Dendrimers Clicked Together Divergently

Abstract

Dendrimers containing 1,4-triazole linkages between each generation were grown divergently via the Click chemistry inspired Huisgen 1,3-dipolar cycloaddition reaction in the presence of a Cu(I) catalyst. The monomeric unit (1-propargylbenzene-3,5-dimethanol) contained the alkyne functionality, while the core (1,2-bis(2-azidoethoxy)ethane) and growing dendrimers presented the azide groups necessary for this type of Click reaction. The first generation dendrimer was also functionalized with alkyne termini to demonstrate an alternative pathway allowed by this chemistry. Synthesis and characterization, with infrared (IR), 1 H and 13 C NMR spectroscopies, high-resolution mass spectrometry, gel permeation chromatography (GPC), differential scanning calorimetry (DSC), and thermogravimetric analysis (TGA), are reported for these divergently grown dendrimers.

New methodologies in the construction of dendritic materials

“…Subsequently, Wooley et al 30 reported on the divergent growth approach to Fre´chet-type dendrimers using Click chemistry, resulting in either azide or acetylene terminated dendrimers.…”

Click Chemistry: Versatility and Control in the Hands of Materials Scientists

“…Since then, this Huisgen cycloaddition has been widely employed to synthesize or modify various dendrimers. [11,14,15,[55][56][57][58][59][60][61] Similarly, Diels-Alder reactions have found application in dendrimer synthesis and modification. McElhanon and Wheeler prepared dendrons and dendrimers that had thermoresponsive properties, owing to the reversibility of the Diels-Alder reaction.…”

Glycodendritic structures: tools to interact with DC-SIGN

“…The click chemistry reaction CuAAC is a very efficient, versatile, and popular reaction that has found several applications in many fields to achieve the preparation of very diverse molecules ranging from small compounds to polymers, hydrogel and other larges entities, including dendrimers (Wu et al, 2004;Joralemon et al, 2005;Malkoch et al, 2005;Fernández-Megia et al, 2006;Franc, Kakkar, 2010). Following a convergent strategy based on CuAAC reaction, the synthesis of a new class of glycodendrons with full control of the structure was developed.…”