The first example of the charged nanobelt, namely the highly-reduced [8]cycloparaphenylene, is reported. A significant batochromical shift in UV-vis spectra is seen upon reduction, illustrating substantial alteration of the electronic structure of the tetrareduced [8]CPP compared to the neutral ligand. A severe elliptic distortion of a circular core of [8]CPP upon addition of four electrons is revealed by X-ray crystallography. Moreover, the tetrareduced nanobelt functions as a versatile p-ligand for metal binding. The large cavity of [8]CPP is filled by two encapsulated potassium ions along with one THF molecule, demonstrating unique host capabilities of the negatively charged [8]CPP. The observed flexibility in changing the cavity size and shape upon charging the nanobelt with multiple electrons and metal binding may need to be accounted for during doping processes involving carbon nanotubes. This phenomenon may also allow utilization of charged [n]CPPs in host-guest separation processes through their controlled shape manipulation during redox reactions.

Tightening the nanobelt upon multielectron reduction

246th National Meeting (2013)

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