81216-13-9Relevant articles and documents
Synthesis of a pH-Sensitive Hetero[4]Rotaxane Molecular Machine that Combines [c2]Daisy and [2]Rotaxane Arrangements
Waelès, Philip,Riss-Yaw, Benjamin,Coutrot, Frédéric
, p. 6837 - 6845 (2016)
The synthesis of a novel pH-sensitive hetero[4]rotaxane molecular machine through a self-sorting strategy is reported. The original tetra-interlocked molecular architecture combines a [c2]daisy chain scaffold linked to two [2]rotaxane units. Actuation of the system through pH variation is possible thanks to the specific interactions of the dibenzo-24-crown-8 (DB24C8) macrocycles for ammonium, anilinium, and triazolium molecular stations. Selective deprotonation of the anilinium moieties triggers shuttling of the unsubstituted DB24C8 along the [2]rotaxane units.
Alkyne metatheses in transition metal coordination spheres: Convenient tungsten- and molybdenum-catalyzed syntheses of novel metallamacrocycles
Bauer, Eike B.,Hampel, Frank,Gladysz
, p. 812 - 822 (2004)
Reactions of (CO)5Re(Br), (η5-C5H 5) Ru(Cl)(PPh3)2, and [Pt(μ-Cl)(C 6F5)(S(CH2CH2-)2)] 2 with the alkyne-containing phosphi
Nucleic acid base analogs with quenching and fluorescent activities and applications thereof
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Paragraph 47, (2016/04/05)
It is an object of the present invention to provide quenching or fluorescent nucleic acid base analogs and applications thereof. The quencher of the present invention has a 2-nitropyrrole structure represented by Formula I: [Formula 1] (in Formula I, Rsu
Very contracted to extended co -conformations with or without oscillations in two- and three-station ['2]daisy chains
Romuald, Camille,Busseron, Eric,Coutrot, Frederic
supporting information; experimental part, p. 6516 - 6531 (2010/12/24)
The syntheses of various two- and three-station mannosyl [c2]daisy chains, based on a dibenzo-24-crown-8 macrocyclic moiety and an ammonium, a triazolium, and a mono- or disubstituted pyridinium amide station, are reported. The ability of these molecules to act as molecular machine based mimetics has been further studied by 1H NMR studies. In all the protonated ammonium states, the interwoven rotaxane dimers adopt an extended co-conformation. However, carbamoylation of the ammonium station led to many different other [c2]daisy chain co-conformations, depending on the other molecular stations belonging to the axle. In the two-station [c2]daisy chains containing an ammonium and a mono- or disubstituted pyridinium amide station, two large-amplitude relative movements of the interwoven components were noticed and afforded either an extended and a contracted or very contracted state with, in the latter case, an impressive chairlike conformational flipping of the mannopyranose from 1C4 to 4C1. In the case of the three-station-based [c2]daisy chains containing an ammonium, a triazolium, and disubstituted pyridinium amide, an extended and a half-contracted molecular state could be obtained because of the stronger affinity of the dibenzo-24-crown-8 part for, respectively, the ammonium, the triazolium, and the disubstituted pyridinium amide. Eventually, with axles comprising an ammonium, a triazolium, and a monosubstituted pyridinium amide, an extended conformation was noticed in the protonated state whereas a continuous oscillation between half-contracted and contracted states, in fast-exchange on the NMR time scale, was triggered by carbamoylation. Variations of the solvent or the temperature allow the modification of the population of each co-conformer. Thermodynamic data provided a small free Gibbs energy δG of 2.1 kJ·mol -1 between the two translational isomers at 298 K.
