Provided herein are mechanically interlocked air-stable persistent organic radicals. The radical compositions may access a multiplicity of radical, cationic redox states as well as a fully cationic redox state. A composition comprises a first ring mechanically interlocked with a second ring or a salt thereof, wherein the first ring comprises a 4,4′-bipyridinium subunit or a derivative thereof and a diazapyrenium subunit or a derivative thereof and the second ring comprises a 4,4′-bipyridinium subunit or a derivative thereof. In some embodiments, the second ring further comprises a diazapyrenium subunit or a derivative thereof. Methods of preparing the compositions are also provided.
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