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Diphenanthrioctaphyrin(1.1.1.0.1.1.1.0): conformational switching controls the stereochemical dynamics of the topologically chiral system.
Autorzy
Rok wydania
2019
Czasopismo
Journal of the American Chemical Society
Numer woluminu
141
Strony
6060-6072
DOI
10.1021/jacs.9b01357
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
The analogue of octaphyrin(1.1.1.0.1.1.1.0) bearing two dimethoxyphenanthrene units was synthesized and characterized in solution and solid state. The macrocycle was demonstrated to exist as two locked conformers that can be easily separated and handled individually. The conversion of conformers was proven to be facilitated by the presence of hydrogen-bond acceptors, such as amines. The bis-boron(III) complex of diphenanthrioctaphyrin has been obtained, proving that the metalloid center acts as the topology selector stabilizing only one conformation of the macrocycle, irrespective of the stereoisomer used for the insertion. Both conformers of diphenanthrioctaphyrin, as well as the boron complex formed from them, have been separated into enantiomers using HPLC with a chiral stationary phase. All of these systems have shown strikingly different stereodynamic behavior.
Adres publiczny
http://dx.doi.org/10.1021/jacs.9b01357