Creation of Chiral Thixotropic Gels through a Crown-Ammonium Interaction and their Application to a Memory-Erasing Recycle System

A unique class of oligothiophene‐based organogelator bearing two crown ethers at both ends was synthesized. This compound could gelatinize several organic solvents, forming one‐dimensional fibrous aggregates. From the observation of circular dichroism, it was confirmed that the helical handedness of...

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Bibliographic Details
Published in:Chemistry : a European journal 2012-03, Vol.18 (10), p.2832-2838
Main Authors: Sobczuk, Adam A., Tsuchiya, Youichi, Shiraki, Tomohiro, Tamaru, Shun-ichi, Shinkai, Seiji
Format: Article
Language:English
Subjects:
Chemistry
Chirality
Circular Dichroism
Circularity
crown compounds
Crown ethers
Crown Ethers - chemical synthesis
Crown Ethers - chemistry
Data storage
Dichroism
Gels - chemical synthesis
Gels - chemistry
Handedness
Memory devices
Models, Molecular
Molecular Structure
Quaternary Ammonium Compounds - chemistry
self-assembly
sol-gel processes
supramolecular chemistry
Switching
Thiophenes - chemical synthesis
Thiophenes - chemistry
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Summary:A unique class of oligothiophene‐based organogelator bearing two crown ethers at both ends was synthesized. This compound could gelatinize several organic solvents, forming one‐dimensional fibrous aggregates. From the observation of circular dichroism, it was confirmed that the helical handedness of the fibrous assembly is controllable by the chirality of 1,2bisammonium guests, thus suggesting that one guest molecule bridges two gelator molecules through the crown–ammonium interaction. Interestingly, we have found that such chirality is created by thermal gelation, whereas it disappears by thixotropic gelation. The new finding implies that the present organogel system is applicable as a reversible switching memory device, featuring memory creation by a heat mode and memory erasing by a mechanical mode. Chiral memory switching: A unique class of functional organogelator based on crown ether appended oligothiophene was created, the chirality of which was influenced by the interaction with chiral ammonium guests. Stimuli‐induced circular dichroism with controlled handedness of aggregates was observed. The reversibility of thixotropic/thermal behaviors can be applied to chirality switching memory devices (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201103249