Author: Albert Ferrer-ugalde

Carborane-stilbene dyads: influence of substituents and cluster isomers on the photoluminescence properties

Two novel styrene-containing meta-carborane derivatives substituted at the second carbon cluster atom (Cc) with either a methyl (Me), or a phenyl (Ph) group, are introduced herein alongside with a new set of stilbene-containing ortho- (o-) and meta- (m-) carborane dyads. The latter set of compounds has been prepared from styrenecontaining carborane derivatives via Heck coupling reaction. High regioselectivity has been achieved for these compounds by using a combination of palladium complexes [Pd2(dba)3]/[Pd(t-Bu3P)2] as a catalytic system, yielding exclusively E isomers. All compounds have been fully characterized and the crystal structures of seven of them analyzed by X-ray diffraction. Th…

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

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,…

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

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…

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

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…

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Synthesis and Characterization of New Fluorescent Styrene-Containing Carborane Derivatives: The Singular Quenching Role of a Phenyl Substituent

A set of neutral and anionic carborane derivatives in which the styrenyl fragment is introduced as a fluorophore group has been successfully synthesized and characterized. The reaction of the monolithium salts of 1-Ph-1,2-C(2)B(10)H(11), 1-Me-1,2-C(2)B(10)H(11) and 1,2-C(2)B(10)H(12) with one equivalent of 4-vinylbenzyl chloride leads to the formation of compounds 1-3, whereas the reaction of the dilithium salt of 1,2-C(2)B(10)H(12) with two equivalents of 4-vinylbenzyl chloride gives disubstituted compound 4. The closo clusters were degraded using the classical method, KOH in EtOH, to afford the corresponding nido species, which were isolated as tetramethylammonium salts. The crystal struc…

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