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ortho-Nitrosocumene (o-NC) exhibits dynamic N,N bonding, interchanging monomer and E/Z-azodioxide dimer structures, the extent of which depends on the environment. As a solid, o-NC is a Z-dimer; in organic solvent, the monomer is favored; and in water, dimers are favored. A supramolecular assembly of o-NC is observed as a separate species by NMR in water, shown to be a novel nanometer-sized aggregate containing B2000 molecules. 

Photobase generators (PBGs) are compounds that utilize light-sensitive chemical-protecting groups to offer spatiotemporal control of releasing organic bases upon targeted light irradiation. PBGs can be implemented as an external control to initiate anionic polymerizations such as thiol–ene Michael addition reactions. However, there are limitations for common PBGs, including a short absorption wavelength and weak base release that lead to poor efficiency in photopolymerization. Therefore, there is a great need for visible-light-triggered PBGs that are capable of releasing strong bases efficiently. Here, we report two novel BODIPY-based visible-light-sensitive PBGs for light-induced activation of the thiol–ene Michael “click” reaction and polymerization. These PBGs were designed by connecting the BODIPY-based light-sensitive protecting group with tetramethylguanidine (TMG), a strong base. Moreover, we exploited the heavy atom effect to increase the efficiency of releasing TMG and the polymerization rate. These BODIPY-based PBGs exhibit extraordinary activity toward thiol–ene Michael addition-based polymerization, and they can be used in surface coating and polymer network formation of different thiol and vinyl monomers.