An orthogonal strategy was utilized for synthesizing a novel water-soluble pillar[5]­arene ( m-TPEWP5) with tetraphenylethene-functionalized on the bridged methylene group (meso-position) of the pillararene skeleton. The obtained macrocycle exhibit both the aggregation-induced emission (AIE) effect and interesting host–guest property. Moreover, it can be made to bind with a tailor-made camptothecin-based prodrug guest (DNS-G) to form AIE-nanoparticles based on host–guest interaction and the fluorescence resonance energy transfer process for fabricating a drug delivery system. This novel type of water-soluble AIE-active macrocycle can serve as a potential fluorescent material for cancer diagnosis and therapy. In addition, the present orthogonal strategy for designing meso-functionalized aromatic macrocycles may pave a new avenue for creating novel supramolecular structures and functional materials.

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Cuboid, a basic geometric structure, has been widely applied in architecture and mathematics. In chemistry, the introduction of cuboid structures always provides a specific structural shape, enhances the stability of the structure and improves the performance of materials. Herein, a simple strategy exploiting self‐discrimination to construct a cuboid‐stacking crystal material is proposed, in which a chiral macrocycle (TBBP) based on Tröger's base (TB) and benzophenone (BP) was synthesized as the building element of the cuboid. The cuboid is designed to be transformable compared with cuboid structures in previous work. For this reason, it is considered that the cuboid‐stacking structure can be transformed through external stimulation. Iodine vapor is selected as the external stimulus to transform the cuboid‐stacking structure due to the favorable interaction between iodine and the cuboid. The changes in the stacking mode of TBBP is studied by single‐crystal X‐ray diffraction (SCXRD) and powder X‐ray diffraction (PXRD). To our surprise, this Tröger's base‐based cuboid shows strong iodine adsorption capacity up to 3.43 g g−1 and exhibits potential as a crystal material for iodine adsorption.

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