Investigating the Reactivity of 1,4-Anthracene-Incorporated Cycloparaphenylene.

Cycloparaphenylenes (CPPs) and their derivatives are unique conjugated macrocycles with novel optoelectronic and host-guest properties. A better understanding of their reactivity is essential for creating new functional materials utilizing these strained aromatic molecules as building blocks. 1,4-Anthracene-incorporated CPP 1 was synthesized and exhibited Diels-Alder reactivity but was unable to photodimerize. Comparison studies with cyclophane 2 and unstrained 3 indicated that the distorted anthracene geometry is likely the major contributor to the anomalous reactivity of 1.