Abstract
Molecular shape recognition for larger guest molecules (typically over 1 nm) is a difficult task because it requires cooperativity within a wide three-dimensional nanospace coincidentally probing every molecular aspect (size, outline shape, flexibility and specific groups). Although the intelligent functions of proteins have fascinated many researchers, the reproduction by artificial molecules remains a significant challenge. Here we report the construction of large, well-defined cavities in macromolecular hosts. Through the use of semi-rigid dendritic phenylazomethine backbones, even subtle differences in the shapes of large guest molecules (up to ~2 nm) may be discriminated by the cooperative mechanism. A conformationally fixed complex with the best-fitting guest is supported by a three-dimensional model based on a molecular simulation. Interestingly, the simulated cavity structure also predicts catalytic selectivity by a ruthenium porphyrin centre, demonstrating the high shape persistence and wide applicability of the cavity.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Azo Compounds / chemistry*
-
Computer Simulation
-
Coordination Complexes / chemistry*
-
Dendrimers / chemistry*
-
Imaging, Three-Dimensional
-
Kinetics
-
Models, Molecular*
-
Molecular Conformation
-
Molecular Mimicry
-
Pattern Recognition, Automated*
-
Porphyrins / chemistry*
-
Ruthenium / chemistry
-
Thermodynamics
-
Zinc / chemistry
Substances
-
Azo Compounds
-
Coordination Complexes
-
Dendrimers
-
Porphyrins
-
phenylazomethine
-
Ruthenium
-
Zinc
Associated data
-
PubChem-Substance/164150132
-
PubChem-Substance/164150133
-
PubChem-Substance/164150134
-
PubChem-Substance/164150135
-
PubChem-Substance/164150136
-
PubChem-Substance/164150137
-
PubChem-Substance/164150138
-
PubChem-Substance/164150139
-
PubChem-Substance/164150140
-
PubChem-Substance/164150141
-
PubChem-Substance/164150142
-
PubChem-Substance/164150143
-
PubChem-Substance/164150144
-
PubChem-Substance/164150145
-
PubChem-Substance/164150146
-
PubChem-Substance/164150147
-
PubChem-Substance/164150148
-
PubChem-Substance/164150149
-
PubChem-Substance/164150150
-
PubChem-Substance/164150210
-
PubChem-Substance/164150211