Synthesis and C60 Binding of Aza[10]CPP and N-Methylaza[10]CPP

Within the growing family of strained carbon nanohoops and nanobelts, [10]CPP arguably offers best compromise between synthetic accessibility strong binding affinity for C60. In this work, we report synthesis two nitrogen-containing analogues systematically compare structure, optoelectronic properties C60 affinities small set structurally similar macrocycles. While Aza[10]CPP outcompetes parent compound by approximately one order magnitude with respect to binding, found that reverse was true methylaza analogue. Transient absorption studies showed photo-induced electron transfer occurred readily from its aza-analogue an encapsulated guest. Formation a charge-separated complex not observed however N-methylated derivative. These insights will prove useful further applications in supramolecular chemistry organic electronics.