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

Authors

  • Manoj Kumar Nayak Dr.,

    1. Current address: Department of Chemistry, Texas A&M University at Qatar, PO Box 23874, Doha (Qatar)
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  • Byung-Hwa Kim,

    1. Center for Supramolecular Optoelectronic Materials and WCU Hybrid Materials Program, Department of Materials Science and Engineering, Seoul National University, ENG 445, San 56-1, Shillim-dong, Kwanak-ku, Seoul 151-744 (Korea), Fax: (+82) 2-886-8331
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  • Ji Eon Kwon,

    1. Center for Supramolecular Optoelectronic Materials and WCU Hybrid Materials Program, Department of Materials Science and Engineering, Seoul National University, ENG 445, San 56-1, Shillim-dong, Kwanak-ku, Seoul 151-744 (Korea), Fax: (+82) 2-886-8331
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  • Sanghyuk Park Dr.,

    1. Center for Supramolecular Optoelectronic Materials and WCU Hybrid Materials Program, Department of Materials Science and Engineering, Seoul National University, ENG 445, San 56-1, Shillim-dong, Kwanak-ku, Seoul 151-744 (Korea), Fax: (+82) 2-886-8331
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  • Jangwon Seo Dr.,

    1. Center for Supramolecular Optoelectronic Materials and WCU Hybrid Materials Program, Department of Materials Science and Engineering, Seoul National University, ENG 445, San 56-1, Shillim-dong, Kwanak-ku, Seoul 151-744 (Korea), Fax: (+82) 2-886-8331
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  • Jong Won Chung,

    1. Center for Supramolecular Optoelectronic Materials and WCU Hybrid Materials Program, Department of Materials Science and Engineering, Seoul National University, ENG 445, San 56-1, Shillim-dong, Kwanak-ku, Seoul 151-744 (Korea), Fax: (+82) 2-886-8331
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  • Soo Young Park Prof.

    1. Center for Supramolecular Optoelectronic Materials and WCU Hybrid Materials Program, Department of Materials Science and Engineering, Seoul National University, ENG 445, San 56-1, Shillim-dong, Kwanak-ku, Seoul 151-744 (Korea), Fax: (+82) 2-886-8331
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Abstract

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 π-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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