Stable organic radicals with unique luminescence show great importance in photoelectromagnetic materials. We herein report two unusual radical-based systems ( and ) using the concerted effects of planar chiral pillar[5]arenes and tris(2,4,6-trichlorophenyl)methyl () radicals. The steric effect and electronic doublet-spin character of these radicals allowed the optical resolution and the first red emissions (∼650 nm) for pillar[5]arene derivatives. Notably, cross-coupling with macrocyclic pillar[5]arene, in turn, considerably enhanced the configurational stability of radicals.
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