Effects of substitution and terminal groups for liquid-crystallinity enhanced luminescence of disubstituted polyacetylenes carrying chromophoric terphenyl pendants
Zhou, Dan,Chen, Yiwang,Chen, Lie,Li, Fan,Nie, Huarong,Yao, Kai
experimental part, p. 1302 - 1315 (2010/11/05)
Liquid-crystalline and light-emitting poly(2-alkyne)s containing terphenyl cores with hexamethyleneoxy spacers, and cyano or n-propoxy tails - [CH3C=C(CH2)6O-terphenyl-R] n -, where R=CN, CH3PA6CN, R=OCH2CH 2CH3, CH3PA6OPr, were synthesized. The effects of the substitution and terminal groups on the properties, especially the mesomorphic and optical properties of the polymers, were investigated. The disubstituted acetylene monomers (CH3A6CN, CH3A6OPr) were prepared through multistep reaction routes and were polymerized by WCl6-Ph4Sn in good yields (up to 82%). All the monomers and CH3PA6CN exhibited the enantiotropic SmA phase with a monolayer arrangement at elevated temperatures, whereas CH3PA6OPr formed a bilayer SmAd packing arrangement. Upon excitation at 330 nm, strong UV and blue emission peaks at 362 and 411 nm were observed in CH3PA6OPr and CH3PA6CN, respectively. The luminescent properties of CH3PA6CN and CH3PA6OPr have been improved by introducing the methyl substituted group, and the quantum yield of the polymer with cyano tail CH3PA6CN (Φ = 74%) was found to be higher than that of CH3PA6OPr (Φ = 60%). Compared to polyacetylene parents, both CH3PA6OPr and CH3PA6CN showed a narrower energy gap. This demonstrated that the electrical conductivities of polyacetylenes could be enhanced by attaching appropriate pendants to the conjugated polyene backbones.
6,6′-Dimethyl-2,2′-bipyridine-4-ester: A pivotal synthon for building tethered bipyridine ligands
Havas, Fabien,Leygue, Nadine,Danel, Mathieu,Mestre, Béatrice,Galaup, Chantal,Picard, Claude
experimental part, p. 7673 - 7686 (2009/12/06)
We describe an efficient and scalable synthesis of 4-carbomethoxy-6,6′-dimethyl-2,2′-bipyridine starting from easily available substituted 2-halopyridines and based on the application of modified Negishi cross-coupling conditions. This compound is a versatile starting material for the synthesis of 4-functionalized 2,2′-bipyridines bearing halide, alcohol, amine, and other functionalities, suitable for conjugation to biological material (2a-c, 3a-g). The utility of this compound in the construction of more complex architectures was further demonstrated by the synthesis of two bifunctional lanthanide chelators; an open chain ligand based on one 2,2′-bipyridine unit and a cryptand based on three 2,2′-bipyridine units [N2(bpy)3COOMe]. In the field of luminophoric biolabels, the photophysical properties of the corresponding Eu(III) cryptate are reported.
A new pH-switchable dimannosyl[c2]daisy chain molecular machine
Coutrot, Frederic,Romuald, Camille,Busseron, Eric
supporting information; experimental part, p. 3741 - 3744 (2009/07/09)
(Figure Presented) The preparation of a dimannosyl[c2]daisy chain molecular machine containing an ammonium and a triazolium station is described. The both stretched and contracted states of the molecular machine can be obtained by variation of the pH, thus localizing the mannosyl stoppers closer or farther away.
Synthesis and properties of polymers from monosubstituted acetylene derivatives bearing ferroelectric liquid crystalline groups
Goto, Hiromasa,Dai, Xiaoman,Ueoka, Takenori,Akagi, Kazuo
, p. 4783 - 4793 (2007/10/03)
Novel liquid crystalline polyacetylene derivatives were developed as advanced LC conjugated polymers with quick response to an electric field used as external force. In practice, we synthesized ferroelectric LC conjugated polymers by introducing fluorine-
Efficient synthesis of 40- and 48-membered tetraether macrocyclic bisphosphocholines.
Patwardhan,Thompson
, p. 241 - 243 (2008/02/13)
An efficient route toward the synthesis of unsaturated (bis-diacetylenic) and saturated 40- and 48-membered macrocyclic biphosphocholines has been developed using 2-phenyl-5-hydroxy-1,3-dioxane as a common glycerol synthon. Ring closure was accomplished using either high-dilution Glaser oxidation of [(Cy3P)2RU==CHPh]Cl2-catalyzed olefin metathesis conditions. Deprotection of benzyl ethers using trimethylsilyl iodide (TMS-I) in the presence of diacetylenic moieties has also been demonstrated for the first time.
Synthesis of Saturated Anacardic Acids, and Alkenyl and Alkynyl Analogues
Tyman, John H. P.,Visani, Naina
, p. 228 - 240 (2007/10/03)
The C-alkylation of esters of 2-methoxy-6-methylbenzoic acid and of the 4-methyl isomers affords a route to homologous compounds including in the former case members of the natural anacardic acids from Anacardium occidentale and ω-alkynyl compounds suitable for synthesising other natural phenolic lipids or for structure/activity studies.
