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Green-synthesis, characterization, photostability and polarity studies of novel schiff base dyes using spectroscopic methods

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Abstract

Preparation, characterization, photostability and polarity studies of novel Schiff base dyes using spectroscopic methods were achieved. The Schiff base dyes were prepared by the reaction of salicylalde-hyde/2-hydroxy-l-naphthaldehyde with aminophenazone under microwave irradiation. The spectroscopic (FT-IR, 1H NMR, 13C NMR, Mass) studies and elemental analyses were in good agreement with chemical structure of synthesized compounds. In addition, UV-Vis and fluorescence spectroscopic experiments showed that these dyes are good absorbent and fluorescent. Based on the photostability study of these dyes, minimal to no loss in fluorescence intensities of 4-[(2-hydroxy-benzylidene)-amino]1,5-dimemyl-2-phe-nyl-1,2-dihydro-pyrazol-3-one (D1) (6.14%) and 4-[(2-hydroxy-naphthalen-l-ylmethylene)-amino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one (D2) (2.95%) was observed with an increase in the exposure time using time-based fluorescence steady-state experiments. These studies also inferred that these Schiff base dyes have a high photostability against photobleaching. In addition, Dye 2 is found to be more sensitive than Dye 1 to the polarity of the microenvironment provided by different solvents based on the results of fluorescence polarity studies.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah, 21589, Saudi Arabia

    Hadi M. Marwani, Abdullah M. Asiri & Salman A. Khan

  2. Center of Excellence for Advanced Materials Research, King Abdulaziz University, P.O. Box 80203, Jeddah, 21589, Saudi Arabia

    Hadi M. Marwani & Abdullah M. Asiri

Authors
  1. Hadi M. Marwani
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  2. Abdullah M. Asiri
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  3. Salman A. Khan
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Correspondence to Salman A. Khan.

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Marwani, H.M., Asiri, A.M. & Khan, S.A. Green-synthesis, characterization, photostability and polarity studies of novel schiff base dyes using spectroscopic methods. Russ J Bioorg Chem 38, 533–538 (2012). https://doi.org/10.1134/S1068162012050056

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  • DOI: https://doi.org/10.1134/S1068162012050056

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