Advertisement

Influence of 1,3,5-triazine Core and Electron Donor Group in Photophysical Properties of BODIPY Dyes

  • María Teresa Páez González
  • Shaiani Maria Gil de Mello
  • Silva Emery Flavio da Email author
ORIGINAL ARTICLE
  • 50 Downloads

Abstract

The relationship between the number of BODIPY in a compound and the increase on its fluorescence has been established such as an aggregation induced by multiple BODIPY. We aimed to determine the influence of an electron donor substituent in the BODIPY-triazine system. In this sense, as a first step, we collected data such as photophysical characteristics about BODIPY without substituent and meso-triazine-BODIPY system. Then, three more meso-triazine-BODIPY were synthetized by Lyndsey method. In addition, absorption and emission spectra, fluorescence quantum yields and time-resolved fluorescence data were obtained. Furthermore, solvatochromism was determined by solvent descriptors and photophysical parameters. Finally, the results showed that the triazine core stabilized the system and we observed that the number of BODIPY increased fluorescence mainly in polar solvents. While electron donation maintained the conjugation that reduced the influence of the solvent on the photophysical characteristics.

Keywords

1,3,5-triazine BODIPY Solvatochromism Fluorescence 

Notes

Acknowledgements

The authors gratefully acknowledge the financial support of Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq, Grants numbers 165417/2014-5 and 168073/2017-0) and CAPES (This work was carried out with the support of the Coordination of Improvement of Higher Education Personnel - Brazil (CAPES)- Financing code 001). We also would like to acknowledge the Analytical Centre of NPPNS (FCFRP-USP, Brazil) for the Mass Spectrometry analysis.

References

  1. 1.
    Hawe A, Sutter M, Jiskoot W (2008) Extrinsic fluorescent dyes as tools for protein characterization. Pharm Res 25:1487–1499CrossRefGoogle Scholar
  2. 2.
    Clegg RM (1992) [18] Fluorescence resonance energy transfer and nucleic acids. In: Methods in enzymology. Elsevier, pp 353–388Google Scholar
  3. 3.
    Terasaki M, Loew L, Lippincott-Schwartz J, Zaal K (1998) Fluorescent staining of subcellular organelles: ER, Golgi complex, and mitochondria. Curr Protoc cell Biol 4Google Scholar
  4. 4.
    Ueno T, Nagano T (2011) Fluorescent probes for sensing and imaging. Nat Methods 8:642–645CrossRefGoogle Scholar
  5. 5.
    Sun H, Scharff-Poulsen AM, Gu H, Almdal K (2006) Synthesis and characterization of ratiometric, pH sensing nanoparticles with covalently attached fluorescent dyes. Chem Mater 18:3381–3384CrossRefGoogle Scholar
  6. 6.
    Wolfbeis OS (2005) Materials for fluorescence-based optical chemical sensors. J Mater Chem 15:2657–2669CrossRefGoogle Scholar
  7. 7.
    Bañuelos J, Arbeloa FL, Arbeloa T, et al (2012) BODIPY laser dyes applied in sensing and monitoring environmental properties. Appl Sci Innov Pvt LtdGoogle Scholar
  8. 8.
    Yang Y, Zhang L, Gao C, Xu L, Bai S, Liu X (2014) Pyrene-based BODIPY: synthesis, photophysics and lasing properties under UV-pumping radiation. RSC Adv 4:38119–38123CrossRefGoogle Scholar
  9. 9.
    Padalkar VS, Patil VS, Sekar N (2011) Synthesis and photo-physical properties of fluorescent 1, 3, 5-triazine styryl derivatives. Chem Cent J 5:77CrossRefGoogle Scholar
  10. 10.
    Feng H, Geng X, Lin J, Guo H, Yang F (2018) Novel fluorescent liquid crystals: synthesis, mesomorphism and fluorescence of triphenylene-Bodipy derivatives based on 1,3,5-triazine core. Liq Cryst 45:1470–1476.  https://doi.org/10.1080/02678292.2018.1446554 CrossRefGoogle Scholar
  11. 11.
    Zhou W, Guo H, Lin J, Yang F (2018) Multiple BODIPY derivatives with 1, 3, 5-triazine as core: balance between fluorescence and numbers of BODIPY units. J Iran Chem Soc 15:2559–2566CrossRefGoogle Scholar
  12. 12.
    Williams ATR, Winfield SA, Miller JN (1983) Relative fluorescence quantum yields using a computer-controlled luminescence spectrometer. Analyst 108:1067–1071CrossRefGoogle Scholar
  13. 13.
    Resch-Genger U, DeRose PC (2010) Fluorescence standards: classification, terminology, and recommendations on their selection, use, and production (IUPAC technical report). Pure Appl Chem 82:2315–2335CrossRefGoogle Scholar
  14. 14.
    Marfin YS, Merkushev DA, Usoltsev SD, Shipalova MV, Rumyantsev EV (2015) Fluorescent properties of 8-substituted BODIPY dyes: influence of solvent effects. J Fluoresc 25:1517–1526.  https://doi.org/10.1007/s10895-015-1643-9 CrossRefGoogle Scholar
  15. 15.
    Littler BJ, Miller MA, Hung C-H, Wagner RW, O'Shea DF, Boyle PD, Lindsey JS (1999) Refined synthesis of 5-substituted dipyrromethanes. J Org Chem 64:1391–1396CrossRefGoogle Scholar
  16. 16.
    de Rezende LCD, Vaidergorn MM, Moraes JCB, da Silva Emery F (2014) Synthesis, photophysical properties and solvatochromism of meso-substituted tetramethyl BODIPY dyes. J Fluoresc 24:257–266CrossRefGoogle Scholar
  17. 17.
    Atkins P, de Paula J (2006) Molecular spectroscopy: Electronic transitions In: Atkins’ Physical Chemistry pp 496–500Google Scholar
  18. 18.
    Bohle M, Borzilleri RM, Döpp D, et al (2014) Science of synthesis: Houben-Weyl methods of molecular transformations Vol. 17: Six-membered Hetarenes with two unlike or more than two heteroatoms and fully unsaturated larger-ring heterocycles. ThiemeGoogle Scholar
  19. 19.
    Swavey S, Quinn J, Coladipietro M, Cox KG, Brennaman MK (2017) Tuning the photophysical properties of BODIPY dyes through extended aromatic pyrroles. RSC Adv 7:173–179.  https://doi.org/10.1039/c6ra26331c CrossRefGoogle Scholar
  20. 20.
    Di Carlo G, Caramori S, Casarin L et al (2017) Charge transfer dynamics in β- and Meso-substituted Dithienylethylene porphyrins. J Phys Chem C 121:18385–18400.  https://doi.org/10.1021/acs.jpcc.7b05823 CrossRefGoogle Scholar
  21. 21.
    Zhao N, Xuan S, Fronczek FR, Smith KM, Vicente MGH (2017) Enhanced Hypsochromic shifts, quantum yield, and π–π interactions in a meso,β-Heteroaryl-fused BODIPY. J Org Chem 82:3880–3885.  https://doi.org/10.1021/acs.joc.6b02981 CrossRefGoogle Scholar
  22. 22.
    Liao J, Zhao H, Xu Y, Zhou W, Peng F, Wang Y, Fang Y (2017) Novel BODIPY dyes with electron donor variety for dye-sensitized solar cells. RSC Adv 7:33975–33985.  https://doi.org/10.1039/C7RA04402J CrossRefGoogle Scholar
  23. 23.
    Curwiel VB (1997) Regulation of photosynthesis and energy dissipation in triazine-resistant and susceptible Chenopodium album. CurwielGoogle Scholar
  24. 24.
    Morgan E (1990) Vogel’s textbook of practical organic chemistry. 5th edn. Endeavour 14:148.  https://doi.org/10.1016/0160-9327(90)90017-L CrossRefGoogle Scholar
  25. 25.
    Yang X, Zhang X-F, Lu X, Yu C, Jiao L (2015) Red fluorescent monobenzo-BODIPY dyes: solvent effects on spectra and efficient fluorescence quenching by quinones and phenols. J Photochem Photobiol A Chem 297:39–44.  https://doi.org/10.1016/j.jphotochem.2014.10.013 CrossRefGoogle Scholar
  26. 26.
    Reichardt C (1994) Solvatochromic dyes as solvent polarity indicators. Chem Rev 94:2319–2358.  https://doi.org/10.1021/cr00032a005 CrossRefGoogle Scholar
  27. 27.
    Catalán J (2009) Toward a generalized treatment of the solvent effect based on four empirical scales: dipolarity (SdP, a new scale), polarizability (SP), acidity (SA), and basicity (SB) of the medium. J Phys Chem B 113:5951–5960CrossRefGoogle Scholar
  28. 28.
    Boens N, Wang L, Leen V, Yuan P, Verbelen B, Dehaen W, van der Auweraer M, de Borggraeve WD, van Meervelt L, Jacobs J, Beljonne D, Tonnelé C, Lazzaroni R, Ruedas-Rama MJ, Orte A, Crovetto L, Talavera EM, Alvarez-Pez JM (2014) 8-HaloBODIPYs and their 8-(C, N, O, S) substituted analogues: solvent dependent UV–vis spectroscopy, variable temperature NMR, crystal structure determination, and quantum chemical calculations. J Phys Chem A 118:1576–1594CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Department of Pharmaceutical Sciences, School of Pharmaceutical Sciences of Ribeirão PretoUniversity of São PauloRibeirão PretoBrazil

Personalised recommendations