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Synthesis and Photophysical Properties of Fluorescein Esters as Potential Organic Semiconductor Materials

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Abstract

Fluorescein (1), a known fluorescent tracer in microscopy with high photophysical properties, was esterified to have fluorescein ethyl ester (2) and O-ethyl-fluorescein ethyl ester (3) in excellent yields. All of them were investigated for the photophysical and electrochemical properties as potential organic semiconductor materials. Absorptions and emission spectra were taken in various solvents, compound 2 showed emission maxima at λmax = 545 and compound 3 showed λmax = 550 nm. Optical band gap energy (Eg) was calculated for 1–3 and the values were found in between 2.34 – 2.39 eV. Possibility of shifting emission maxima was studied in various pH (5–9) buffers, and finally the thermal stability was examined using differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). Increasing of conjugation system of 2 and 3 were studied by HOMO and LUMO distributions of 1–3. Experimental results showed that compounds 2 and 3 have excellent photophysical and electrochemical properties hence can be used as excellent organic semiconductor materials.

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Unreported NMR, IR and Mass spectra for compounds 1–3 are given in supporting information files, samples and all other data and materials from this manuscript will be made available on request.

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Acknowledgements

The authors extend their appreciation to the Deanship of Scientific Research at King Saud University for funding the work through the research group project No. RG-1436-024.

Funding

This research was funded by the Deanship of Scientific Research at King Saud University for funding the work through the research group project No. RG-1436–024.

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh, 11451, Saudi Arabia

    Gamal A. E. Mostafa, Haitham AlRabiah, Adnan A. Kadi & A. F. M. Motiur Rahman

  2. Micro-Analytical Laboratory, Department of Applied Organic Chemistry, National Research Center, Dokki, 12622, Cairo, Egypt

    Gamal A. E. Mostafa

  3. Department of Electronic and Electrical Engineering, Southwest Jiaotong University (SWJTU), University of Leeds UK Joint School, XIPU Campus, Chengdu, China

    Abu Syed Mahajumi

  4. Institute of Drug Discovery Technology, Ningbo University, Ningbo, China

    Yang Lu

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  3. Haitham AlRabiah
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  4. Adnan A. Kadi
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Contributions

G.A.E. Mostafa performed absorbance and fluorescence measurements; A.S. Mahajumi checked the literature, wrote the part of manuscript, H. AlRabiah and A.A. Kadi provided the equipment’s and laboratory facilities, revised the manuscript; Y. Lu performed HOMO–LUMO calculation and wrote the part of manuscript; A.F.M.M. Rahman conceived the research thought, designed the experimental scheme, edited the manuscript.

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Mostafa, G.A.E., Mahajumi, A.S., AlRabiah, H. et al. Synthesis and Photophysical Properties of Fluorescein Esters as Potential Organic Semiconductor Materials. J Fluoresc 31, 1489–1502 (2021). https://doi.org/10.1007/s10895-021-02789-y

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