Self-assembled pentamers and hexamers linked through quadruple-hydrogen-bonded 2-ureido-4[1H]-pyrimidinones.
The preorganization of bifunctional 2-ureido-4-pyrimidinones mediated by either 1,3-substituted adamantane or meta-substituted phenylene ring linkers leads to the preferred formation of stable pentameric (1)(5) and hexameric (2)(6) assemblies, respectively. Despite the high binding constant of the 2-ureido-4-pyrimidinone dimers and the highly preorganized structure of the monomer, the predominant formation of cycles (1)(5) and (2)(6) in solution occurs only within a specific concentration range.
Keizer
Henk M
HM
Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, The Netherlands. e.w.meijer@tue.nl
González
Juan J
JJ
Segura
Margarita
M
Prados
Pilar
P
Sijbesma
Rint P
RP
Meijer
E W
EW
de Mendoza
Javier
J