Through a dynamic polymerization and self-sorting process, a range of lowellane macrocycles have been efficiently generated in nitroaldol systems composed of aromatic dialdehydes and aliphatic or aromatic dinitroalkanes. All identified macrocycles show a composition of two repeating units, resulting in tetra-β-nitroalcohols of different structures. The effects of building block structure on the macrocyclization process have been demonstrated, and the influence from the solvent has been explored. In general, the formation of the lowellanes were amplified in response to phase-change effects, although solution-phase structures were in some cases favored. 

Spontaneous and Selective Macrocyclization in Nitroaldol Reaction Systems

Through a dynamic polymerization and self-sorting process, a range of lowellane macrocycles have been efficiently generated in nitroaldol systems composed of aromatic dialdehydes and aliphatic or aromatic dinitroalkanes. All identified macrocycles show a composition of two repeating units, resulting in tetra-β-nitroalcohols of different structures. The effects of the building block structure on the macrocyclization process have been demonstrated, and the influence from the solvent has been explored. In general, the formation of the lowellanes was amplified in response to phase-change effects, although solution-phase structures were, in some cases, favored. 

Dynamic covalent gels have been synthesized from an aromatic trialdehyde and α,ω- dinitroalkanes via the nitroaldol reaction in organic solvents. The gelation process could be finetuned by changing the starting nitroalkanes, solvents, feed concentration, catalyst loading, or reaction temperature. The resulting organogels demonstrated good structural integrity and excellent self-healing ability. Intact xerogels were produced upon drying, without damaging the network, and the solvent-free network could recover its gel form in the presence of an organic solvent. Furthermore, the crosslinked dynameric gel depolymerized to small molecules in response to excess nitromethane. This article is protected by copyright. All rights reserved.

https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/marc.202300011

Self-healable, Regenerable, and Degradable Dynamic Covalent Nitroalcohol Organogels.

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Self-healable, Regenerable, and Degradable Dynamic Covalent Nitroalcohol Organogels.