<p>Cycloparaphenylenes (CPPs) possess a distinctive strained conjugated nanoring structure. These structural features impart desirable optoelectronic properties but also demand sophisticated strategies for their efficient and precise synthesis. Here we introduce an approach based on the intramolecular coupling of extended biphen[<i>n</i>]arenes (ICEB). Compared to conventional methods, the ICEB strategy transforms extended biphen[<i>n</i>]arenes into strained CPP nanorings via intramolecular reductive coupling, enhancing the synthetic efficiency while avoiding the use of noble metals. The modular nature of the extended biphen[<i>n</i>]arene building blocks used allows for the customization of the CPP structures, which in turn permits rational tuning of their photophysical properties. Using the ICEB approach, we synthesized 20 CPP derivatives of varying sizes that contain a diversity of aromatic constituents and a variety of substituents. The key macrocyclization step produced a mixture of oligomers in total yields up to 87%, while the intramolecular coupling step proceeded in up to 98% isolated yield. The CPP derivatives reported here generally exhibit intense fluorescence, with absorption and emission peaks that can be tuned by changing the ring size and aromatic subunits. Our findings highlight ICEB as an efficient, versatile and cost-effective strategy for the synthesis of CPP derivatives.</p><p></p>