Research Article
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Year 2025, Volume: 21 Issue: 3, 35 - 42, 26.09.2025
https://doi.org/10.18466/cbayarfbe.1582319

Abstract

Project Number

KBÜBAP-24-DS-103

References

  • [1]. Dai, Y, Sun, J, Zhang, X, Zhao, J, Yang, W, Zhou, J, Gao, Z, Wang, Q, Yu, F, Wang, B. 2024. Supramolecular assembly boosting the phototherapy performances of BODIPYs. Coordination Chemistry Reviews; 517: 216054.
  • [2]. Yilmaz, RF, Derin, Y, Misir, BA, Atalay, VE, Tutar, ÖF, Ökten, S, Tutar, A. 2023. Synthesis and spectral properties of symmetrically arylated BODIPY dyes: Experimental and computational approach. Journal of Molecular Structure; 1291: 135962.
  • [3]. Joshi, DK, Betancourt, F, Pilkington, M, Yan, H. 2023. Neutral BODIPY derivatives as photosensitizers. Journal of Photochemistry and Photobiology A: Chemistry; 442: 114770.
  • [4]. Gündüz, EÖ, Gedik, ME, Günaydın, G, Okutan, E. 2022. Amphiphilic Fullerene-BODIPY Photosensitizers for Targeted Photodynamic Therapy. ChemMedChem; 17 (6): e202100693.
  • [5]. Kırpık, H, Kose, M, Elmes, RBP, Karabork, M. 2024. BODIPY- imine based fluorescence “turn on” chemosensor for selective sensing of Hg2+. Journal of Photochemistry and Photobiology A: Chemistry; 451: 115541.
  • [6]. Huang, PJ, Kumarasamy, K, Devendhiran, T, Chen, YC, Dong, TY, Lin, MC. 2021. BODIPY-based hydroxypyridyl derivative as a highly Ni2+-selective fluorescent chemosensor. Journal of Molecular Structure; 1246: 131281.
  • [7]. Ksenofontova, KV, Kerner, AA, Ksenofontov, AA, Shagurin, AY, Bocharov, PS, Lukanov, MM, Kayumov, AR, Zhuravleva, DE, Iskhakova, ZI, Molchanov, EE, Merkushev, DA, Khodov, IA, Marfin, YS. 2022. Amine-Reactive BODIPY Dye: Spectral Properties and Application for Protein Labeling. Molecules; 27 (22): 7911.
  • [8]. Guseva, GB, Antina, EV, Berezin, MB, Pavelyev, RS, Kayumov, AR, Sharafutdinov, IS, Lisovskaya, SA, Lodochnikova, OA, Islamov, DR, Usachev, KS, Boichuk, SV, Nikitina, LE. 2020. Meso-substituted-BODIPY based fluorescent biomarker: Spectral characteristics, photostability and possibilities for practical application. Journal of Photochemistry and Photobiology A: Chemistry; 401: 112783.
  • [9]. Madrid-Úsuga, D, Reina, JH. 2021. Molecular Structure, Quantum Coherence, and Solvent Effects on the Ultrafast Electron Transport in BODIPY–C60 Derivatives. The Journal of Physical Chemistry A; 125 (12): 2518–2531.
  • [10]. Shao, X, Fan, X, Cao, X, Li, W, Meng, B, Liu, J, Wang, L. 2023. Electron-Transporting Properties and Ultrasmall Band Gap of BODIPY-Based Conjugated Polymers: Teach an Old Dog New Tricks. Macromolecules; 56 (23): 9489–9497.
  • [11]. Gül, EY, Karataş, EA, Doğan, HA, Karataş, ÖF, Çoşut, B, Eçik, ET. 2023. Erlotinib-Modified BODIPY Photosensitizers for Targeted Photodynamic Therapy. ChemMedChem; 18 (2): e202200439.
  • [12]. Gül, EY, Erdem, M, Kazan, HH, Eçik, ET. 2023. Thiophene BODIPY-substituted cyclotriphosphazene-derived photosensitizers for photodynamic therapy applications. New Journal of Chemistry; 47 (37): 17469–17480.
  • [13]. Ma, RZ, Yao, QC, Yang, X, Xia, M. 2012. Synthesis, characterization and photoluminescence properties of strong fluorescent BF2 complexes bearing (2-quinolin-2-yl)phenol ligands. Journal of Fluorine Chemistry; 137: 93–98.
