NH2, NMe 2, SMe, OMe, OH, F; n = 2, X = NH2, NMe2) and p-Me2NC6H4C≡C(C4H 2S)-C≡CC6H4NHS were synthesized, and their conjugates with HSA (human serum albumin) were characterized by MALDI-TOF mass spectrometry, UV/Vis absorption spectroscopy, and gel electrophoresis. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Zhi, Yong-Gang,Lai, Siu-Wai,Chan, Queenie K.-W.,Law, Yuen-Chi,Tong, Glenna S.-M.,Che, Chi-Ming
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p. 3125 - 3139
(2007/10/03)
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- New fluorophores with rod-shaped polycyano π-conjugated structures: Synthesis and photophysical properties
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Novel rod-shaped polycyano-oligo(phenyleneethynylene)s were synthesized by Pd cross-coupling reaction. Polycyano groups were found to greatly improve the emission efficiency (Φf) of OPEs. By the end donor modification, we achieved the creation of very intense blue light-emitting fluorophore with the SMe group (Φf) = 0.972, log ε 4.89, λ em 455 nm) and very intense yellow light-emitting fluorophore with the NMe2 group (Φf = 0.999, log ε 4.75, λem 555 nm). Contrasting Φf solvent dependency of 6 and 7 and a linear relationship between Φf and σp-X over the whole region of σp-X were also found.
- Yamaguchi, Yoshihiro,Ochi, Takanori,Wakamiya, Tateaki,Matsubara, Yoshio,Yoshida, Zen-Ichi
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p. 717 - 720
(2007/10/03)
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- Synthesis and structure-activity relationship studies of 1,3-diarylprop-2-yn-1-ones: Dual inhibitors of cyclooxygenases and lipoxygenases
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A group of 1,3-diarylprop-2-yn-1-ones (13, 17, 23, 26 and 27) possessing a C-3 p-SO2Me COX-2 pharmacophore were designed, synthesized and evaluated as potential dual inhibitors of cyclooxygenase-1/2 (COX-1/2) and 5/15-lipoxygenases (5/15-LOX) t
- Rao, P. N. Praveen,Chen, Qiao-Hong,Knaus, Edward E.
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p. 1668 - 1683
(2007/10/03)
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- Synthesis and biological evaluation of 1,3-diphenylprop-2-yn-1-ones as dual inhibitors of cyclooxygenases and lipoxygenases
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A new class of 1,3-diphenylprop-2-yn-1-ones possessing a p-MeSO2 COX-2 phamacophore on the C-3 phenyl ring was designed for evaluation as dual inhibitors of cyclooxygenase (COX) and lipoxygenase (LOX). Among the group of compounds evaluated, 1-
- Rao, P.N. Praveen,Chen, Qiao-Hong,Knaus, Edward E.
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p. 4842 - 4845
(2007/10/03)
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- Highly regiocontrolled pd-catalyzed cross-coupling reaction of terminal alkynes and allenylphosphine oxides
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The cross-coupling of a variety of terminal alkynes 1 with allenylphosphine oxides 2 catalyzed by a Pd(OAc)2-TDMPP system provided conjugated endo-enynes 3 solely, while the TCPC-catalyzed reaction of the same regents led to the exclusive forma
- Rubin, Michael,Markov, Jelena,Chuprakov, Stepan,Wink, Donald J.,Gevorgyan, Vladimir
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p. 6251 - 6256
(2007/10/03)
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- Synthesis and preliminary testing of molecular wires and devices
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Presented here are several convergent synthetic routes to conjugated oligo(phenylene ethynylene)s. Some of these oligomers are free of functional groups, while others possess donor groups, acceptor groups, porphyrin interiors, and other heterocyclic interiors for various potential transmission and digital device applications. The syntheses of oligo(phenylene ethynylene)s with a variety of end groups for attachment to numerous metal probes and surfaces are presented. Some of the functionalized molecular systems showed linear, wire-like, current versus voltage (I(V)) responses, while others exhibited nonlinear I(V) curves for negative differential resistance (NDR) and molecular random access memory effects. Finally, the syntheses of functionalized oligomers are described that can form self-assembled monolayers on metallic electrodes that reduce the Schottky barriers. Information from the Schottky barrier studies can provide useful insight into molecular alligator clip optimizations for molecuar electronics.
- Tour, James M.,Rawlett, Adam M.,Kozaki, Masatoshi,Yao, Yuxing,Jagessar, Raymond C.,Dirk, Shawn M.,Price, David W.,Reed, Mark A.,Zhou, Chong-Wu,Chen, Jia,Wang, Wenyong,Campbell, Ian
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p. 5118 - 5134
(2007/10/03)
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- Ethynylation of aryl halides by a modified Suzuki reaction: Application to the syntheses of combretastatin A-4, A-5 and lunularic acid
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On treatment with trimethyl borate sodium acetylide undergoes a palladium-catalyzed cross coupling with functionalized aryl halides or triflates in reasonable to good yields. The ethynylarenes thus obtained serve as building blocks for the formation of the highly effective tubulin polymerization inhibitors combretastatin A-4 (1) and A-5 (2) as well as for the synthesis of the plant-growth regulator lunularic acid (36). VCH Verlagsgesellschaft mbH, 1996.
- Fuerstner, Alois,Nikolakis, Katharina
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p. 2107 - 2113
(2007/10/03)
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- The electronic structure and second-order nonlinear optical properties of donor-acceptor acetylenes: A detailed investigation of structure-property relationships
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A series of donor-acceptor acetylene compounds was synthesized in which systematic in both the conjugation length and the donor-acceptor strength were made. The effect of these structural changes on the spectrcscopic electronic proprties of the molecules
- Stiegman,Graham, Eva,Perry, Kelly J.,Khundkar, Lutfur R.,Cheng,Perry, Joseph W.
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p. 7658 - 7666
(2007/10/02)
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