Three series of dendrimers were synthesized divergently via combination of orthogonal Passerini reaction and thiol-yne reaction. First, the Passerini reaction of propargyl isocyanoacetamide, 6-heptynoic acid, and <i>o</i>-nitrobenzaldehyde derivative provided the G0 dendrimer with three terminal alkyne groups. Then, G0 dendrimer was allowed to react with 3-mercaptopropionic acid with AIBN as the thermal initiator to get the G1 dendrimer with six terminal carboxylic acid groups. Repeating these two steps with 5-hexyn-1-al and phenylacetaldehyde for the Passerini reaction can finally generate the G3.5 dendrimer with the photolabile <i>o</i>-nitrobenzyl ester group in the core. Due to the high efficiency and orthogonal nature of the two reactions, this strategy shows several advantages like diverse structures, easy purification, and simple operation. UV degradation of the dendrimers was studied, and the rates of photolysis reactions of different dendrimers were compared. The efficient synthesis of dendrimers and incorporation of photolabile groups provide new opportunities to access functional materials suitable for different applications.

Efficient synthesis of diverse core photolabile dendrimers via combination of Passerini reaction and thiol-yne reaction

250th National Meeting (2015)

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