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Fluorene-based conjugates with geminal donor-acceptor: synthesis, photophysical properties and theoretical studies

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Abstract

We report six new 2,6-disubstituted fluorene-based conjugated molecules carrying orthogonal triphenylamine and pyridine moiety as donor-acceptor units at the C-9 position. The geminal donor-acceptor is connected to the fluorene core by σ-conjugation. Optical/solvatochromic studies, investigated by UV-VIS absorption and fluorescence spectroscopy, show blue emission with good quantum yield (40–70%) in solution and in thin film state for the synthesized compounds. In microsecond order, the derivatives give a shorter delayed lifetime (both in solution and thin films), facilitating reverse intersystem crossing (RISC). TD-DFT studies for all the derivatives show minimal singlet-triplet splitting in the gas phase (close to 0.2 eV), and the high thermal stability confirmed by the compound's TGA method (320–398 °C) makes them very useful in the optoelectronic market.

Graphical abstract

D-σ-π-σ-A based blue emitters carrying orthogonal triphenylamine and pyridine moiety as donor-acceptor unit at C-9 position were synthesized. Optical/solvatochromic studies, investigated by UV-VIS absorption and fluorescence spectroscopy, show blue emission with good quantum yield (40–70%) in solution and in thin film state for the synthesized compounds.

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Acknowledgments

We are thankful to the Sophisticated Analytical Instrumental Facilities (SAIF), IIEST Shibpur, and India, for NMR & HRMS measurement & R.M. is thankful to the Indian Institute of Engineering Science and Technology, Shibpur, Howrah, India, for an Institute Fellowship.

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Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Engineering Science and Technology, Shibpur, Howrah, 711 103, India

    Riya Majumder & Binay K Ghorai

  2. Department of Chemistry, Ramakrishna Mission Vivekananda Centenary College, Kolkata, 700 118, India

    Debabrata Jana

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  1. Riya Majumder
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Correspondence to Binay K Ghorai.

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Majumder, R., Jana, D. & Ghorai, B.K. Fluorene-based conjugates with geminal donor-acceptor: synthesis, photophysical properties and theoretical studies. J Chem Sci 136, 20 (2024). https://doi.org/10.1007/s12039-024-02249-7

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