Polyphenylene Dendrimers

Significance

The authors report the synthesis of polyphenylene dendrimers with highly fluorescent peryleneimide chromophores via iterative Diels-Alder cycloadditions. Two different routes were utilized for inserting peryleneimide dyes into the scaffolding of polyphenylene dendrimers. In each route, functionalization of the tetraphenylcyclopentadienone branching unit carrying two per­yleneimides is the key step resulting in a dendritic branching unit carrying two peryleneimides and two triisopropylsilyl-protected terminal alkynes for further dendritic growth. The two peryleneimide-functionalized cyclopentadienones were subsequently used to build up multichromophoric, first-generation polyphenylene dendrimers, each carrying eight peryleneimide chromophores. Construction of an asymmetric first-generation dendrimer was achieved with six PDI chromophores and one aliphatic ester.