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Tuning Aqueous Supramolecular Polymerization by an Acid‐Responsive Conformational Switch
- Source :
- Chemistry (Weinheim an Der Bergstrasse, Germany)
- Publication Year :
- 2020
-
Abstract
- 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.<br />Switch and tune! The trans–cis conformational switching of 2,2’‐bipyridine in response to acid was exploited to tune supramolecular polymerization processes. For this purpose, the aqueous self‐assembly of a bipyridine‐based linear bolaamphiphile that self‐assembles under standard conditions into cooperative supramolecular polymers was investigated. Interestingly, acid‐triggered protonation of the bipyridine unit induces a molecular conformational change from linear (trans) to cis (V‐shaped) that leads to an attenuated supramolecular growth into shorter fibers.
- Subjects :
- Supramolecular chemistry
Bolaamphiphile
010402 general chemistry
01 natural sciences
Catalysis
acid-sensitive
Hydrophobic effect
noncovalent interactions
Bipyridine
chemistry.chemical_compound
π-conjugated systems
Non-covalent interactions
Molecular switch
chemistry.chemical_classification
Full Paper
Self‐Assembly | Hot Paper
010405 organic chemistry
Chemistry
Organic Chemistry
self-assembly
General Chemistry
Full Papers
0104 chemical sciences
Supramolecular polymers
Crystallography
amphiphilic systems
Polymerization
ddc:540
Subjects
Details
- Language :
- English
- Database :
- OpenAIRE
- Journal :
- Chemistry (Weinheim an Der Bergstrasse, Germany)
- Accession number :
- edsair.doi.dedup.....8e16b0fcf9218c41e613d58cd2d31fbf