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Controlling the affinity and selectivity of synthetic receptors to target desired nucleotides or short sequences is a highly challenging task. Herein, we elucidate the effect of substituents in the phenyl ring of the anthracene\u2010benzene azacyclophane on the recognition of nucleoside triphosphates (NTPs) and double\u2010stranded DNA. We show that introducing phenyl rings increases the affinity for NTPs 10\u2010fold and implements groove and intercalation binding modes with double\u2010stranded DNA. 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