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One-Pot Synthesis, Spectroscopic and Physicochemical Studies of Quinoline Based Blue Emitting Donor—Acceptor Chromophores with Their Biological Application

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Abstract

Blue emitting cyano substituted isoquinoline dyes were synthesized by one-pot multicomponent reactions (MCRs) of aldehydes, malononitrile, 6-methoxy-1,2,3,4-tetrahydro-naphthalin-1-one and ammonium acetate. Results obtained from spectroscopic (FT-IR, 1H-NMR, 13C-NMR, EI-MS) and elemental analysis of synthesized compounds was in good agreement with their chemical structures. UV–vis and fluorescence spectroscopy measurements proved that all compounds are good absorbent and fluorescent. Fluorescence polarity study demonstrated that these compounds were sensitive to the polarity of the microenvironment provided by different solvents. In addition, spectroscopic and physicochemical parameters, including electronic absorption, excitation coefficient, stokes shift, oscillator strength, transition dipole moment and fluorescence quantum yield were investigated in order to explore the analytical potential of synthesized compounds. The anti-bacterial activity of these compounds were first studied in vitro by the disk diffusion assay against two Gram-positive and two Gram-negative bacteria then the minimum inhibitory concentration (MIC) was determined with the reference of standard drug chloramphenicol. The results displayed that compound 3 was better inhibitors of both types of the bacteria (Gram-positive and Gram-negative) than chloramphenicol.

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Acknowledgments

This Project was funded by the King Abdulaziz City for Science and Technology (KACST) through National Science, Technology and Innovation Plan (NSTIP) under grant number 8-ENE198-3. The authors, therefore, acknowledge with thanks KACST for support for Scientific Research. Also, the authors are thankful to the Deanship of Scientific Research (DSR), King Abdulaziz University for their technical support.

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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

    Abdullah M. Asiri, Salman A. Khan & Saad H. Al-Thaqafya

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

    Abdullah M. Asiri

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  1. Abdullah M. Asiri
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  2. Salman A. Khan
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  3. Saad H. Al-Thaqafya
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Correspondence to Salman A. Khan.

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Asiri, A.M., Khan, S.A. & Al-Thaqafya, S.H. One-Pot Synthesis, Spectroscopic and Physicochemical Studies of Quinoline Based Blue Emitting Donor—Acceptor Chromophores with Their Biological Application. J Fluoresc 25, 1203–1213 (2015). https://doi.org/10.1007/s10895-015-1607-0

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