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 (|g_lum|=1.68×10^-3) and well-define cavity for hosting electron-deficient or positively charged guests with K_a up to 1.7×10⁶ M^-1.