Guanidine cyclic diimides and their polymers

We report the formation and degradation of a unique guanidine cyclic diimide (GCDI) structure and GCDI-based polymers. The GCDI structure is readily formed under mild conditions. The X-ray crystal structure showed that the delocalized p-orbitals in the guanidine plane are significantly disrupted in the GCDI structure. Unlike amine-based imides, the GCDI structure readily degrades into the initial guanidine in protic solvents at ambient temperatures. Furthermore, poly(GCDI)s, a new category of polymers with the GCDI backbones, can be synthesized from guanidines and dianhydrides. Similar to the monomeric GCDIs, poly(GCDI) s are degraded in protic solvents unlike polyimides with high chemical stability.