Cd2+-selective fluorescence response of TQEN (N,N,N′,N′-tetrakis(2-quinolylmethyl)ethylenediamine) derivatives bearing ether oxygen-binding sites?

Dalton Transactions Pub Date: 2022-10-17 DOI: 10.1039/D2DT02948K

Abstract

Moderate Zn2+ selectivity over Cd2+ (IZn/ICd = 1.6) in the fluorescence enhancement of TQEN (N,N,N′,N′-tetrakis(2-quinolylmethyl)ethylenediamine) was changed to Cd2+ preference via the introduction of a methoxymethyloxy (MOMO) substituent at the 8-position of one of the four quinoline rings (IZn/ICd = 0.2). Thus, 8-MOMOTQEN (N-(8-methoxymethyloxy-2-quinolylmethyl)-N,N′,N′-tris(2-quinolylmethyl)ethylenediamine) showed not only high Cd2+-selectivity but also an enhanced fluorescence quantum yield upon Cd2+ binding and high sensitivity for Cd2+ detection as shown by ?Cd = 0.065 and LOD (limit of detection) = 19 nM. The two oxygen atoms of the MOMO group in 8-MOMOTQEN play a crucial role in the fluorescent metal-ion selectivity because the corresponding hydroxy (8-OHTQEN) and methoxy (8-MeOTQEN) derivatives resulted in a poor fluorescent response and metal selectivity, respectively. Another N6O2 ligand, N,N′-bis(8-methoxy-2-quinolylethyl)-N,N′-bis(2-quinolylmethyl)ethylenediamine ((8-MeO)2TQEN) exhibited a Zn2+-selective fluorescence enhancement (IZn/ICd = 2.2), indicating the superiority of the MOMO group for the selective sensing of Cd2+.

Graphical abstract: Cd2+-selective fluorescence response of TQEN (N,N,N′,N′-tetrakis(2-quinolylmethyl)ethylenediamine) derivatives bearing ether oxygen-binding sites
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