Gelation-Induced Enhanced Fluorescence Emission from Organogels of Salicylanilide-Containing Compounds Exhibiting Excited-State Intramolecular Proton Transfer: Synthesis and Self-Assembly

被引：67

作者：

Nayak, Manoj Kumar

Kim, Byung-Hwa ^{[1
,2
]}

Kwon, Ji Eon ^{[1
,2
]}

Park, Sanghyuk ^{[1
,2
]}

Seo, Jangwon ^{[1
,2
]}

Chung, Jong Won ^{[1
,2
]}

Park, Soo Young ^{[1
,2
]}

机构：

[1] Seoul Natl Univ, Ctr Supramol Optoelect Mat, Seoul 151744, South Korea

[2] Seoul Natl Univ, WCU Hybrid Mat Program, Dept Mat Sci & Engn, Seoul 151744, South Korea

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 25期

关键词：

fluorescence; gels; proton transfer; salicylanilides; self-assembly; LOW-MOLECULAR-MASS; FUNCTIONAL RESPONSE THEORY; EXCITATION-ENERGIES; ORGANIC LIQUIDS; METAL COORDINATION; URETHANE AMIDES; GELS; GELATORS; AM1; SALICYLIDENEANILINE;

D O I：

10.1002/chem.200902615

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：7437 / 7447

页数：11

共 95 条

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