A silacyclophane molecule with two disilanyl pillars and two oligoarylene units was synthesized. The molecule was packed in a single crystal with a new motif interfusing π-stack and herringbone packing structures. The hole transporting ability of the solid was revealed by using the flash-photolysis time-resolved microwave conductivity method. The molecular structure, albeit a singly-bonded arylene macrocycle, was rigidified by the unique packing array, which favorably contributed to the hole transporting ability of the solid via the small reorganization energy through the charge transport. Packed in like herrings: A cyclophane molecule with disilanyl pillars was synthesized by using ternaphthyl as base arylene units to afford a macrocycle possessing interfused packing structures of π-stack and herringbone motifs.
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