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Stimuli Responsive Materials Supported by Orthogonal Hydrogen and Halogen Bonding or I···Alkene Interaction
| Content Provider | MDPI |
|---|---|
| Author | Frangville, Pierre Kumar, Shiv Gelbcke, Michel Hecke, Kristof Van Meyer, Franck |
| Copyright Year | 2021 |
| Description | Smart materials represent an elegant class of (macro)-molecules endowed with the ability to react to chemical/physical changes in the environment. Herein, we prepared new photo responsive azobenzenes possessing halogen bond donor groups. The X-ray structures of two molecules highlight supramolecular organizations governed by unusual noncovalent bonds. In azo dye $I-azo-NO_{2}$, the nitro group is engaged in orthogonal H···O···I halogen and hydrogen bonding, linking the units in parallel undulating chains. As far as compound I–azo–NH–MMA is concerned, a non-centrosymmetric pattern is formed due to a very rare I···π interaction involving the alkene group supplemented by hydrogen bonds. The Cambridge Structural Database contains only four structures showing the same $I···CH_{2}$=C contact. For all compounds, an$ ^{19}$F-NMR spectroscopic analysis confirms the formation of halogen bonds in solution through a recognition process with chloride anion, and the reversible photo-responsiveness is demonstrated upon exposing a solution to UV light irradiation. Finally, the intermediate $I–azo–NH_{2}$ also shows a pronounced color change due to pH variation. These azobenzenes are thereby attractive building blocks to design future multi-stimuli responsive materials for highly functional devices. |
| Starting Page | 7586 |
| e-ISSN | 14203049 |
| DOI | 10.3390/molecules26247586 |
| Journal | Molecules |
| Issue Number | 24 |
| Volume Number | 26 |
| Language | English |
| Publisher | MDPI |
| Publisher Date | 2021-12-14 |
| Access Restriction | Open |
| Subject Keyword | Molecules Halogen Bonding Azobenzene Ph Sensitive Stimuli Responsive Orthogonal Interaction |
| Content Type | Text |
| Resource Type | Article |
