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Novel BODIPY-Fluorene-Fullerene and BODIPY-Fluorene-BODIPY Conjugates: Synthesis, Characterization, Photophysical and Photochemical Properties

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Abstract

Two new BODIPY-fluorene-fullerene (3) and BODIPY-fluorene-BODIPY (4) conjugates were designed, synthesized, and characterized for the first time. The structural properties of compounds were investigated with elemental analysis, mass, 1H, and 13C NMR techniques. Absorption and fluorescence spectroscopy were used to examine the photophysical (absorption and emission profiles, fluorescence quantum yields, and lifetimes) and photochemical (formation of singlet oxygen (1O2)) properties. It was observed that the novel compounds (3) and (4) showed high molar extinction coefficients and good 1O2 quantum yields. 1O2 formation ability of the BODIPY-fluorene-fullerene conjugate (3) was more efficient than that of the BODIPY-fluorene-BODIPY conjugate (4). Furthermore, photosensitization ability of both conjugate systems was more remarkable than some commonly used BODIPY based photosensitizers. The data presented in this work indicate that these two novel systems are effective 1O2 photosensitizers that might be used for various areas of applications such as photodynamic therapy and photocatalysis.

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The datasets generated during and/or analysed during the current study are available in the supplementary file.

References

  1. Kue CS, Ng SY, Voon SH, Kamkaew A, Chung LY, Kiew LV, Lee HB (2018) Photochem Photobiol Sci 17:1691–1708

    Article  CAS  Google Scholar 

  2. Radunz S, Wedepohl S, Röhr M, Calderón M, Tschiche HR, Resch-Genger U (2020) J Med Chem 63:1699–1708

  3. Qi S, Kwon N, Yim Y, Nguyen V-N, Yoon J (2020) Chem Sci 11:6479–6484

  4. Zou J, Li L, Zhu J, Li X, Yang Z, Huang W, Chen X (2021) Adv Mater 33:2103627

    Article  CAS  Google Scholar 

  5. Loudet A, Burgess K (2007) Chem Rev 107:4891–4932

  6. Boens N, Verbelen B, Ortiz MJ, Jiao LJ, Dehaen W (2019) Coord Chem Rev 399

  7. Zhang J, Campbell RE, Ting AY, Tsien RY (2002) Nat Rev Mol Cell Bio 3:906–918

  8. Chan J, Dodani SC, Chang CJ (2021) Nat Chem 4:973–984

  9. Gao JH, Tao YF, Wang NN, He JL, Zhang J, Zhao WL (2018) Spectrochim Acta A 203:77–84

  10. Qin WW, Dou W, Leen V, Dehaen W, Van der Auweraer M, Boens N (2016) Rsc Adv 6:7806–7816

  11. Merkushev D, Vodyanova O, Telegin F, Melnikov P, Yashtulov N, Marfin Y (2022) Designs 6

  12. Marfin YS, Solomonov AV, Timin AS, Rumyantsev EV (2017) Curr Med Chem 24:2745–2772

  13. Ortiz MJ, Garcia-Moreno I, Agarrabeitia AR, Duran-Sampedro G, Costela A, Sastre R, Arbeloa FL, Prieto JB, Arbeloa IL (2010) PCCP 12:7804–7811

  14. Arbeloa FL, Banuelos J, Martinez V, Arbeloa T, Arbeloa IP (2005) Int Rev Phys Chem 24:339–374

  15. Singh SP, Gayathri T (2014) Eur J Org Chem 2014:4689–4707

  16. Turksoy A, Yildiz D, Akkaya EU (2019) Coord Chem Rev 379:47–64

  17. Yadav RK, Baeg JO, Kumar A, Kong KJ, Oh GH, Park NJ (2019) J Mater Chem A 2:5068–5076

  18. Yang H, Zhao M, Zhang J, Ma J, Wu P, Liu W, Wen L (2019) J Mater Chem A 7:20742–20749

  19. Huang L, Cui X, Therrien B, Zhao J (2013) Chemistry (Easton) 19:17472–17482

    CAS  Google Scholar 

  20. Wu WH, Zhao JZ, Sun JF, Guo S (2012) J Org Chem 77:5305–5312

    Article  CAS  Google Scholar 

  21. Yang P, Wu W, Zhao J, Huang D, Yi X (2011) J Mater Chem 22:20273–20283

  22. Huang L, Zhao J (2013) Chem Commun 49:3751–3753

  23. Ziessel R, Allen BD, Rewinska DB, Harriman A (2009) Chem A Eur J 15:7382–7393

  24. Chamberlain TW, Davies ES, Khlobystov AN, Champness NR (2011) Health Environ Res Online (HERO) 17:3759–3767

  25. Liu J-Y, El-Khouly ME, Fukuzumi S, Ng DK (2011) Chem Asian J 6:174–179

  26. Zhao H, Liao J, Peng M, Wang Y, Zhou W, Li B, Shen S, Xie Z (2015) Tetrahedron Lett 56(52):7145–7149

  27. Caporossi F, Floris B, Galloni P, Gatto E, Venanzi M, Mozzi AF, Urbani A, Kadish KM (2009) Synthetic Metals 159(14):1403–1408

  28. Zhang F, Zhang R, Liang XZ, Guo KP, Han ZX, Lu XQ, Xie JJ, Li J, Li D, Tian X (2018) Dyes Pigm 155:225–232

    Article  CAS  Google Scholar 

  29. Brouwer AM (2011) Pure Appl Chem 83:2213–2228

    Article  CAS  Google Scholar 

  30. Spiller W, Kliesch H, Wohrle D, Hackbarth S, Roder B, Schnurpfeil G, Porphyr J (1998) Phthalocyanines 2:145–158

    Article  CAS  Google Scholar 

  31. Ozturk E, Eserci H, Okutan E (2019) J Photochem Photobiol A 385

  32. Senkuytu E, Ecik ET (2017) Spectrochim Acta A 182:26–31

  33. Ecik ET, Senkuytu E, Cosut B (2017) Dyes Pigm 143:455–462

  34. Hu WB, Lin HY, Zhang XF, Feng MN, Zhao SW, Zhang J (2019) Dyes Pigm 164:139–147

  35. Filatov MA, Karuthedath S, Polestshuk PM, Callaghan S, Flanagan KJ, Wiesner T, Laquai F, Senge MO (2018) Chemphotochem 2:606–615

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Funding

The authors declare that no funds, grants, or other support were received during the preparation of this manuscript.

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Authors and Affiliations

  1. Department of Chemistry, Karabuk University, Karabuk, 78050, Turkey

    Semiha Yildirim Sarikaya

  2. Department of Chemistry, Gebze Technical University, Gebze, Kocaeli, 41400, Turkey

    Husniye Ardic Alidagi & Seda Cetindere

Authors
  1. Semiha Yildirim Sarikaya
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  2. Husniye Ardic Alidagi
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  3. Seda Cetindere
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Contributions

All authors contributed to the study conception and design. Material preparation, data collection and analysis were performed by Semiha Yildirim Sarikaya, Husniye Ardic Alidagi and Seda Cetindere. The first draft of the manuscript was written by all authors and all authors read and approved the final manuscript.

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Correspondence to Seda Cetindere.

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Sarikaya, S.Y., Alidagi, H.A. & Cetindere, S. Novel BODIPY-Fluorene-Fullerene and BODIPY-Fluorene-BODIPY Conjugates: Synthesis, Characterization, Photophysical and Photochemical Properties. J Fluoresc 33, 297–304 (2023). https://doi.org/10.1007/s10895-022-03060-8

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