Synthesis of interior-functionalized dendritic macromolecules is generally tedious and labor-intensive, which has been a key factor hampering their practical applications. Here, we have revisited this long-standing challenge and devised a modular and convergent platform to synthesize multifunctional dendrons with all-carbon backbones up to four generations via an in situ functionalization strategy. Enabled by the palladium/norbornene cooperative catalysis, different functional groups can be introduced to each generation of dendrons during the dendron growth, making it convenient for systematic comparison of their properties. The utility of this versatile platform is further showcased in the internal-functionalization-dependent properties of dendrons as organogels and aggregation-induced emission materials.