Cover Feature: O-Acylative Vinylation of Cyclodextrin-Based [3]Rotaxane Towards Rotaxane Crosslinkers (Eur. J. Org. Chem. 12/2023) |
| |
Authors: | Dr Yosuke Akae Prof?Dr Toshikazu Takata |
| |
Institution: | School of Materials and Chemical Technology, Tokyo Institute of Technology, Nagatsuta-cho 4259, Midori-ku, Yokohama, 226-8503 Japan |
| |
Abstract: | The acylation of a cyclodextrin-based 3]rotaxane was implemented with anhydride reagents following a facile procedure. Methacrylic anhydride facilitated the introduction of a vinyl-group into the rotaxane structure toward achieving a crosslinker. Interestingly, only a few methacrylic units were attached to the cyclodextrin at reaction temperatures of up to 60 °C even with an excess amount of the reagent, probably due to steric hindrance. Therefore, the number of vinyl groups on the 3]rotaxane framework was easily controlled to be approximately two units via a simple random acylation, which worked effectively as a facile synthesis route for the rotaxane crosslinker. The acylation behavior was investigated in detail by NMR and MALDI-TOF-MS analyses. Such a proposed approach will help overcome the trade-off between convenience and utility associated with the mono-modification of cyclodextrins. |
| |
Keywords: | O-acylation cyclodextrins MALDI-TOF-MS rotaxanes vinyl-group introduction |
|
|