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Self‐Assembled Pentamers and Hexamers Linked through Quadruple‐Hydrogen‐Bonded 2‐Ureido‐4[1 H ]‐Pyrimidinones
Author(s) -
Keizer Henk M.,
González Juan J.,
Segura Margarita,
Prados Pilar,
Sijbesma Rint P.,
Meijer E. W.,
de Mendoza Javier
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200500329
Subject(s) - pyrimidinones , chemistry , monomer , bifunctional , stereochemistry , crystallography , random hexamer , ring (chemistry) , adamantane , combinatorial chemistry , polymer chemistry , organic chemistry , polymer , catalysis
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.
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