[n]Cycloparaphenylene‐Pillar[5]arene Bismacrocycles: Their Circularly Polarized Luminescence and Multiple Guest Recognition Properties

Both pillar[n]arenes (P[n]As) and [n]cycloparaphenylenes ([n]CPPs) play an important role in supramolecular chemistry. Herein, we report the precise synthesis of two multifunctional bismacrocycles [n]CPP‐P[5]A by integrating P[5]A into the [n]CPP backbone. The photoluminescence quantum yield (ΦF) of the bismacrocycles was found to show a dramatic increase relative to the corresponding [n]CPPs. The chiral enantiomers (pR)/(pS)‐[8]CPP‐P[5]A were successfully isolated by chiral HPLC, and showed promising properties of circularly polarized luminescence (glum≈0.02). In addition, [n]CPP‐P[5]A bismacrocycles are capable of binding pyridinium salts and fullerene derivatives with high affinity and specificity within the two distinct cavities. Transient absorption studies showed that photo‐induced electron transfer occurs in [10]CPP‐P[5]A⊃C60 complex. Our results suggest that [n]CPP‐P[5]A are potentially useful in CPL‐active materials, multiple guest recognition and supramolecular polymer preparation. Bismacrocycles are presented. [n]CPP‐P[5]As show multiple guest recognition and promising properties of circularly polarized luminescence (glum≈0.02).