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The Role of Peripheral Amide Groups as Hydrogen‐Bonding Directors in the Tubular Self‐Assembly of Dinucleobase Monomers
Author(s) -
VázquezGonzález Violeta,
Mayoral María J.,
Aparicio Fátima,
MartínezArjona Paula,
GonzálezRodríguez David
Publication year - 2021
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.202100255
Subject(s) - supramolecular chemistry , amide , polymerization , monomer , hydrogen bond , self assembly , supramolecular polymers , chemistry , materials science , polymer chemistry , nanotechnology , molecule , polymer , organic chemistry
Nanotubes are a fascinating kind of self‐assembled structure which have a wide interest and potential in supramolecular chemistry. We demonstrated that nanotubes of defined dimensions can be produced from dinucleobase monomers through two decoupled hierarchical cooperative processes: cyclotetramerization and supramolecular polymerization. Here we analyze the role of peripheral amide groups, which can form an array of hydrogen bonds along the tube axis, on this self‐assembly process. A combination of 1 H NMR and CD spectroscopy techniques allowed us to analyze quantitatively the thermodynamics of each of these two processes separately. We found out that the presence of these amide directors is essential to guide the polymerization event and that their nature and number have a strong influence, not only on the stabilization of the stacks of macrocycles, but also on the supramolecular polymerization mechanism.