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Issue 38, 2018
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Dual fluorescence switching of a Rhodamine 6G-naphthalimide conjugate with high contrast in the solid state

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Abstract

Solid-state fluorescence switches have attracted tremendous attention in recent years owing to their applications in fluorescent sensors, security inks and data storage. Herein, we report a novel molecule (2NR) composed of two naphthalimide moieties and a Rhodamine 6G (R6G) unit linked by a branched amidoamine spacer. 2NR exhibits excellent acid and force dual-stimuli-responsive behaviour in the solid state: (i) exposing 2NR powder to HCl vapour results in fluorescence off–on switching, because protonation of the tertiary amine by acid impedes the photoinduced electron transfer process; (ii) further treatment with grinding, the force-induced open-ring reaction of R6G and subsequent efficient fluorescence resonance energy transfer from naphthalimide to the open-ring form of R6G realizes a high-contrast fluorescent colour change. Moreover, the branched amidoamine spacer induces a twisted conformation of naphthalene moieties, which provides considerable free volume and significantly facilitates the isomerization process of R6G from spirolactam to open-ring amide. Both fluorescence switches have good reversibility. Consequently, the excellent solid-state fluorescent switching of 2NR is highly applicable for anti-counterfeiting materials.

Graphical abstract: Dual fluorescence switching of a Rhodamine 6G-naphthalimide conjugate with high contrast in the solid state

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Publication details

The article was received on 24 Jul 2018, accepted on 25 Aug 2018 and first published on 28 Aug 2018


Article type: Paper
DOI: 10.1039/C8TC03654C
J. Mater. Chem. C, 2018,6, 10270-10275

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    Dual fluorescence switching of a Rhodamine 6G-naphthalimide conjugate with high contrast in the solid state

    L. Tan, S. Mo, B. Fang, W. Cheng and M. Yin, J. Mater. Chem. C, 2018, 6, 10270
    DOI: 10.1039/C8TC03654C

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