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Synthesis, Photophysical, Electrochemical and Thermal Studies of Triarylamines based on benzo[g]quinoxalines

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Abstract

A series of novel dipolar and nonplanar compounds featuring electron acceptor benzo[g]quinoxaline and various electron donor triarylamine units have been synthesized in good yields and fully characterized. The photophysical, electrochemical and thermal properties of the synthesized compounds are described. The photoluminescence properties of the synthesized molecules are influenced by peripheral amines. The derivatives have high Stokes shifts, low band gap and the Commission Internationale de l’Eclairage (CIE) coordinates are positioned in the green–yellow region of the chromaticity diagram. The ionization potentials and electron affinity were found to be in the range of 5.11–5.60 eV and 2.77–2.93 eV and are comparable to the commonly used hole transporters. Thermal studies also reveal that these synthesized molecules have good thermal stability with 5% and 10% weight loss temperature ranging from 200 to 355°C and 268 to 442°C, respectively.

The absorption, emission, electrochemical and thermal properties of the synthesized materials is significantly influenced by the nature of peripheral amine segments attached to the benzo[g]quinoxaline segment. Ionization potential and electron affinity of the synthesized molecules are comparable to most commonly used hole transporting materials with good thermal stability.

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Acknowledgements

The authors are greatly thankful to Micro-Analytical Laboratory, Department of Chemistry, and University of Mumbai for providing Instrumental facilities. One of the authors (Azam M. Shaikh) is grateful to University Grants Commission, India for providing Junior Research Fellowship.

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Authors and Affiliations

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

    AZAM M SHAIKH, BHARAT K SHARMA & RAJESH M KAMBLE

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

Additional information

Supplementary Information

All additional information pertaining to compounds 2–6, namely, absorption and emission spectra in CH2Cl2, CHCl3 and solid thin films (figures S1 and S2), Chromaticity diagrams (figures S3), Cyclic voltammograms (cathodic sweep) (figures S4 and S5), DTA plot (figure S6), HRMS spectra (figure S7), FTIR spectra (figure S8), 1H and 13C NMR spectra (figures S9 and S10), Photographs (figures S11 and S12) are given in the supporting information. Supplementary Information is available at www.ias.ac.in/chemsci.

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SHAIKH, A.M., SHARMA, B.K. & KAMBLE, R.M. Synthesis, Photophysical, Electrochemical and Thermal Studies of Triarylamines based on benzo[g]quinoxalines. J Chem Sci 127, 1571–1579 (2015). https://doi.org/10.1007/s12039-015-0904-0

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  • DOI: https://doi.org/10.1007/s12039-015-0904-0

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