145483-64-3Relevant articles and documents
Click functionalization of a dibenzocyclooctyne-containing conjugated polyimine
Kardelis, Vladimir,Chadwick, Ryan C.,Adronov, Alex
, p. 945 - 949 (2016/01/20)
A conjugated poly(phenyl-co-dibenzocyclooctyne) Schiff-base polymer, prepared through polycondensation of dibenzocyclooctyne bisamine (DIBO-(NH2)2) with bis(hexadecyloxy)phenyldialdehyde, is reported. The resulting polymer, which has
Molecular spoked wheels: Synthesis and self-assembly studies on rigid nanoscale 2D objects
Aggarwal, A. Vikas,Jester, Stefan-S.,Taheri, Sara Mehdizadeh,Foerster, Stephan,Hoeger, Sigurd
, p. 4480 - 4495 (2013/05/23)
We present the efficient synthesis of a new molecular spoked-wheel structure (MSW-3). Two derivatives with diameters of approximately 4 nm have been prepared. By highlighting the importance of pseudo-high-dilution conditions during cyclization, we were able to access the compounds on a several hundred milligram scale. In addition to the standard characterization (NMR spectroscopy, MS), we describe a detailed investigation of the optical properties of the fluorescent MSWs by comparison with appropriate model chromophores. Furthermore, a comprehensive study of the structure in solution by means of light- and X-ray scattering experiments has been conducted. Scanning tunneling microscopy (STM) revealed the two-dimensional organization of the molecules on highly oriented pyrolytic graphite and emphasized the spoked-wheel structure. The diameter of these molecules measured by small-angle X-ray scattering is in very good agreement with that obtained from STM and matches the results of molecular modeling. This confirms the rigidifying effect of the spokes, which results in highly shape-persistent nanometer-sized oblate organic compounds. Copyright
Two-dimensional oligo(phenylene-ethynylene-butadiynylene)s: All-covalent nanoscale spoked wheels
Lei, Shengbin,Heyen, An Ver,De Feyter, Steven,Surin, Mathieu,Lazzaroni, Roberto,Rosenfeldt, Sabine,Ballauff, Matthias,Lindner, Peter,Moessinger, Dennis,Hoeger, Sigurd
supporting information; experimental part, p. 2518 - 2535 (2009/11/30)
The synthesis and characterization of a shape-persistent two-dimensional (2D) organic compound is described in detail. In a rational modular synthesis of a dodecaacetylene precursor and its subsequent template-aided cyclization, we obtained a molecularly defined, stable, C6-symmetric, rigid, spoked wheel. Peripheral tert-butyl groups and alkyl chains attached to the plane of the molecule provide sufficient solubility, so that the 2D oligomer can be fully characterized by MALDINIS, GPC, and 1HNMR, UV/Vis absorption, and fluorescence spectroscopy. Molecular mechanics and dynamics simulations indicate that the most stable conformer of the molecule in vacuum is a shallow boat conformation with a small dihedral angle. Comparisons with the precursor as well as a ring-only structure clearly reveal the high rigidity of the title compound. Small-angle neutron scattering (SANS) experiments in [D 8]THF and CDCl3 affirm the rigid backbone structure in solution, that is, a radius of about 2.7 nm and a thickness of about 0.22 nm. STM investigations illustrate that the wheel molecules adsorb with their molecular plane parallel to the surface and can form hexagonal crystalline domains (unit cell parameters are a = b = 6.0±0.2 nm and θ=60±2°), with the iert-butyl groups on the apexes staggered. Such staggering induces chirality in the organized domains. AFM investigations demonstrate that the wheel molecules inside overlayers organize in the same way as in the layer directly in contact with the surface. This indicates an epitaxial growth characteristic of the film.
Design principles to tune the optical properties of 1,3,4-oxadiazole- containing molecules
Bolton, Onas,Kim, Jinsang
, p. 1981 - 1988 (2008/02/08)
We have synthesized a series of oxadiazole compounds and ethynylene analogs. Our data reveal that the ring is both optically transparent in the visible range and fully conjugating while we have also discovered the presence of a non-radiative mechanism active in molecules containing common para-dialkoxy substituents adjacent to the oxadiazole ring(s). This structure leads to a greatly reduced quantum yield, in our example dropping from 95.0% to 48.0%. Through our thorough study we have revealed evidence that this is the result of a repulsive interaction between the oxadiazole and the adjacent alkoxy oxygen atom, which we believe prevents excited-state planarity. This quantum yield reduction is preventable through the design principles presented here. The Royal Society of Chemistry 2007.
Efficient synthesis of 1,4-dialkoxy and 1,4-dialkyl substituted 2,5-divinylbenzenes via the Stille reaction
Daoud, Walid A.,Turner, Michael L.
, p. 367 - 369 (2007/10/03)
An efficient palladium catalyzed cross coupling of tributyl(vinyl)stannane with dialkoxy and dialkyl substituted 1,4-dihalobenzenes is described. This single-step coupling provides an efficient synthesis of functionalized 2,5-divinylbenzenes, which are us
TRANSITION-METAL CHARGE-TRANSPORT MATERIALS, METHODS OF FABRICATION THEREOF, AND METHODS OF USE THEREOF
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Sheet 60, (2010/02/15)
Briefly described, embodiments of this disclosure include transition-metal charge-transport materials, methods of forming transition-metal charge-transport materials, and methods of using the transition-metal charge-transport materials.
The CA.M lattice revisited. Gel formation from a linear bis-isocyanuric acid and 2-amino-4,6-bis-(4-tert-butylphenylamino)-1,3,5-triazine
Plater, M. John,Sinclair, James P.,Aiken, Stuart,Gelbrich, Thomas,Hursthouse, Michael B.
, p. 6385 - 6394 (2007/10/03)
Five bis(isocyanuric) acid dimers have been prepared and characterised. The introduction of flexible alkyl chains was necessary to aid solubility. On mixing with N,N-bis(4-tert-butyphenyl)melamine in THF followed by slow evaporation, a viscous gel can form which is interpreted as evidence for the assembly of an infinite 2-D hydrogen bonded network.
Fluorescence Studies of Poly(p-phenyleneethynylene)s: The Effect of Anthracene Substitution
Swager, Timothy M.,Gil, Caroline J.,Wrighton, Mark S.
, p. 4886 - 4893 (2007/10/02)
The poly(p-phenyleneethynylene) molecules, PI-PIII, synthesized by a palladium-catalyzed cross-coupling reaction of diiodobenzene derivatives and derivatives of 1,4-diethynylbenzene, are highly luminescent materials.The polymers are soluble by virtue of the -OC16H33 groups introduced on the aromatic rings and by controlling their molecular weight.The fluorescent quantum yields are between 0.35 and 0.40 depending on the material.The excited-state lifetimes of the polymers are 1-2 ns, slightly shorter than that of the model compund, 1,4-diphenylethynyl-2,5-dibutoxybenzene, which has a lifetime of 3 ns.Incorporation of anthracene, coupled at the 9,10-positions by using 9,10-dibromoanthracene, into the polymer backbone decreases the quantum yield to between 0.05 and 0.27 depending on the anthracene content.In addition, low-energy electronic transitions and longer wavelength emission bands associated with the anthracene group are produced.The polymers harvest optical energy and transfer it to the anthracene resulting in emission from this chromophore.In the case where only terminal anthracene units, introduced by using 9-bromo-10-phenylethynylanthracene, are present, the process is very efficient with >95percent of the energy being transferred to the end groups.
