Synthesis of Fluorescent Dendrimers with an Oligo(phenylenevinylene) Core

Domínguez-Chávez, Jorge G.; Lijanova, Irina V.; Moggio, Ivana; Arias, Eduardo; Vázquez-García, Rosa Ángeles; Reyes-Valderrama, María Isabel; Klimova, Tatiana; Gutiérrez-Nava, Manuel; Martínez‐García, Marcos

doi:10.1166/jnn.2007.616

Cited by 10 publications

(7 citation statements)

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“…Karstedt’s catalyst (platinum divinyltetramethyldisiloxane complex, 2.1−2.4% platinum in vinyl terminated polydimethylsiloxane) was obtained from ABCR and used as received. Compounds 1 , 3 , 4a , 6 , 3,4,5-trisallyloxy(benzyloxy)benzene, 8 , and 9 were prepared according to the literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Polyanionic Aryl Ether Metallodendrimers Based on Cobaltabisdicarbollide Derivatives. Photoluminescent Properties

et al. 2009

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Fluorescent Fréchet-type poly(aryl ether) dendrimers that incorporate the 1,3,5-triphenylbenzene as core molecule and 3, 6, 9, or 12 terminal allyl ether groups have been prepared in very good yield by following the Fréchet convergent approach. Regiospecific hydrosylilation reactions on the allyl ether functions with the cobaltabisdicarbollide derivative Cs[1,1′-μ-SiMeH-3,3′-Co(1,2-C2B9H10)2] lead to different generations of Féchet-type polyanionic metallodendrimers decorated with 3, 6, and 9 cobaltabisdicarbollide units. Starting dendrimers exhibit photoluminescence properties at room temperature under ultraviolet irradiation; nevertheless, after functionalization with cobaltabisdicarbollide derivatives, the fluorescence properties are quenched. Products are fully characterized by FTIR, NMR, and UV−vis spectroscopies. For metallodendrimers, the UV−vis absorptions have been a good tool for estimating the experimental number of cobaltabisdicarbollide units peripherally attached to the dendrimeric structure and consequently to corroborate the unified character of the dendrimers. Because of the anionic character of these compounds and the boron-rich content, we actually focus our research on biocompatibility studies and potential applications.

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Section: Methodsmentioning

confidence: 99%

Polyanionic Aryl Ether Metallodendrimers Based on Cobaltabisdicarbollide Derivatives. Photoluminescent Properties

et al. 2009

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“…These compounds should allow a facilitated introduction into the compound to be labelled without severe structural alteration of the carrier. The multimeric fluorescent substances synthesised so far are merely used as chemosensors for H + or metal ions, [27][28][29][30][31] optical brighteners [32,33] or potential compounds for organic light-emitting diodes [34,35] because they are either insoluble in water-containing systems or cannot be introduced into a biocompatible carrier molecule.…”

Section: Introductionmentioning

confidence: 99%

PAMAM Structure‐Based Multifunctional Fluorescent Conjugates for Improved Fluorescent Labelling of Biomacromolecules

Wängler

Moldenhauer

Saffrich

et al. 2008

Chemistry A European J

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Fluorescent probes are of increasing interest in medicinal and biological applications for the elucidation of the structures and functions of healthy as well as tumour cells. The quality of these investigations is determined by the intensity of the fluorescence signal. High dye/carrier ratios give strong signals. However, these are achieved by the occupation of a high number of derivatisation sites and therefore are accompanied by strong structural alterations of the carrier. Hence, polyvalent substances containing a high number of fluorescent dyes would be favourable because they would allow the introduction of many dyes at one position of the compound to be labelled.A large number of different dyes have been investigated to determine the efficiency of coupling to a dendrimer scaffold and the fluorescence properties of the oligomeric dyes, but compounds that fulfil the requirements of both strong fluorescence signals and reactivities are rare. Herein we describe the synthesis and characterisation of dye oligomers containing dansyl-, 7-nitro-2,1,3-benzoxadiazol-4-yl- (NBD), coumarin-343, 5(6)-carboxyfluorescein and sulforhodamine B2 moieties based on polyamidoamine (PAMAM) dendrimers. The PAMAM dendrimers were synthesised by an improved protocol that yielded highly homogeneous scaffolds with up to 128 conjugation sites. When comparing the fluorescent properties of the dye oligomers it was found that only the dansylated dendrimers met the requirements of enhanced fluorescence signals. The dendrimer containing 16 fluorescent dyes was conjugated to the anti-epidermal-growth-factor receptor (EGFR) antibody hMAb425 as a model compound to show the applicability of the dye multimer compounds. This conjugate revealed a preserved immunoreactivity of 54%.We demonstrate the applicability of the dye oligomers to the efficient and applicable labelling of proteins and other large molecules that enables high dye concentrations and therefore high contrasts in fluorescence applications.

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“…The spectral data of 3 was compared with that already published. 5,12 1,3,5-Tris-[3,5-bis(allyloxy)benzyloxy]benzene (6). To a round bottom flask containing K2CO3 (1.53 g, 11.1 mmol) in DMF:THF (60:12 mL) as solvent, under nitrogen atmosphere, was added phloroglucinol 5 (0.20 g, 1.23 mmol) and the mixture was heated at 70 °C followed by addition of 3,5-diallyloxybenzyl chloride 2 (0.88 g, 3.69 mmol).…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Synthesis of Fréchet-type poly(aryl ether) dendrimers with allyl end groups: comparative convergent and divergent approaches

Magaña-Vergara

Soto-Castro

Vázquez‐Lima

et al. 2017

Arkivoc

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The high versatility of allyl groups at the dendrimer periphery makes it important to improve the methodologies to obtain them. Fréchet-type poly(aryl ether) first and second generation dendrimers bearing a conjugated phloroglucinol core with 6 or 12 peripheral allyl groups have been synthesized by convergent and divergent approaches. By the divergent approach the dendrimers were obtained in higher yields and product purification was easier. Steric hindrance proved not to be the key factor in achieving higher yields in the divergent approach; MM and DFT analysis corroborate that electronic effects on the alkoxide play a key role.

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Synthesis of Fluorescent Dendrimers with an Oligo(phenylenevinylene) Core

Cited by 10 publications

References 0 publications

Polyanionic Aryl Ether Metallodendrimers Based on Cobaltabisdicarbollide Derivatives. Photoluminescent Properties

Polyanionic Aryl Ether Metallodendrimers Based on Cobaltabisdicarbollide Derivatives. Photoluminescent Properties

PAMAM Structure‐Based Multifunctional Fluorescent Conjugates for Improved Fluorescent Labelling of Biomacromolecules

Synthesis of Fréchet-type poly(aryl ether) dendrimers with allyl end groups: comparative convergent and divergent approaches

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