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Synthesis, photophysical, electrochemical and thermal investigation of Triarylamines based on 9H-Xanthen-9-one: Yellow–green fluorescent materials

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Abstract

Triarylamines containing 9 H−Xanthen −9−one core and aromatic units such as phenyl, naphthyl and p −methoxyphenyl were synthesized by employing palladium catalyzed C −N bond forming amination reaction in good yields. The photophysical studies revealed that the absorption and emission spectra are influenced by the nature of the peripheral amines. The photoemission spectra can be readily tuned in the range 483–532 nm (solution) and 525–576 nm (film) displaying green or yellow emission (film) depending on the nature of the amine segment with optical band gaps in the range 2.52–2.75 eV (film). The ionization potential and electron affinity were found to be in the range 5.332–5.686 eV and 2.705–2.776 eV, respectively. Thermal studies revealed that the synthesized compounds have good thermal stability with 5% and 10% weight loss at temperature ranging from 260–330∘C and 340–370∘C, respectively.

The triarylamines containing 9H-Xanthen-9-one were synthesized via palladium-catalyzed C−N bond forming reaction in good yields. The absorption, emission, electrochemical and thermal properties of the dyes were studied and found to be significantly influenced by the nature of the peripheral amine segments attached to the xanthone core.

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Acknowledgments

We thank the Micro-Analytical Laboratory, Department of Chemistry, University of Mumbai for providing Instrumentation facility. We also thank the Department of Chemistry IIT-Mumbai for providing HR-MS Spectra.

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Authors and Affiliations

  1. Department of Chemistry, University of Mumbai, Santacruz (East), Mumbai, 400 098, India

    BHARAT K SHARMA, AZAM M SHAIKH & RAJESH M KAMBLE

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  1. BHARAT K SHARMA
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  2. AZAM M SHAIKH
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Correspondence to RAJESH M KAMBLE.

Additional information

Supplementary Information

All the additional details pertaining to the characterization of the compounds 2–4 using FT-IR (figures S1), 1H NMR (figure S2), 13C NMR (figure S3), HRMS spectra (figure S4), UV-Vis absorption and emission spectra (figure S5), Absorption and Emission Properties of compound 2–4 in solvents of varying polarity and their CIE Coordinates as thin solid film (table S1), Emission and Excitation Spectra (figure S7), complete scan Cyclic Voltammograms (figure S8), Derivative weight loss and DTA plots (figure S9), CIE coordinates (figure S10) and Photograph of compounds in solution form (figure S11) are given in the Supporting Information. Supplementary Information is available at www.ias.ac.in/chemsci.

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SHARMA, B.K., SHAIKH, A.M. & KAMBLE, R.M. Synthesis, photophysical, electrochemical and thermal investigation of Triarylamines based on 9H-Xanthen-9-one: Yellow–green fluorescent materials. J Chem Sci 127, 2063–2071 (2015). https://doi.org/10.1007/s12039-015-0973-0

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  • DOI: https://doi.org/10.1007/s12039-015-0973-0

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