Two types of dendrimers with a 1,3,5-triazine ring at the branch point were synthesized by divergent and convergent methods. The divergent method began with 2,4, 6-tris(p-nitroanilino)-1,3,B-triazine as a trifunctional core. Each cycle involved the reduction of the peripheral NO2 group followed by a reaction with 2-chloro-4,6-bis(p-nitroanilino)-1,3,5-triazine. The synthetic cycle was completed by the coupling with 2,4-dianilino-6-chloro-1,3,5-triazine (DACT) to eventually accomplish second-generation dendrimers ([G2](3)-C) bearing 12 benzene rings at their edge. The convergent approach started with the reaction of DACT with p-nitrophenol to give rise to 2,4-dianilino-6-(p-nitrophenoxy)-1,3, 5-triazine. The synthetic cycle consisted of reduction of the NO2 group and coupling with 2,4-dichloro-6-(p-nitrophenoxy)-1,3,5-triazine The final step was the connection of each monodendron with cyanuric chloride to produce tridendron; in this way, the second-generation dendrimer ([EG2](3)-C) was obtained. Gel permeation chromatography analyses indicated the aggregation of dendrimers in solution. Ultraviolet spectroscopic analyses revealed that the larger dendrimer had a more conjugated electron system from the core to the periphery. The thermal properties were evaluated by thermogravimetric analysis (TGA); excellent heat resistance was indicated, especially in [G1](3)-C, which included alternately imine-like nitrogen-linked 1,3,5-triazine and benzene rings.