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Issue 10, 2016
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Microwave-assisted synthesis and photophysical studies of novel fluorescent N-acylhydrazone and semicarbazone-7-OH-coumarin dyes

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Abstract

A microwave-assisted synthesis of novel N-acylhydrazone and semicacarbazone-7-hidroxy-coumarins derivatives, starting from 3-acetyl-7-hydroxy-2H-chromen-2-one, is described. This optimized protocol led to higher yields and considerable reduction in reaction time from ∼24 to ∼1 hour. Aqueous solutions of these compounds showed bright blue to cyan emission and maximum quantum yields of 0.244. The stereoelectronic effects of the attached groups led to modulation of the spectral characteristics by favoring syn or anti amide conformers. The synthesized compounds showed pH dependent luminescence and a strong batochromic shift up to 65 nm in a low polarity medium (methanol) due to a better stabilization of the syn-conformer promoting this redshifted emission. These characteristics can be exploited for designing new luminescent probes for pH as well as polar microenvironments.

Graphical abstract: Microwave-assisted synthesis and photophysical studies of novel fluorescent N-acylhydrazone and semicarbazone-7-OH-coumarin dyes

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Supplementary files

Article information


Submitted
15 May 2016
Accepted
31 Aug 2016
First published
01 Sep 2016

New J. Chem., 2016,40, 8846-8854
Article type
Paper

Microwave-assisted synthesis and photophysical studies of novel fluorescent N-acylhydrazone and semicarbazone-7-OH-coumarin dyes

T. M. Pereira, F. Vitório, R. C. Amaral, K. P. S. Zanoni, N. Y. Murakami Iha and A. E. Kümmerle, New J. Chem., 2016, 40, 8846
DOI: 10.1039/C6NJ01532H

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