Rapidly Exchanging, Double-Dynamic, Catalyst-Free Nitroaldol-Hemiacetal Systems for Metal-Responsive Reversible Polymerization

• A spontaneous, catalyst-free, reversible nitroaldol reaction is reported. The reaction wasused to create dynamic systems and to evaluate their scope and applicability. The thermodynamicand kinetic properties of the reaction were estimated, showing substantial solvent effects andatypical behavior regarding fluctuations and conversion overshoots. This was especially the casewhere the dynamic process was coupled with hemiacetal formation. Multifunctional building blockswere furthermore explored to generate responsive molecular systems, where zinc-coordinationcould be used to downregulate the nitroaldol reaction through the amplification of a dihemiacetalspecies. The systems were also extended to dynamic oligomer formation, where the molecularweight could be predictably upregulated by concentration increase and downregulated throughmetal coordination-induced amplification.

Subject headings

NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)

Publication and Content Type

vet (subject category)

ovr (subject category)