  • [14]. Bartelmess, J, Weare, WW. 2013. Preparation and characterization of multi-cationic BODIPYs and their synthetically versatile precursors. Dyes and Pigments; 97 (1): 1–8.
  • [15]. Sarıkaya, SY, Yeşilot, S, Kılıç, A, Okutan, E. 2018. Novel BODIPY-Cyclotriphosphazene- Fullerene triads: Synthesis, characterization and singlet oxygen generation efficiency. Dyes and Pigments; 153: 26–34.
  • [16]. Bozdemir, OA, Cakmak, Y, Sozmen, F, Ozdemir, T, Siemiarczuk, A, Akkaya, EU. 2010. Synthesis of Symmetrical Multichromophoric Bodipy Dyes and Their Facile Transformation into Energy Transfer Cassettes. Chemistry – A European Journal; 16 (21): 6346–6351.
  • [17]. Poddar, M, Misra, R. 2020. Recent advances of BODIPY based derivatives for optoelectronic applications. Coordination Chemistry Reviews; 421: 213462.
  • [18]. Ilina, K, Henary, M. 2021. Cyanine Dyes Containing Quinoline Moieties: History, Synthesis, Optical Properties, and Applications. Chemistry – A European Journal; 27 (13): 4230–4248.
  • [19]. Alnoman, RB, Parveen, S, Khan, A, Knight, JG, Hagar, M. 2022. New quinoline-based BODIPYs as EGFR/VEGFR-2 inhibitors: Molecular docking, DFT and in vitro cytotoxicity on HeLa cells. Journal of Molecular Structure; 1247: 131312.
  • [20]. Gümüş, A, Gümüş, S. 2022. Synthesis of Quinoline-Pyrene Derivatives and Theoretical Investigation of Their Fluorescence and Electronic Properties. ChemistrySelect; 7 (47): e202203958.
  • [21]. Glanzmann, N, Lemos, ASO, Meinel, RS, Branca, MT, Mayrink, NS, Nunes, IKC, Pereira, HMG, Coimbra, ES, Fabri, RL, Silva, AD. 2024. New Quinoline Derivatives and their Antimicrobial Potential Against Candida Albicans and Staphylococcus Aureus. ChemistrySelect; 9 (36): e202401828.
  • [22]. Arslan, BS, Derin, Y, Mısır, BA, Kaya, S, Şişman, İ, Tutar, A, Nebioğlu, M. 2022. Effect of electron donors on the photophysical and theoretical properties of BODIPY dyes based on tetrazolo[1,5-a]quinoline. Journal of Molecular Structure; 1267: 133608.
  • [23]. Derin, Y, Arslan, BS, Mısır, BA, Şişman, İ, Nebioğlu, M, Tutar, A. 2020. Synthesis and photophysical investigation of AIEgen dyes bearing quinoline and BODIPY scaffolds. Chemistry of Heterocyclic Compounds; 56 (12): 1542–1547.
  • [24]. Kumarasamy, K, Devendhiran, T, Chien, WJ, Lin, MC, Ramasamy, SK, Yang, JJ. 2024. Bodipy-based quinoline derivative as a highly Hg2+-selective fluorescent chemosensor and its potential applications. Methods; 223: 35–44.
  • [25]. Gao, T, He, H, Huang, R, Zheng, M, Wang, FF, Hu, YJ, Jiang, FL, Liu, Y. 2017. BODIPY-based fluorescent probes for mitochondria-targeted cell imaging with superior brightness, low cytotoxicity and high photostability. Dyes and Pigments; 141: 530–535.
  • [26]. Özcan, E, Keşan, G, Topaloğlu, B, Eçik, ET, Dere, A, Yakuphanoglu, F, Çoşut, B. 2018. Synthesis, photophysical, DFT and photodiode properties of subphthalocyanine–BODIPY dyads. New Journal of Chemistry; 42 (7): 4972–4980.
  • [27]. Sarıkaya, SY, Yeşilot, S, Kılıç, A, Okutan, E. 2019. NIR BODIPY-Cyclotriphosphazene-Fullerene assemblies: Photophyisical properties and photosensitized generation of singlet oxygen. Dyes and Pigments; 162: 734–740.
  • [28]. Gümüş, A, Okumuş, V, Gümüş, S. 2018. Synthesis of 2-substituted 8-propargyloxyquinoline derivatives and determination of their antioxidant, antibacterial, and DNA binding activities. Turkish Journal of Chemistry; 42 (5): 1358–1369.

Multistep Synthesis and Structural Analysis of a BODIPY-Quinoline Compound

Year 2025, Volume: 21 Issue: 3, 35 - 42, 26.09.2025
https://doi.org/10.18466/cbayarfbe.1582319

Abstract

This article describes the design, synthesis, purification and characterization of a new BODIPY-quinoline compound (6). The molecular design strategy is based on the placement of azido substituents at the 3 and 5 positions of the BODIPY skeleton, preparation of propargyl-quinoline compound (5) and the click reaction between distyryl-BODIPY (4) and propargyl-quinoline (5). The structures of all the new compounds were confirmed by MALDI-MS, 1H and 13C NMR spectroscopic techniques. This combination allows the formation of binding sites for metal ions. Thus, the BODIPY-quinoline compound presented in this study is promising for the development of novel fluorescent sensors. The presented synthetic strategy can also be used to synthesize other BODIPY derivatives needed for various applications.

Ethical Statement

There are no ethical issues after the publication of this manuscript.

Supporting Institution

Karabuk University

Project Number

KBÜBAP-24-DS-103

Thanks

I am grateful for the financial support from Scientific Reseach Unit of Karabuk University (Grant No. KBÜBAP-24-DS-103)

References

  • [1]. Dai, Y, Sun, J, Zhang, X, Zhao, J, Yang, W, Zhou, J, Gao, Z, Wang, Q, Yu, F, Wang, B. 2024. Supramolecular assembly boosting the phototherapy performances of BODIPYs. Coordination Chemistry Reviews; 517: 216054.
  • [2]. Yilmaz, RF, Derin, Y, Misir, BA, Atalay, VE, Tutar, ÖF, Ökten, S, Tutar, A. 2023. Synthesis and spectral properties of symmetrically arylated BODIPY dyes: Experimental and computational approach. Journal of Molecular Structure; 1291: 135962.
  • [3]. Joshi, DK, Betancourt, F, Pilkington, M, Yan, H. 2023. Neutral BODIPY derivatives as photosensitizers. Journal of Photochemistry and Photobiology A: Chemistry; 442: 114770.
  • [4]. Gündüz, EÖ, Gedik, ME, Günaydın, G, Okutan, E. 2022. Amphiphilic Fullerene-BODIPY Photosensitizers for Targeted Photodynamic Therapy. ChemMedChem; 17 (6): e202100693.
  • [5]. Kırpık, H, Kose, M, Elmes, RBP, Karabork, M. 2024. BODIPY- imine based fluorescence “turn on” chemosensor for selective sensing of Hg2+. Journal of Photochemistry and Photobiology A: Chemistry; 451: 115541.
  • [6]. Huang, PJ, Kumarasamy, K, Devendhiran, T, Chen, YC, Dong, TY, Lin, MC. 2021. BODIPY-based hydroxypyridyl derivative as a highly Ni2+-selective fluorescent chemosensor. Journal of Molecular Structure; 1246: 131281.
  • [7]. Ksenofontova, KV, Kerner, AA, Ksenofontov, AA, Shagurin, AY, Bocharov, PS, Lukanov, MM, Kayumov, AR, Zhuravleva, DE, Iskhakova, ZI, Molchanov, EE, Merkushev, DA, Khodov, IA, Marfin, YS. 2022. Amine-Reactive BODIPY Dye: Spectral Properties and Application for Protein Labeling. Molecules; 27 (22): 7911.
  • [8]. Guseva, GB, Antina, EV, Berezin, MB, Pavelyev, RS, Kayumov, AR, Sharafutdinov, IS, Lisovskaya, SA, Lodochnikova, OA, Islamov, DR, Usachev, KS, Boichuk, SV, Nikitina, LE. 2020. Meso-substituted-BODIPY based fluorescent biomarker: Spectral characteristics, photostability and possibilities for practical application. Journal of Photochemistry and Photobiology A: Chemistry; 401: 112783.
  • [9]. Madrid-Úsuga, D, Reina, JH. 2021. Molecular Structure, Quantum Coherence, and Solvent Effects on the Ultrafast Electron Transport in BODIPY–C60 Derivatives. The Journal of Physical Chemistry A; 125 (12): 2518–2531.
  • [10]. Shao, X, Fan, X, Cao, X, Li, W, Meng, B, Liu, J, Wang, L. 2023. Electron-Transporting Properties and Ultrasmall Band Gap of BODIPY-Based Conjugated Polymers: Teach an Old Dog New Tricks. Macromolecules; 56 (23): 9489–9497.
  • [11]. Gül, EY, Karataş, EA, Doğan, HA, Karataş, ÖF, Çoşut, B, Eçik, ET. 2023. Erlotinib-Modified BODIPY Photosensitizers for Targeted Photodynamic Therapy. ChemMedChem; 18 (2): e202200439.
  • [12]. Gül, EY, Erdem, M, Kazan, HH, Eçik, ET. 2023. Thiophene BODIPY-substituted cyclotriphosphazene-derived photosensitizers for photodynamic therapy applications. New Journal of Chemistry; 47 (37): 17469–17480.
  • [13]. Ma, RZ, Yao, QC, Yang, X, Xia, M. 2012. Synthesis, characterization and photoluminescence properties of strong fluorescent BF2 complexes bearing (2-quinolin-2-yl)phenol ligands. Journal of Fluorine Chemistry; 137: 93–98.
  • [14]. Bartelmess, J, Weare, WW. 2013. Preparation and characterization of multi-cationic BODIPYs and their synthetically versatile precursors. Dyes and Pigments; 97 (1): 1–8.
  • [15]. Sarıkaya, SY, Yeşilot, S, Kılıç, A, Okutan, E. 2018. Novel BODIPY-Cyclotriphosphazene- Fullerene triads: Synthesis, characterization and singlet oxygen generation efficiency. Dyes and Pigments; 153: 26–34.
  • [16]. Bozdemir, OA, Cakmak, Y, Sozmen, F, Ozdemir, T, Siemiarczuk, A, Akkaya, EU. 2010. Synthesis of Symmetrical Multichromophoric Bodipy Dyes and Their Facile Transformation into Energy Transfer Cassettes. Chemistry – A European Journal; 16 (21): 6346–6351.
  • [17]. Poddar, M, Misra, R. 2020. Recent advances of BODIPY based derivatives for optoelectronic applications. Coordination Chemistry Reviews; 421: 213462.
  • [18]. Ilina, K, Henary, M. 2021. Cyanine Dyes Containing Quinoline Moieties: History, Synthesis, Optical Properties, and Applications. Chemistry – A European Journal; 27 (13): 4230–4248.
  • [19]. Alnoman, RB, Parveen, S, Khan, A, Knight, JG, Hagar, M. 2022. New quinoline-based BODIPYs as EGFR/VEGFR-2 inhibitors: Molecular docking, DFT and in vitro cytotoxicity on HeLa cells. Journal of Molecular Structure; 1247: 131312.
  • [20]. Gümüş, A, Gümüş, S. 2022. Synthesis of Quinoline-Pyrene Derivatives and Theoretical Investigation of Their Fluorescence and Electronic Properties. ChemistrySelect; 7 (47): e202203958.
  • [21]. Glanzmann, N, Lemos, ASO, Meinel, RS, Branca, MT, Mayrink, NS, Nunes, IKC, Pereira, HMG, Coimbra, ES, Fabri, RL, Silva, AD. 2024. New Quinoline Derivatives and their Antimicrobial Potential Against Candida Albicans and Staphylococcus Aureus. ChemistrySelect; 9 (36): e202401828.
  • [22]. Arslan, BS, Derin, Y, Mısır, BA, Kaya, S, Şişman, İ, Tutar, A, Nebioğlu, M. 2022. Effect of electron donors on the photophysical and theoretical properties of BODIPY dyes based on tetrazolo[1,5-a]quinoline. Journal of Molecular Structure; 1267: 133608.
  • [23]. Derin, Y, Arslan, BS, Mısır, BA, Şişman, İ, Nebioğlu, M, Tutar, A. 2020. Synthesis and photophysical investigation of AIEgen dyes bearing quinoline and BODIPY scaffolds. Chemistry of Heterocyclic Compounds; 56 (12): 1542–1547.
  • [24]. Kumarasamy, K, Devendhiran, T, Chien, WJ, Lin, MC, Ramasamy, SK, Yang, JJ. 2024. Bodipy-based quinoline derivative as a highly Hg2+-selective fluorescent chemosensor and its potential applications. Methods; 223: 35–44.
  • [25]. Gao, T, He, H, Huang, R, Zheng, M, Wang, FF, Hu, YJ, Jiang, FL, Liu, Y. 2017. BODIPY-based fluorescent probes for mitochondria-targeted cell imaging with superior brightness, low cytotoxicity and high photostability. Dyes and Pigments; 141: 530–535.
  • [26]. Özcan, E, Keşan, G, Topaloğlu, B, Eçik, ET, Dere, A, Yakuphanoglu, F, Çoşut, B. 2018. Synthesis, photophysical, DFT and photodiode properties of subphthalocyanine–BODIPY dyads. New Journal of Chemistry; 42 (7): 4972–4980.
  • [27]. Sarıkaya, SY, Yeşilot, S, Kılıç, A, Okutan, E. 2019. NIR BODIPY-Cyclotriphosphazene-Fullerene assemblies: Photophyisical properties and photosensitized generation of singlet oxygen. Dyes and Pigments; 162: 734–740.
  • [28]. Gümüş, A, Okumuş, V, Gümüş, S. 2018. Synthesis of 2-substituted 8-propargyloxyquinoline derivatives and determination of their antioxidant, antibacterial, and DNA binding activities. Turkish Journal of Chemistry; 42 (5): 1358–1369.
There are 28 citations in total.

Details

Primary Language English
Subjects Macromolecular and Materials Chemistry (Other)
Journal Section Articles
Authors

Semiha Yıldırım Sarıkaya 0000-0002-5993-3660

Project Number KBÜBAP-24-DS-103
Publication Date September 26, 2025
Submission Date November 10, 2024
Acceptance Date April 10, 2025
Published in Issue Year 2025 Volume: 21 Issue: 3

Cite

APA Yıldırım Sarıkaya, S. (2025). Multistep Synthesis and Structural Analysis of a BODIPY-Quinoline Compound. Celal Bayar University Journal of Science, 21(3), 35-42. https://doi.org/10.18466/cbayarfbe.1582319
AMA Yıldırım Sarıkaya S. Multistep Synthesis and Structural Analysis of a BODIPY-Quinoline Compound. CBUJOS. September 2025;21(3):35-42. doi:10.18466/cbayarfbe.1582319
Chicago Yıldırım Sarıkaya, Semiha. “Multistep Synthesis and Structural Analysis of a BODIPY-Quinoline Compound”. Celal Bayar University Journal of Science 21, no. 3 (September 2025): 35-42. https://doi.org/10.18466/cbayarfbe.1582319.
EndNote Yıldırım Sarıkaya S (September 1, 2025) Multistep Synthesis and Structural Analysis of a BODIPY-Quinoline Compound. Celal Bayar University Journal of Science 21 3 35–42.
IEEE S. Yıldırım Sarıkaya, “Multistep Synthesis and Structural Analysis of a BODIPY-Quinoline Compound”, CBUJOS, vol. 21, no. 3, pp. 35–42, 2025, doi: 10.18466/cbayarfbe.1582319.
ISNAD Yıldırım Sarıkaya, Semiha. “Multistep Synthesis and Structural Analysis of a BODIPY-Quinoline Compound”. Celal Bayar University Journal of Science 21/3 (September2025), 35-42. https://doi.org/10.18466/cbayarfbe.1582319.
JAMA Yıldırım Sarıkaya S. Multistep Synthesis and Structural Analysis of a BODIPY-Quinoline Compound. CBUJOS. 2025;21:35–42.
MLA Yıldırım Sarıkaya, Semiha. “Multistep Synthesis and Structural Analysis of a BODIPY-Quinoline Compound”. Celal Bayar University Journal of Science, vol. 21, no. 3, 2025, pp. 35-42, doi:10.18466/cbayarfbe.1582319.
Vancouver Yıldırım Sarıkaya S. Multistep Synthesis and Structural Analysis of a BODIPY-Quinoline Compound. CBUJOS. 2025;21(3):35-42.