Premium
C 60 ‐Mediated Molecular Shape Sorting: Separation and Purification of Geometrical Isomers
Author(s) -
Rana Moumita,
Reddy R. Bharathanatha,
Rath Bibhuti Bhusan,
Gautam Ujjal K.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201408981
Subject(s) - reagent , structural isomer , supramolecular chemistry , molecule , chemistry , xylene , crystallization , cis–trans isomerism , chromatographic separation , combinatorial chemistry , materials science , chemical engineering , organic chemistry , high performance liquid chromatography , benzene , engineering
A supramolecular crystallization‐based approach has been developed for the shape‐dependent separation of geometrical isomers under near‐ambient conditions. Difficulties to separate such isomers arise because of their very similar physical properties. The present approach relies on the ability of C 60 to preferentially form solvate crystals with molecules of a specific geometry. Subsequently, these molecules are released upon mild heating to regenerate pure C 60 . By taking isomers of xylene and trimethylbenzene (TMB) as examples, we show that one of the isomers can be extracted from the rest with very high purity. To separate TMB isomers, a new C 60 –1,3,5‐TMB solvate was developed, which led to the isolation of isomer purities greater than 99.6 %. Versatility, a low operating temperature of approximately 100 °C, a separation efficiency of more than 10 weight % of C 60 per cycle, and reagent recyclability makes this a promising molecular shape‐sorting approach.