Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 12, Issue 36, Pages 7110-7118Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ob00768a
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Funding
- National Natural Science Foundation of China [21103067, 21374041, 51102081]
- Youth Science Foundation of Jilin Province [20130522134JH]
- Science and Technology Development Plan of Jilin Province, China [20130521003JH]
- Open Project of the State Key Laboratory of Supramolecular Structure and Materials [SKLSSM201203]
- Open Project of State Key Laboratory of Theoretical and Computational Chemistry [K2013-02]
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A series of 4-nitrophenylacrylonitrile and phenylacrylonitrile derivatives consisting of a carbazole moiety was synthesized. Some of these derivatives with longer alkyl chains and a nitro group could gelatinize some organic solvents, such as ethanol, n-butanol, ethyl acetate, and DMSO. By contrast, phenylacrylonitrile derivatives did not form gels in measured solvents. This result proved that the electron-withdrawing nitro moiety was important for gel formation because it conferred the molecules with large dipole moments, which enhanced the intermolecular interaction. Analyses by UV-vis absorption, X-ray diffraction, and scanning electron microscopy showed that the gelator molecules could self-assemble into one-dimensional nanofibers with layer packing, which further twisted into thicker fibers and formed three-dimensional networks in the gel phase. The single crystal structure of C4CNPA implied that the gelators might adopt an anti-parallel molecular stacking because of their larger ground-state dipole moment. Interestingly, the organogels had enhanced fluorescence relative to solutions at the same concentrations.
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