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- Title
Fullerene Building Blocks with Tailor‐Made Solubility and New Insights into Their Hierarchical Self‐Assembly.
- Authors
Pérez‐Ojeda, M. Eugenia; Wabra, Isabell; Böttcher, Christoph; Hirsch, Andreas
- Abstract
Abstract: Herein, the synthesis of fullerene derivatives with adjustable polarities and lyotropic aggregation properties is reported. The polarity range spans from superhydrophobic to hydrophilic, while simultaneously providing a further reactive position with a view to graft them onto other materials. The synthetic strategy relies on a selective protection with an isoxazoline moiety. The remaining octahedral positions were further functionalized with the desired groups to tune their solubility, yielding mixed [5:1] hexakisadducts. The subsequent deprotection by clean photolytic reaction led to fullerene pentakisadducts with an incomplete octahedral addition pattern, which are useful forerunners for the synthesis of building blocks. Their hydrophobic/hydrophilic behavior has been characterized both in solution and surface through octanol/water partition coefficients (log P) and contact angle measurements. Furthermore, these derivatives can form supramolecular constructions which have been studied by dynamic light scattering (DLS) and cryo‐TEM.
- Subjects
FULLERENES; SUPERHYDROPHOBIC surfaces; ISOXAZOLINE; SUPRAMOLECULAR chemistry; LIGHT scattering
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 53, p14088
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201803036