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Synthesis and photophysical properties of pyridyl conjugated triazole appended naphthalenediimide derivatives

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Abstract

A series of three substituted triazole appended NDI-derivatives, 2,7-bis(3,5-di(pyridin-X-yl)-4H-1,2,4-triazol-4-yl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone (where X = 2, NDI-PyTz-1; 3, NDI-PyTz-2; and 4, NDI-PyTz-3), were designed, synthesized and well characterized using various analytical and spectroscopic techniques. All the three NDI-PyTz derivatives exhibit decent electronic properties as suggested by DFT, cyclic voltammetry and fluorescence studies. In particular, NDI-PyTz-1 demonstrated the generation of a stable anion radical [NDI-PyTz-1]•−.

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Acknowledgements

G. Kumar thanks the Department of Science and Technology (DST), Government of India for the financial assistance in the form of the INSPIRE Faculty Award with Ref. No. [DST/ INSPIRE/04/2015/001300]. The authors are grateful to the UGC networking resource centre, School of Chemistry, University of Hyderabad, Hyderabad for providing the NMR, CHN, single crystal X-ray diffraction and XRD powder facilities. Dr Praveen Kumar, Department of Physics, DAV University, Jalandhar is gratefully acknowledged for providing the support for fluorescence studies. We thank Dr Mohd Afzal, Department of Chemistry, Jadavpur University, Kolkata for valuable discussions and help with the fluorescence data.

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  1. Department of Chemistry & Centre for Advanced Studies in Chemistry, Panjab University, Chandigarh, 160014, India

    Girijesh Kumar, Ranjan Patra &  Kirandeep

  2. Department of Chemistry, Kakatiya University, Warangal, 506009, India

    Ramu Guda & Mamatha Kasula

  3. Department of Chemistry, DAV University Jalandhar, Punjab, 144012, India

    Ahmad Husain

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  1. Girijesh Kumar
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Correspondence to Girijesh Kumar.

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Kumar, G., Guda, R., Husain, A. et al. Synthesis and photophysical properties of pyridyl conjugated triazole appended naphthalenediimide derivatives. Photochem Photobiol Sci 18, 1333–1341 (2019). https://doi.org/10.1039/c9pp00003h

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