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Photophysical and Electrochemical Properties of Highly π-Conjugated Bipolar Carbazole-1,3,4-Oxadiazole-based D-π-A Type of Efficient Deep Blue Fluorescent Dye

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Abstract

In this contribution, we have designed and synthesized a novel carbazole-1,3,4-oxadiazole based bipolar fluorophore (E)-2-(4-(4-(9H-carbazol-9-yl)styryl)phenyl)-5-(4-(tertbutyl) phenyl)-1,3,4-oxadiazole (CBZ-OXA-IV). Wittig reaction is utilised for the synthesis of the designed bipolar target compound CBZ-OXA-IV. 1H NMR, 13C NMR, FT-IR and ESI–MS results confirmed the designed chemical structure of the fluorophore CBZ-OXA-IV. The photophysical properties have been investigated in detail using UV–Vis absorption, photoluminescence spectroscopy. Also, the photoluminescence studies on solid state samples (as thin films) were carried out. The CBZ-OXA-IV dye emits intense deep blue fluorescence with observed absorption and emission maxima occurring are at 353 nm and 470 nm, respectively. Fluorophore CBZ-OXA-IV has shown high Stokes shift of 7052 cm−1. The experimentally measured optical band gap (\({E}_{g}^{opt}\)) value is found to be 3.01 eV and the fluorescence quantum yields (Φf) is 0.40. The intramolecular charge transfer property of CBZ-OXA-IV dye was examined by using photophysical properties such as absorption, emission in different solvents of different varying polarities. In addition, Density Functional Theory computations are studied in detail including the MEP surface plots and natural bond orbital analysis. The electrochemical properties have been investigated in detail by using cyclic voltammetry measurements. Thermal gravimetric analysis (TGA) and differential scanning calorimetry (DSC) measurement results display a high thermal stability with decomposition temperature (Td5%) 387 °C and a large glass transition temperature (Tg) of 98 °C. The obtained results demonstrated that the novel bipolar fluorophore CBZ-OXA-IV could play an important role in organic optoelectronics and possibly can be utilized as bipolar transport materials for electroluminescence applications in optoelectronic devices/OLEDs.

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Acknowledgements

We are thankful to the University Scientific Instrument Centre (USIC) and SAIF, Karnatak University, Dharwad for providing the spectral data. Also to the University Grants Commission (UGC), New Delhi, India, for providing financial support under UGC-SRF (Sr. No. 2121510180 Ref. No. 20/12/2015) and DST-Purse Phase-II program for providing necessary facilities. The authors, Tilakraj T S is thankful to UGC-JRF for funding (Sr. No. 2061651259 Dated. 26/10/2017) and Mallikarjun K. Patil would like to thank KSTePS Govt. of Karnataka for Providing DST-Ph.D fellowship.

Funding

No specific funding was received for this project. Mahesh Sadashivappa Najare is supported by a University Grants Commission (UGC), New Delhi, India, under UGC-SRF (Sr. No. 2121510180 Ref. No. 20/12/2015). All authors confirm their work is independent from the funders.

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Authors and Affiliations

  1. Department of Chemistry, Karnatak University, Dharwad, 580003, Karnataka, India

    Mahesh Sadashivappa Najare, Mohammed Yaseen,  AfraQuasar A Nadaf, Shivaraj Mantur & Imtiyaz Ahmed M Khazi

  2. Laser Spectroscopy Programme, Department of Physics, UGC-CPEPA, Karnatak University, Dharwad, 580003, Karnataka, India

    Mallikarjun Kalagouda Patil, Tarimakki Shankar Tilakraj & Sanjeev Ramchandra Inamdar

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  1. Mahesh Sadashivappa Najare
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Contributions

Mahesh S. Najare: Conceptualization, design of study and Writing-Original draft preparation. Mallikarjun K. Patil: Acquisition of data and Writing-Original draft preparation. Tilakraj T S: Analysis, interpretation of data and Formal analysis. Mohammed Yaseen: Resources and Software. AfraQuasar A. Nadaf: Data Curation and Validation. Shivaraj Mantur: Analysis and interpretation of data. Sanjeev R. Inamdar: Visualization, Investigation, Reviewing and Editing. Imtiyaz Ahmed M. Khazi: Supervision.

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Najare, M.S., Patil, M.K., Tilakraj, T.S. et al. Photophysical and Electrochemical Properties of Highly π-Conjugated Bipolar Carbazole-1,3,4-Oxadiazole-based D-π-A Type of Efficient Deep Blue Fluorescent Dye. J Fluoresc 31, 1645–1664 (2021). https://doi.org/10.1007/s10895-021-02778-1

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