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Issue 18, 2018
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Water-soluble naphthalene diimides: synthesis, optical properties, and colorimetric detection of biogenic amines

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Abstract

A large number of water-soluble naphthalene diimides (NDIs) bearing an electron-withdrawing chloro and electron-donating amino-substituents with varied electronic character at the core were synthesized by a two-step synthetic approach comprising imidization of 2,6-dichloronaphthalene dianhydride with L-glutamic acid or 2-dimethylaminoethylamine and subsequent nucleophilic substitution of a chlorine atom with primary amines. These new donor–acceptor NDI dyes show absorption and emission maxima beyond 500 nm and fluorescence quantum yields up to 39% in aqueous phosphate buffer solution at acidic and neutral pH values. Our studies revealed a significant effect of core amino-substituents on the optical properties of these NDIs. With increasing electron-withdrawing character of the residues of amino-substituents the absorption and emission maxima are more hypsochromically shifted and the fluorescence quantum yields are markedly increased with the highest value of 39% for NDIs containing a strongly electron withdrawing trifluroethyl group in the amino-substituent. Furthermore, the high reactivity of the core-dichlorinated NDI dye could be utilized for the optical detection of primary amines and biogenic diamines putrescine and cadaverine.

Graphical abstract: Water-soluble naphthalene diimides: synthesis, optical properties, and colorimetric detection of biogenic amines

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Publication details

The article was received on 22 Jun 2018, accepted on 03 Aug 2018 and first published on 10 Aug 2018


Article type: Research Article
DOI: 10.1039/C8QO00611C
Citation: Org. Chem. Front., 2018,5, 2641-2651
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    Water-soluble naphthalene diimides: synthesis, optical properties, and colorimetric detection of biogenic amines

    A. Weißenstein, V. Grande, C. R. Saha-Möller and F. Würthner, Org. Chem. Front., 2018, 5, 2641
    DOI: 10.1039/C8QO00611C

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