A quantum chemistry study on the structure and properties of a novel stable strained cyclophane

Different levels of theoretical methods have been used to study a novel stable cyclophane 1,8-[1,8-naphthalenediylbis(4′,4-biphenyldiyl)]naphthalene. It was concluded that HF/3-21g* was the most efficient method for the system, which could well reproduce the experimental structure. In addition, HF/3-21g*//B3LYP/3-21g* calculations explained the experimental observation that the cyclophane was much easier to be oxidized to the corresponding radical cation than its related compound 1,8-bisphenyl-naphthalene. It was proposed that the more effective π-π and π-cation interactions in the radical cation of the cyclophane caused the above behavior.