Size-selective recognition by a tubular assembly of phenylene-pyrimidinylene alternated macrocycle through hydrogen-bonding interactions.
Langmuir
; 31(39): 10649-55, 2015 Oct 06.
Article
em En
| MEDLINE
| ID: mdl-26375477
ABSTRACT
Study of artificial tubular assemblies as a useful host scaffold for size-selective recognition and release of guest molecules is an important subject in host-guest chemistry. We describe well-defined self-assembled nanotubes (NT6mer) formed from π-conjugated m-phenylene-pyrimidinylene alternated macrocycle 16mer that exhibit size-selective recognition toward a specific aromatic acid. In a series of guest molecules, a size-matched trimesic acid (G3) gives inclusion complexes (NT6merâG3) in dichloromethane resulting in an enhanced and red-shifted fluorescence. (1)H nuclear magnetic resonance (NMR) titration experiments indicated that the complex was formed in a 11 molar ratio. Density functional theory (DFT) calculations and the binding constant value (K = 1.499 × 10(5) M(-1)) of NT6mer with G3 suggested that the complex involved triple hydrogen-bonding interactions. The encapsulated guest G3 molecules can be readily released from the tubular channel through the dissociation of hydrogen bonding by the addition of a polar solvent such as dimethylsulfoxide (DMSO). In contrast, 16mer could not form self-assembled nanotubes in CHCl3 or tetrahydrofuran (THF) solution, leading to weak or no size-selective recognizability, respectively.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Compostos Macrocíclicos
Idioma:
En
Ano de publicação:
2015
Tipo de documento:
Article