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Issue 25, 2017
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Dual fluorescent zwitterionic organogels of a quinoxalinone derivative using cation–anion detection keys

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Abstract

An [18]crown-6 unit was introduced into a cation–anion dual-ion-sensing quinoxalinone derivative (1) as a new fluorescent molecule for successive cation (K+) and anion (F and CH3COO) sensing in CH3CN. High anion-sensing abilities for F and AcO were observed at the hydrogen-bonded acidic N–H proton of the positively charged K+-capturing 1 at the [18]crown-6 site due to electrostatic cation–anion interactions. On the other hand, the acidic N–H proton of lactam tautomer 1 strongly recognized basic AcO or F anions via N–H⋯AcO or F hydrogen-bonding interactions, and further AcO or F additions facilitated the deprotonation reaction, forming anionic 1. Anionic 1 showed a much higher K+-sensing ability at the [18]crown-6 site than neutral 1 through effective cation–anion electrostatic interactions. Interestingly, the electrostatically stabilized zwitterionic K+·1 formed fluorescent organogels in CH3CN, acetone, and THF; the organogels underwent reversible transformation between a blue fluorescent organogel and green fluorescent sol by the addition of trifluoroacetic acid (gel → sol) and trimethylamine (sol → gel). Both K+ and AcO (or F) ions acted as the key ions in the fluorescent organogel formation.

Graphical abstract: Dual fluorescent zwitterionic organogels of a quinoxalinone derivative using cation–anion detection keys

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Publication details

The article was received on 24 Mar 2017, accepted on 17 May 2017 and first published on 07 Jun 2017


Article type: Paper
DOI: 10.1039/C7TC01242J
Citation: J. Mater. Chem. C, 2017,5, 6234-6242
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    Dual fluorescent zwitterionic organogels of a quinoxalinone derivative using cation–anion detection keys

    Y. Nakane, T. Takeda, N. Hoshino, K. Sakai and T. Akutagawa, J. Mater. Chem. C, 2017, 5, 6234
    DOI: 10.1039/C7TC01242J

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