Beilstein J. Org. Chem.2013,9, 2715–2750, doi:10.3762/bjoc.9.308
mechanistic proposals: computational and experimental evidence
The groups of Fokin and Finn have tested different heterocyclic chelating ligands for CuAAC by fluorescence quenching in the reaction of dansyl azide fluorophore and dabsyl alkyne, and carried out kinetic measurements with a bis
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Graphical Abstract
Scheme 1:
Exemplary 1,3-dipolar cycloaddition of phenylacetylene with phenyl azide [6].
Beilstein J. Org. Chem.2011,7, 1577–1583, doi:10.3762/bjoc.7.186
Functionalized phenols based on tyramine were synthesized in order to be selectively grafted on to hexachlorocyclotriphosphazene, affording a variety of functionalized dendrons of type AB5. The B functions comprised fluorescent groups (dansyl) or dyes (dabsyl), whereas the A function was provided by either an
aldehyde or an amine. The characterization of these dendrons is reported. An unexpected behaviour of a fluorescent and water-soluble dendron based on dansyl groups in mixtures of dioxane/water was observed.
Keywords: dabsyl; dansyl; dendrimer; dendron; fluorescence; Introduction
Dendrimers constitute an
[15]. The method elaborated is also useful for the grafting of dyes, as will be illustrated with the dabsyl dye. We also paid particular attention to the nature of the remaining function (usable for the grafting of the dendron). We choose an aldehyde and a primary amine, both being well-known for
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Graphical Abstract
Scheme 1:
Synthesis of functionalized phenols. Reagents and conditions: a) Boc2O, 1.0 equiv, THF, 0 °C → rt, ...