Evidence for fully conjugated double-stranded cycles

Abstract

A chain of circumstantial evidence for the existence of the first fully conjugated, double-stranded cycles is presented. The products have the structure of the belt-region of fullerene C(84)(D(2)) and carry either four hexyl chains or four phenyl groups. The unsubstituted parent cycle is also presented. The chain of evidence is mainly based on mass spectrometric analysis and trapping reactions, the latter being supported by quantum mechanical calculations. It is also of importance that the phenyl-substituted and unsubstituted products cannot undergo a [1,5] hydrogen shift, the only reasonable side-reaction that recently could not be excluded for the alkyl-substituted analogue. It is concluded that the fully aromatic targets truly exist in the gas phase. Whether they can be generated in solution under the applied conditions cannot yet be firmly decided; theoretical evidence speaks against.