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opyright. All rights reserved.Novel BN-doped compounds based on chiral, tetrasubstituted [2.2]paracyclophane and NBN-benzo[f,g]tetracene were synthesized by Sonogashira-Hagihara coupling. Conjugated ethynyl linkers allow electronic communication between the π-electron systems through-bond, whereas through-space interactions are provided by strong π-π overlap between the pairs of NBN-building blocks. Excellent optical and chiroptical properties in racemic and enantiopure conditions were measured, with molar absorption coefficients up to ϵ=2