期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 16, 期 25, 页码 7437-7447出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200902615
关键词
fluorescence; gels; proton transfer; salicylanilides; self-assembly
资金
- Ministry of Education, Science and Technology [CRI
- RIAMI-AM0209(0417-20090011)]
Self-assembly structure, stability, hydrogen-bonding interaction, and optical properties of a new class of low molecular weight organogelators (LMOGs) formed by salicylanilides 3 and 4 have been investigated by field-emission scanning electron microscopy (FESEM). X-ray diffraction (XRD), UV/Vis absorption and photoluminescence, as well as theoretical studies by DFT and semiempirical calculations with CI (AM1/PECI=8) methods. It was found that salicylanilides form gels in nonpolar solvents due to pi-stacking interaction complemented by the presence of both inter- and intramolecular hydrogen bonding. The supramolecular arrangement in these organogels predicted by XRD shows lamellar and hexagonal columnar structures for gelators 3 and 4, respectively. Of particular interest is the observation of significant fluorescence enhancement accompanying gelation, which was ascribed to the formation of J-aggregates and inhibition of intramolecular rotation in the gel state.
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