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A shape-persistent alleno-acetylenic macrocycle, peripherally decorated with eight phenolic rings, has been synthesized in enantiomerically pure form. Its electronic circular dichroism spectrum features a strong chiroptical response. In the solid state, the macrocycle stacks in pillars to form channels and the stacks undergo further self-assembly into a three-dimensional porous architecture through lateral intermolecular hydrogen-bonding.

Graphical abstract: A shape-persistent alleno-acetylenic macrocycle with a modifiable periphery: synthesis, chiroptical properties and H-bond-driven self-assembly into a homochiral columnar structure

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