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4,5-Diaminophthalimides: highly efficient solid-state fluorophores and turn-on type fluorescent probes for hydrazine

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Abstract

We report herein that 4,5-bis(diarylamino)phthalimides exhibit efficient solid-state emission. The phthalimides were easily prepared from dimethyl 4,5-bis(diarylamino)phthalates or commercially available 4,5-dichlorophthalic acid via a few steps. The absorption spectra of the phthalimides in toluene showed strong bands at 337–374 nm and weak bands possessing two shoulders at 378–455 nm. Toluene solutions of the phthalimides fluoresced in the greenish blue to orange-yellow region with good-to-high quantum yields. In contrast, the phthalimides showed no emission in DMSO. Based on the observation, phthalimide was demonstrated to serve as a turn-on type fluorescent probe for hydrazine. The phthalimides dispersed in a thin film of poly(methyl methacrylate) and in powder form fluoresced in the blue-to-green and green-to-orange region, respectively, with high quantum yields. As the electron-donating ability of the diarylamino moieties increased, the emission spectra in solution and the solid states were red-shifted. The density functional theory calculations confirm that the photo-excitation involves an intramolecular charge transfer from diarylamino groups to imide-carbonyl moieties.

Graphical abstract: 4,5-Diaminophthalimides: highly efficient solid-state fluorophores and turn-on type fluorescent probes for hydrazine

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Publication details

The article was received on 13 Nov 2018, accepted on 18 Dec 2018 and first published on 19 Dec 2018


Article type: Research Article
DOI: 10.1039/C8QM00578H
Citation: Mater. Chem. Front., 2019, Advance Article
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    4,5-Diaminophthalimides: highly efficient solid-state fluorophores and turn-on type fluorescent probes for hydrazine

    M. Shimizu, T. Tamagawa and K. Nishimura, Mater. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QM00578H

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