Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 44, Pages 10005-10013Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202001566
Keywords
acid-sensitive; amphiphilic systems; pi-conjugated systems; noncovalent interactions; self-assembly
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Funding
- Humboldt foundation (Sofja Kovalevskaja Award)
- Deutsche Forschungsgemeinschaft [SFB 858]
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Besides their widespread use in coordination chemistry, 2,2'-bipyridines are known for their ability to undergo cis-trans conformational changes in response to metal ions and acids, which has been primarily investigated at the molecular level. However, the exploitation of such conformational switching in self-assembly has remained unexplored. In this work, the use of 2,2'-bipyridines as acid-responsive conformational switches to tune supramolecular polymerization processes has been demonstrated. To achieve this goal, we have designed a bipyridine-based linear bolaamphiphile, 1, that forms ordered supramolecular polymers in aqueous media through cooperative aromatic and hydrophobic interactions. Interestingly, addition of acid (TFA) induces the monoprotonation of the 2,2'-bipyridine moiety, leading to a switch in the molecular conformation from a linear (trans) to a V-shaped (cis) state. This increase in molecular distortion along with electrostatic repulsions of the positively charged bipyridine-H ' units attenuate the aggregation tendency and induce a transformation from long fibers to shorter thinner fibers. Our findings may contribute to opening up new directions in molecular switches and stimuli-responsive supramolecular materials.
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