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- Title
Harnessing Polyisobutylene by Rotaxanation with γ‐Cyclodextrin: Opportunities for Making Smart Molecular Necklaces.
- Authors
Przybylski, Cédric; Ramoul, Hassen; Bonnet, Véronique; Abad, Mathilde; Jarroux, Nathalie
- Abstract
A new type of polyrotaxane based on the threading of γ‐cyclodextrins (γ‐CDs) along a highly hydrophobic polymer, polyisobutylene (PIB), is successfully prepared and finely characterized. The used radical coupling associated with tuned reaction time and temperature leads to a fast and controlled necklace synthesis with low reagent consumption. Synthesis exhibits appealing conversion and threading rates with almost 100% and 62–73%, respectively. A combination of well‐established SEC and NMR techniques, with a more forefront MALDI‐TOF MS approach, provides details on the original PIB and the resulting polyrotaxanes (Mw, Mn, PDI, and average number of γ‐CD threaded). Interestingly, tetramethylguanidinium‐2‐(4‐hydroxyphenylazo)benzoate in DMF for MALDI analysis is revealed as a suitable matrix to overcome solubility troubles widely observed with PIB. Moreover, rotaxanation appears as an alternative to the grafting of polar groups to modify/handle hydrophobic polymers. Such an approach offers new opportunities to achieve the synthesis, with unambiguous evidence, of new supramolecular necklaces based on highly hydrophobic polymers. Polyrotaxane based on γ‐cyclodextrins threaded along a polyisobutylene backbone is successfully synthesized and finely characterized. An optimized radical coupling leads to fast and controlled necklace synthesis with conversion and threading rates close to 100% and 62–73%, respectively. All starting materials as well as resulting necklaces are analyzed by SEC, NMR, and MALDI‐TOF MS, giving unambiguous evidences of the successful synthesis.
- Subjects
ROTAXANES; BUTENE; CYCLODEXTRINS; HYDROPHOBIC compounds; NUCLEAR magnetic resonance spectroscopy
- Publication
Macromolecular Chemistry & Physics, 2019, Vol 220, Issue 5, pN.PAG
- ISSN
1022-1352
- Publication type
Article
- DOI
10.1002/macp.201800502