Answers are grounded in this paper and cite their sources.
The long and short of it: Gemini surfactants with a non-Hückel diaza[12]annulene core have been synthesized (see picture). DFT computations give a minimum-energy conformation with alternate shorter and longer bonds, and with the two N substituents pointing away from each other. Studies on the aggregation of the molecules in water show they encounter packing difficulties, with no evidence for ring/ring interactions at the micelle surfaces.
No takes yet. Share an insight, caveat, or question.
Shi et al. (2007) studied this question.
Synapse has enriched 10 related papers. Consider them for comparative context: