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Opposite Enantioselectivity by Nanotubes and Nanospheres Self‐Assembled from Dirhodium(II) and an l ‐Glutamic Acid Terminated Bolaamphiphile
Author(s) -
Yuan Chenhuan,
Jiang Jian,
Sun Hui,
Wang Decai,
Hu Yonghong,
Liu Minghua
Publication year - 2018
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201800081
Subject(s) - supramolecular chemistry , chirality (physics) , supramolecular chirality , enantioselective synthesis , chemistry , self assembly , catalysis , combinatorial chemistry , stereochemistry , organic chemistry , molecule , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
Coordination is an important factor that can be used to modulate the structure and function of self‐assembly systems. Herein, we report the coordination‐regulated self‐assembly of chiral nanostructures and their enantioselective catalytic performances. We found that if a rhodium complex and an l ‐glutamic acid terminated bolaamphiphile were self‐assembled by coordination, single‐walled nanotubes and nanospheres could be obtained depending on the molar ratio. Interestingly, the nanotubes and nanospheres showed opposite supramolecular chirality even though the same chiral bolaamphiphile was used. If the nanospheres and nanotubes were used as catalysts for the asymmetric cyclopropanation reaction, opposite enantioselectivities were obtained, which indicated that it was the supramolecular chirality rather than the molecular chirality that controlled the enantioselectivity of the asymmetric reaction. This work provides not only a feasible method to construct different nanostructures through metal coordination but also a new pathway of transferring chirality from the supramolecular level to chiral products.