I will present the synthesis of four-, six- and eight-membered tetraphenylethylene (TPE)-based macrocycles on Ag(111) via on-surface Ullmann coupling reactions. Their unique chemical and physical properties, such as intrinsic inner cavities and aromaticity/antiaromaticity make these systems appealing building blocks for functional supramolecular materials. The as-synthesized macrocycles are spontaneously segregated on the surface and self-assemble as large-area two-dimensional mono-component supramolecular crystals. Combined in-situ characterized by scanning tunneling spectroscopic and computational analysis evidence that the macrocycles undergo structural and orbital symmetry breaking due to extended conjugation in the macrocycles.
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Li et al. (2024) studied this question.
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