Highly strained [6]cycloparaphenylene: crystallization of an unsolvated polymorph and the first mono- and dianions

An X-ray diffraction study of [6]cycloparaphenylene (1), crystallized under solvent-free conditions, revealed a unique solid state structure with tight packing of individual molecules that minimizes empty internal space. The controlled chemical reduction of this highly strained nanohoop with Group 1 metals resulted in the first isolation and structural characterization of its mono- and dianions, allowing for the evaluation of core transformations for the series ranging from 1(0) to 1(1-) and 1(2-).