Journal
CHEMPLUSCHEM
Volume 79, Issue 1, Pages 35-44Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cplu.201300108
Keywords
-
Categories
Funding
- Japan Society for the Promotion of Science (JSPS)
- Ministry of Education, Culture, Sports, Science, and Technology, Japan
- JSPS [P06350, 9164]
- Grants-in-Aid for Scientific Research [23550151, 13J00480] Funding Source: KAKEN
Ask authors/readers for more resources
Optically active amidine ((R)-1) and achiral carboxylic acid (2) dimers with a m-terphenyl backbone linked by a 1,4-phenylene diacetylene unit form a double helix, (R)-1.2, through complementary amidinium-carboxylate salt bridges in THF. Upon the addition of poor solvents, such as n-hexane, the duplex forms an organogel as a result of supramolecular polymerization of the duplex by intermolecular rearrangement of the salt bridges. In sharp contrast, an analogous racemic duplex composed of achiral amidine residues and an optically active duplex linked by a shorter diacetylene unit with a higher binding affinity than that of (R)-1.2 does not show any gelation. The supramolecular fluorescent gels exhibit reversible thermoand chemoresponsive behavior. The chiroptical properties of the gels, the mechanism of gelation, and the amplification of helical chirality during the gelation of (R)-1.2 in the absence and presence of its enantiomeric counterpart, (S)-1.2, and a racemic duplex, consisting of achiral amidine and carboxylic acid dimers, were investigated by following changes in the absorption and circular dichroism spectra.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available