Enantiopure Macrocycles Based on Tröger's Base and Diphenyl Maleimide Exhibiting Strong Chiral Emission and Host‐guest Properties

While a plenty of macrocyclic hosts have been developed in supramolecular chemistry, those that combine chiral luminescent properties and host‐guest recognition abilities are still uncommon. Herein, two pairs of enantiomeric macrocycles were synthesized via Suzuki‐Miyaura [2+2] cyclization reactions using Tröger's base and diphenyl maleimide as the building blocks. The diphenyl maleimide units impart these macrocycles with highly strong fluorescence, achieving quantum yields up to 100% in apolar solvents. Furthermore, the chiral, V‐shaped Tröger's base units provide the macrocycles with circularly polarized luminescence (|glum| = 1.68 × 10−3) and well‐define cavity for hosting electron‐deficient or positively charged guests with Ka up to 1.7 × 106 M−1.