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Hierarchically Ordered Self‐Assembly of Amphiphilic Bifullerenes
Author(s) -
Wasserthal Lennard,
Schade Boris,
Ludwig Kai,
Böttcher Christoph,
Hirsch Andreas
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201400153
Subject(s) - amphiphile , supramolecular chemistry , micelle , dispersity , self assembly , amphiphilic molecule , aqueous solution , molecule , covalent bond , transmission electron microscopy , materials science , crystallography , chemistry , copolymer , nanotechnology , polymer chemistry , organic chemistry , polymer
A series of novel functionalised dumbbell‐shaped bifullerenes in which two [5.0] pentakis‐adducts of C 60 are covalently connected by cyclic bismalonates were synthesised. These dimeric compounds, carrying various combinations of hydrophilic and hydrophobic addends, self‐assemble in aqueous solution towards supramolecular architectures of different structural complexity as observed by cryogenic transmission electron microscopy (cryo‐TEM). The detailed analysis of the image data revealed an unprecedented hierarchical aggregation behaviour. Whereas completely hydrophilic substituted bifullerenes formed profoundly monodisperse populations of small oligomeric elementary micelles consisting of only three or four bifullerene molecules in a supposedly bent conformation, their amphiphilic equivalents underwent a hierarchical two‐step assembly process towards larger spherical and even rod‐like structures. The data suggest that the hierarchical assembly process is driven by hydrophobic interactions of preformed tetrameric elementary micelles.