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α‐Halogenoacetanilides as Hydrogen‐Bonding Organocatalysts that Activate Carbonyl Bonds: Fluorine versus Chlorine and Bromine 下载免费PDF全文
Dr. Sylvain Koeller Dr. Coralie Thomas Dr. Fréderic Peruch Dr. Alain Deffieux Dr. Stéphane Massip Prof. Dr. Jean‐Michel Léger Dr. Jean‐Pierre Desvergne Prof. Dr. Anne Milet Dr. Brigitte Bibal 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(10):2849-2859
α‐Halogenoacetanilides (X=F, Cl, Br) were examined as H‐bonding organocatalysts designed for the double activation of C?O bonds through NH and CH donor groups. Depending on the halide substituents, the double H‐bond involved a nonconventional C?H???O interaction with either a H?CXn (n=1–2, X=Cl, Br) or a H?CAr bond (X=F), as shown in the solid‐state crystal structures and by molecular modeling. In addition, the catalytic properties of α‐halogenoacetanilides were evaluated in the ring‐opening polymerization of lactide, in the presence of a tertiary amine as cocatalyst. The α‐dichloro‐ and α‐dibromoacetanilides containing electron‐deficient aromatic groups afforded the most attractive double H‐bonding properties towards C?O bonds, with a N?H???O???H?CX2 interaction. 相似文献
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McSkimming G Tucker JH Bouas-Laurent H Desvergne JP Coles SJ Hursthouse MB Light ME 《Chemistry (Weinheim an der Bergstrasse, Germany)》2002,8(15):3331-3342
Aza-crown ethers 2 and 3 with anthracene-containing pendant arms have been synthesised and characterised. Both compounds bind Group 1 metal cations in solution, forming complexes of 1:1 stoichiometry. The properties of compound 2 and its complexes have been studied by a range of techniques, including NMR, UV and fluorescence spectroscopy and X-ray crystallography. The pendant arms can adopt either a cis or a trans geometry, the cis geometry favoured with larger cations. The geometry of the complex affects the fluorescence properties of the system, with larger cations giving higher excimer/monomer ratios. Upon irradiation at lambda>300 nm, coronand 2 forms the cryptand 5 through a reversible intramolecular [4pi+4pi] cycloaddition reaction. The rates of the forward and reverse reactions of this photochromic process are cation dependent; in particular the rate of the thermal reverse reaction is decreased by smaller cations and increased by larger cations, especially Rb(+). The metal binding constants in methanol for 2 and 5 have been determined, revealing that the cryptand 5 binds Na(+) and Rb(+) more weakly than crown ether 2 by over two orders of magnitude. 相似文献
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[structure: see text] A new type of donor-spacer-acceptor podand system has been synthesized and proved as an efficient dual channel fluorosensor for Li+, Mg2+, and Ca2+. The known ability for the N-oxide function to bind Lewis acids is the key step in the appearance of a new emitting charge-transfer (CT) excited state. The occurrence of this CT state for alkaline earth (Mg2+ and Ca2+) and not for alkaline metals (Li+) provided a new type of dual channel fluorosensors. 相似文献
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Jean-Pierre Desvergne Alain Castellan Henri Bouas-Laurent 《Tetrahedron letters》1981,22(36):3529-3532
New dissymetrical non conjugated bichromophores linked by an oxygenated chain: (9-anthrylmethyloxymethyl)arenes[arenes:benzene(Ia),2-naphthalene(Ib),9-phenanthrene (Ic) and 1-pyrene (Id) and (9-phenanthrylmethyloxymethyl)-1-pyrene (II)] have been prepared. Ic–d and II exhibit intramolecular exciplex fluorescence in methylcyclohexane at room temperature. Intramolecular photoadducts were not found but Ia–d yield a mixture of head-to-head and head-to-tail anthracenic photodimers. 相似文献
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Alkynyl ruthenium colorimetric sensors: optimizing the selectivity toward fluoride anion 总被引:1,自引:0,他引:1
Fillaut JL Andriès J Perruchon J Desvergne JP Toupet L Fadel L Zouchoune B Saillard JY 《Inorganic chemistry》2007,46(15):5922-5932
We report on the synthesis of alkynyl ruthenium colorimetric sensors whose receptors are constituted by thiazolidinedione, rhodanine, or barbituric heads as recognition centers for anions. As modifications in the charge density at these recognition centers affect the whole molecule, through the alkynyl ligand acting as a communicating wire, the effects of hydrogen-bonding interactions with the anions were observed with the naked eye and monitored by UV-vis absorption spectrometry. The selectivity of the sensors was improved through electronic modifications of the alkynyl ruthenium subunit: the higher the electron density at the receptor head, the higher the selectivity is. TD-DFT calculations rationalize the long-range electronic communication as a main characteristic of the alkynyl ruthenium species and as a key to improve the selectivity of alkynyl ruthenium-based sensors toward anions. 相似文献
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Magnetic alignment of self-assembled anthracene organogel fibers 总被引:1,自引:0,他引:1
Shklyarevskiy IO Jonkheijm P Christianen PC Schenning AP Del Guerzo A Desvergne JP Meijer EW Maan JC 《Langmuir : the ACS journal of surfaces and colloids》2005,21(6):2108-2112
High magnetic fields are shown to be remarkably effective to orient self-assembled 2,3-bis-n-decyloxyanthracene (DDOA) fibers during organogel preparation. Magnetic orientation of DDOA results in a highly organized material displaying a fiber-orientation order parameter of 0.85, a large linear birefringence, and fluorescence dichroism. The aligned organogel is stable after removal of the magnetic field at room temperature and consists of fibers oriented perpendicular to the magnetic field direction, as shown by scanning electron microscopy. Models for the molecular organization within the gel fibers are discussed upon quantitative analysis of the birefringence. Prospectively, magnetic alignment can be used to improve specific properties of organogel materials. 相似文献
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