One-pot synthesis and AFM imaging of a triangular aramide macrocycle.
J Am Chem Soc
; 136(37): 12832-5, 2014 Sep 17.
Article
em En
| MEDLINE
| ID: mdl-25178114
ABSTRACT
Macrocyclizations in exceptionally good yields were observed during the self-condensation of N-benzylated phenyl p-aminobenzoates in the presence of LiHMDS to yield three-membered cyclic aramides that adopt a triangular shape. An ortho-alkyloxy side chain on the N-benzyl protecting group is necessary for the macrocyclization to occur. Linear polymers are formed exclusively in the absence of this Li-chelating group. A model that explains the lack of formation of other cyclic congeners and the demand for an N-(o-alkoxybenzyl) protecting group is provided on the basis of DFT calculations. High-resolution AFM imaging of the prepared molecular triangles on a calcite(10.4) surface shows individual molecules arranged in groups of four due to strong surface templating effects and hydrogen bonding between the molecular triangles.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Benzamidas
/
Hidrocarbonetos Aromáticos com Pontes
/
Compostos Macrocíclicos
Idioma:
En
Ano de publicação:
2014
Tipo de documento:
Article