Author: Norberto Farfán

Synthesis and fluorescence emission of neutral and anionic di- and tetra-carboranyl compounds

2011

A new family of photoluminescent neutral and anionic di-carboranyl and tetra-carboranyl derivatives have been synthesized and characterized. The reaction of α,α'-bis(3,5-bis(bromomethyl)phenoxy-m-xylene with 4 equiv. of the monolithium salt of 1-Ph-1,2-C(2)B(10)H(11) or 1-Me-1,2-C(2)B(10)H(11) gives the neutral tetracarboranyl-functionalized aryl ether derivatives closo-1 and closo-2, respectively. The addition of the monolithium salt of 1-Ph-1,2-closo-C(2)B(10)H(11) to α,α,'-dibromo-m-xylene or 2,6-dibromomethyl-pyridine gives the corresponding di-carboranyl derivatives closo-3 and closo-4. These compounds, which contain four or two closo clusters, were degraded using the classical method,…

Boron CompoundsModels MolecularMagnetic Resonance SpectroscopySubstituentSalt (chemistry)Ether010402 general chemistryPhotochemistryCrystallography X-Ray01 natural sciencesInorganic Chemistrychemistry.chemical_compoundPolymer chemistryPyridineMoleculeta116Tetramethylammoniumchemistry.chemical_classificationLuminescent Agents010405 organic chemistry[CHIM.ORGA]Chemical Sciences/Organic chemistryAryl[CHIM.MATE]Chemical Sciences/Material chemistry0104 chemical sciencesSpectrometry FluorescencechemistryCarborane

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Fluorescence of Newo-Carborane Compounds with Different Fluorophores: Can it be Tuned?

2014

Two sets of o-carborane derivatives incorporating fluorene and anthracene fragments as fluorophore groups have been successfully synthesized and characterized, and their photophysical properties studied. The first set, comprising fluorene-containing carboranes 6-9, was prepared by catalyzed hydrosilylation reactions of ethynylfluorene with appropriate carboranylsilanes. The compound 1-[(9,9-dioctyl-fluorene-2-yl)ethynyl]carborane (11) was synthesized by the reaction of 9,9-dioctyl-2-ethynylfluorene and decaborane (B10H14). Furthermore, reactions of the lithium salt of 11 with 1 equivalent of 4-(chloromethyl)styrene or 9-(chloromethyl)anthracene yielded compounds 12 and 13. Members of the se…

AnthraceneHydrosilylationOrganic ChemistrySubstituentGeneral ChemistryFluorenePhotochemistryFluorescenceMedicinal chemistryCatalysisDilithiumchemistry.chemical_compoundchemistryDecaboraneCarboraneta116Chemistry - A European Journal

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A versatile methodology for the controlled synthesis of photoluminescent high-boron-content dendrimers.

2013

Fluorescent star-shaped mol- ecules and dendrimers with a 1,3,5-tri- phenylbenzene moiety as the core and 3 or 9 carborane derivatives at the pe- riphery, have been prepared in very good yields by following different ap- proaches. One procedure relies on the nucleophilic substitution of Br groups in 1,3,5-tris(4-(3-bromopropoxy)phe- nyl)benzene with the monolithium salts of methyl and phenyl-o-carborane. The second method is the hydrosilylation reactions on the peripheral allyl ether functions of 1,3,5-tris(4-allyloxy-phe- nyl)benzene and 1,3,5-tris(4-(3,4,5-tris- AAA with suitable carboranyl-silanes to produce different generations of dendrimers decorated with carboranyl fragments. This ap…

HydrosilylationOrganic ChemistrySubstituentchemistry.chemical_elementEtherGeneral ChemistryPhotochemistryCatalysischemistry.chemical_compoundchemistryDendrimerPolymer chemistryCarboraneMoietyBoronta116MacromoleculeChemistry (Weinheim an der Bergstrasse, Germany)

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Tetrakis{[(p-dodecacarboranyl)methyl]stilbenyl}ethylene: A Luminescent Tetraphenylethylene (TPE) Core System

2017

The synthesis and spectroscopic characterization of the first set of tetra(p-dodecacarborane-stilbeno)ethylenes (TDSE), substituted either with a methyl or phenyl group in the 2-position (Ccluster) of the ortho-carborane, are described. The complex absorption properties are elucidated by TD-DFT calculations, stressing the importance of through bond conjugation. Enhanced conjugation and restriction of the conformational space are identified as the main factors for boosted luminescence properties in solution compared to tetraphenylethylene (TPE) core, effectively reducing internal conversion (IC). IC is further reduced when aggregate suspensions of our compounds in water are formed, providing…

Ethylenebiology010405 organic chemistryTetraphenylethylene010402 general chemistrybiology.organism_classificationPhotochemistryInternal conversion (chemistry)01 natural sciences0104 chemical sciencesInorganic Chemistrychemistry.chemical_compoundchemistryCore systemTetraPhenyl groupAbsorption (chemistry)Luminescence

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