Diaminotriazinyl-Substituted N-Heterotriangulene: Hydrogen Bonding-Driven Self-Assembly in the Solid State, in the Gas Phase and on Surfaces.

We report the synthesis and comprehensive characterization of a dimethylmethylene-bridged N-heterotriangulene (N-HTA) with diaminotriazinyl groups to guide the self-assembly through directional hydrogen bonding. Mass spectrometry collision-induced dissociation experiments indicated the formation of multiply charged clusters in the gas phase. Single crystal X-ray diffraction studies revealed that the solid state packing is governed by an interplay between the hydrogen bonding and the solvent system used for crystallization. The self-assembly on both semiconducting and insulating surfaces upon simple drop-casting was disclosed by atomic force microscopy and scanning tunneling microscopy. The strong hydrogen bonding leads to robust self-assembly on surfaces, which can be conveniently achieved by simple solution processing techniques under ambient conditions.