67973-34-6Relevant academic research and scientific papers
4-iodophenyl substituted carborane derivative and preparation method thereof
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, (2020/12/30)
The invention discloses a 4-iodophenyl carborane derivative and a preparation method thereof. Commercialized organic reagents 4-iodoaniline and a diacetonitrile decaborate complex and several easily-synthesized substituted alkynes are adopted as the start
Programmed twisting of phenylene-ethynylene linkages from aromatic stacking interactions
Mullin, William J.,Pawle, Robert H.,Sharber, Seth A.,Müller, Peter,Thomas, Samuel W.
, p. 1198 - 1207 (2019/02/07)
Control over the conformation and packing of conjugated materials is an unsolved problem that prevents the rational design of organic optoelectronics, such as preventing self-quenching of luminescent molecules. Exacerbating this challenge is a general lack of widely applicable strategies for controlling packing with discrete, directional non-covalent interactions. Here, we present a series of conjugated molecules with diverse backbones of three or four arenes that feature pentafluorobenzyl ester substituents. Nearly all the compounds reveal intramolecular stacking interactions between the fluoroarene (ArF) side-chains and non-fluorinated arenes (ArH) in the middle of the chromophores; a twisted PE linkage accompanies each example of this intramolecular ArF-ArH stacking. Furthermore, these molecules can resist dramatic changes to emission upon transition from organic solution to thin film when ArF rings prevent interchromophore interactions. By broadening the structural space of conjugated backbones over which ArF-ArH stacking can twist PE linkages reliably and prevent self-quenching of solids with simple synthetic approaches, this work suggests fluorinated benzyl ester substituents adjacent to phenylene ethynylene linkages as supramolecular synthons for the crystal engineering of organic optoelectronic materials.
How Large Can We Build a Cyclic Assembly? Impact of Ring Size on Chelate Cooperativity in Noncovalent Macrocyclizations
Montoro-García, Carlos,Mayoral, María J.,Chamorro, Raquel,González-Rodríguez, David
, p. 15649 - 15653 (2017/12/02)
Self-assembled systems rely on intramolecular cooperative effects to control their growth and regulate their shape, thus yielding discrete, well-defined structures. However, as the size of the system increases, cooperative effects tend to dissipate. We analyze here this situation by studying a set of oligomers of different lengths capped with guanosine and cytidine nucleosides, which associate in cyclic tetramers by complementary Watson–Crick H-bonding interactions. As the monomer length increases, and thus the number of C(sp)–C(sp2) σ-bonds in the π-conjugated skeleton, the macrocycle stability decreases due to a notable reduction in effective molarity (EM), which has a clear entropic origin. We determined the relationship between EM or ΔS and the number of σ-bonds, which allowed us to predict the maximum monomer lengths at which cyclic species would still assemble quantitatively, or whether the cyclic species would not able to compete at all with linear oligomers over the whole concentration range.
Double elimination protocol for convenient synthesis of dihalodiphenylacetylenes: Versatile building blocks for tailor-made phenylene-ethynylenes
Orita, Akihiro,Miyamoto, Kazuhiko,Nakashima, Mikio,Ye, Fangguo,Otera, Junzo
, p. 767 - 776 (2007/10/03)
Dihalodiphenylacetylenes are conveniently synthesized by a double elimination reaction of β-substituted sulfones which are readily obtained from halogen-substituted benzyl sulfone and benzaldehyde derivatives. Halogens can be incorporated at any desired positions in the diphenylacetylene skeleton simply by choosing the substitution position of the halogen on the aromatic rings of the starting compounds. The diphenylacetylenes with different halogen substituents thus obtained undergo sequential carbon-carbon bond formations due to the different reactivities of the halogens. Thus, various moieties can be incorporated on the diphenylacetylene skeleton at whichever positions so that a variety of tailor-made phenylene-ethynylenes with regulated structure and composition could be designed.
Big macrocyclic assemblies of carboranes (big MACs): Synthesis and crystal structure of a macrocyclic assembly of four carboranes containing alternate ortho- and meta-carborane icosahedra linked by para-phenylene units
Fox, Mark A.,Howard, Judith A.K.,Hugh MacBride,Mackinnon, Angus,Wade, Kenneth
, p. 155 - 164 (2007/10/03)
The macrocyclic compound, [1,2-C2B10 H10-1,4-C6H4-1,7-C2 B10H10-1,4-C6H4] 2 (5)-a novel cyclooctaphane, was prepared by condensation o
Synthesis of nanostructures based on 1,4- and 1,3,5-ethynylphenyl subunits with π-extended conjugation. Carbon dendron units
Gonzalo Rodriguez,Esquivias, Jorge,Lafuente, Antonio,Diaz, Cristina
, p. 8120 - 8128 (2007/10/03)
Nanometer-sized conjugated 1,4- and 1,3,5-ethynylphenyl oligomers were synthesized starting from 3,5-di(trimethylsilylethynyl)phenylacetylene and p-[3,5-di(trimethylsilylethynyl)-1-ethynylphenyl]-phenyl acetylene by cross-coupling reaction with a convenient haloaryl derivative, catalyzed by palladium(II)/copper(I), in excellent yield. The terminal acetylenes were efficiently prepared by a specific protection-deprotection methodology. All ethynylphenyl homologues obtained show fluorescence emission, with the bathochromic shift of approximately 20 nm by each ethynylphenyl unit increasing the conjugate chain. Parallel conjugated ethynylphenyl chains were prepared through the insertion of a 1,5-naphthalene subunit, and the compounds exhibit fluorescence radiation emission.
Synthesis of nanostructures based on 1,4- and 1,3,5-phenylethynyl units with π-extended conjugation. Carbon networks dendrimer base units
Rodríguez, J. Gonzalo,Esquivias
, p. 4831 - 4834 (2007/10/03)
A convenient and efficient synthesis of 3,5-di(silylethynyl)phenylacetylene and p-[3,5-di(silylethynyl)phenylethynyl]phenylacetylene has been carried out. These compounds serve to prepare nanometer-sized conjugated 1,4- and 1,3,5-phenylethynyl oligomers,
Synthesis of nanometer-sized homo- and heteroorganometallic tripodaphyrins
Mongin, Olivier,Gossauer, Albert
, p. 6835 - 6846 (2007/10/03)
Tripodaphyrins are tetrahedral or pyramidal assemblies in which a porphyrin macrocycle situated on the top of the molecule is 'supported' by three 'legs' consisting of linear arrays of covalently linked rigid constitutive elements. The edge-length at the 'base' of the molecules which have been synthesized until now lies in the range from 3.2 to 6.5 nm. In some tripodaphyrins (3a-c) the chromophore situated on the top of the molecule differs on the complexed metal ion from the other three, which are located at the ends of the 'legs'. Owing to the dimensions of the molecules, no intramolecular interaction between the chronophores is observed, even in the presence of a paramagnetic Cu(II) chelate.
