Abstract Four novel triphenylene-Bodipy dyads were synthesized in yields of 32–38% and characterized by MS, NMR, elemental analysis. They exhibit good columnar liquid crystal behaviors at room temperature. The alkyl substitution on the Bodipy unit does not cause the disruption of the mesophase. They possess excellent fluorescence properties with high quantum yields in solution and the weak fluorescence in film. The alkyl substitutions on the Bodipy unit increase the fluorescence intensity and the introduction of triphenylene units reduce the aggregation-caused quenching of orderly stacking of Bodipy units.