Abstract
ABSTRACTThe microwave synthesis of 12 rhodamine-derived imines is described. The present work involves condensation of rhodamine hydrazide with various aromatic aldehydes in ethanol under microwave irradiation. The results obtained indicate that, unlike classical heating, microwave irradiation results in higher yields, shorter reaction time, mild reaction condition and simple work-up procedure. The structures of synthesized compounds were confirmed by 1H-NMR, 13C-NMR, FT-IR and high-resolution mass spectra data.
Highlights
IntroductionIt has been known for many years that the rhodamine compounds are widely used class of dyes due to their versatile applications in various fields [1, 2]
We present an efficient, clean and straightforward procedure to prepare a series of rhodamine-derived imine compounds by Microwave-assisted organic synthesis (MAOS) under minimum solvent conditions, with short reaction times, and using ethanol as a green solvent to obtain the rhodamine derivatives from crude reaction mixtures without the use of complicated work-up
Rhodamine B hydrazide was synthesized from the parent rhodamine B and hydrazine in the one-step process described above using microwave irradiation and conventional oil-bath heating, by adopting the procedure reported in the literature [22]
Summary
It has been known for many years that the rhodamine compounds are widely used class of dyes due to their versatile applications in various fields [1, 2]. Rhodamine dyes see the widespread application as fluorescent sensors. Because of their strong fluorescence and good photostability, rhodamine derivatives have been found to have applications in laser active media [3], fluorescent markers in biology [4], imaging and bioanalysis [5], DNA sequencing [6] and fluorescence switchers and sensors [7–10]. Rhodamine-based compounds have properties, such as very high molar extinction coefficients and high fluorescent quantum yields, ideal for use as chemical sensors [11]. A strong effort has been focused on the design of ‘turn-on’ sensors, in which non-fluorescent molecules are activated in the presence of cations. Cations can trigger the change in structure between the spirocyclic and open-cycle form and rhodamine-based compounds have been well established as sensors for metal ions such as Cu2+(12, 13), Fe3+
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