Naphthalimide modified rhodamine B derivative as well as preparation method and application thereof

Abstract

The invention relates to detection of metal ions through a fluorescence method, and in particular relates to a naphthalimide modified rhodamine B derivative 1 for identifying copper ions (II) based on a fluorescence resonance energy transfer (FRET) mechanism. The derivative 1 has a structure shown by a formula (1). The preparation method of the derivative 1 comprises the steps of enabling N-butyl-4-bromo-1,8-naphthalimide to react with hydrazine hydrate to synthesize an intermediate compound a; enabling a rhodamine B hydrazinolysis product to react with glyoxal to synthesize an intermediate compound b; then performing a reflux reaction for 4 hours between the two intermediate compounds in a mole ratio of 1:1 in an ethanol solution under a reflux condition, cooling, performing suction filtration on an obtained solid, and performing ethanol recrystallization to obtain a yellow solid. The naphthalimide modified rhodamine B derivative 1 can be used as a fluorescent probe to realize identification detection of copper ions based on the FRET mechanism. According to the invention, the rhodamine B derivative 1 is obtained through an effective synthetic method, is good in selectivity to copper ions and can realize detection of copper ions on the basis of optimized experimental conditions.

Description

technical field [0001] The invention relates to a fluorescent probe, specifically a naphthalimide-modified rhodamine B derivative and its preparation and application. Background technique [0002] Fluorescent probe method has been widely used in the detection of target substances. Among the reported fluorescent molecular probes, most of them have the following disadvantages: complex synthesis and separation, large interference of other coexisting ions in the test process, high detection limit, and quenching response signals, etc. (Y.T.Li and C.M.Yang, Chem. Commun., 2003, 2884-2885.L; Fabbrizzi, M.Licchelli, P.Pallavicini, A.Perotti, A.Taglietti and D.Sacchi, Chem.Eur.J., 1996; 75-82.M.N.Elizabeth, J.L. Stephen, J. Mater. Chem., 2005, 15, 2778--2783.) These have brought great influence and inconvenience to the detection of metal ions. [0003] Numerous mechanisms based on fluorescence detection have been continuously reported, among which the FRET mechanism has certain adv...

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Problems solved by technology

Among the reported fluorescent molecular probes, most of them have the following disadvantages: complex synthesis and separation, large interference of other coexisting ions in the test process, high detection limit, and quenching response signals, etc. (Y.T.Li and C.M.Yang, Chem. Commun., 2003, 2884-2885.L; Fabbrizzi, M.Licchelli, P.Pallavicini, A.Perotti, A.Taglietti and D.Sacchi, Chem.Eur.J., 1996; 75-82.M.N.Elizabeth, J.L. Stephen, J.Mater.Chem., 2005, 15, 2778-–2783.) These have brought great influence and inconvenience to the detection of metal ions

Fluorescent probes based on these two luminophores have been successfully used for the detection of mercury ions and chromium ions, but no fluorescent probes for the detection of copper ions have been developed and reported.

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