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Selective Fluorimetric Detection of Primary Alkylamines by a Calix[6]arene Funnel Complex

Remy, C; Guyon, H; Rebilly, J-N; Leray, I; Reinaud, O, Chemistry-A European Journal, 2017, 23, 8669-8677.

The association of host–guest and coordination chemistry was used to develop a fluorescent molecular sensor. A calix[6]arene bearing three imidazole arms at the small rim and three quinoline fluorophores at the large rim was synthesized and characterized. A two‐step coordination sequence was observed upon addition of ZnII. The first ZnII center binds the tris‐imidazole small rim site, leading only to a small perturbation of the fluorescence. In contrast, a large bathochromic shift is observed upon binding of the second ZnII center at the large rim as a result of the direct interaction of ZnII with the quinoline fluorophores. The system acts as a selective receptor for primary amines. Host–guest adduct formation could be identified by a shift and enhancement of the fluorescence emission that is dependent on the length and shape of the primary amine. This system constitutes a fluorescent reporter with a selective response among primary amines.

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Publication

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Paru le 27 juin 2017

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DOI: 10.1002/chem.201700640