Journal of Fluorescence

, Volume 28, Issue 1, pp 277–284 | Cite as

Spectral Properties and Possibilities of meso-Substituted BODIPY Usage in Sol–Gel Process and Materials

  • A. V. Bobrov
  • S. D. Usoltsev
  • Yu S. Marfin
  • E. V. Rumyantsev
ORIGINAL ARTICLE
First Online:
Received:
Accepted:

Abstract

Hybrid materials based on organically modified silica with immobilized boron-dipyrrins (BODIPY) dyes were obtained. Spectral characteristics of the dyes were measured during the matrix formation and in obtained materials. It was stated, that immobilization does not affect the character of the absorption and fluorescence spectra of the dye, but due to the effect of fluorescent molecular rotor observed for meso-substituted BODIPY, the fluorescent quantum yields were found to increase during the matrix sealing. Quantum yield increase is linear for all of the investigated matrices except phenyl-substituted one, where the π-π interactions of the dye molecule with matrix could be observed. This effect could be used for fine control of the matrix formation process and leads to increase of the dye emission in the final material for further practical applications. All obtained hybrid materials were found to be stable upon UV light irradiation, hence immobilization enhance the stability of the dye in comparison with the BODIPY in organic solvents.

Keywords

Sol–gel Hybrid materials BODIPY Viscosity Molecular rotors 
This is a preview of subscription content, log in to check access.

Notes

Acknowledgements

The work was partially supported by the Grant of the President of the Russian Federation (МК-8835.2016.3) and the RFBR (Grant No 16-03-01028).

Supplementary material

10895_2017_2190_MOESM1_ESM.docx (6.1 mb)
Supplementary material 1 (DOCX 6237 KB)

References

  1. 1.
    Wang LY, Fang GP, Cao DR (2015) A novel phenol-based BODIPY chemosensor for selective detection Fe3+ with colorimetric and fluorometric dual-mode. Sensors Actuators B Chem 207:849–857.  https://doi.org/10.1016/j.snb.2014.10.110 CrossRefGoogle Scholar
  2. 2.
    He Y, Feng RK, Yi YR, Liu ZX (2014) Recent progress in the research of borondipyrromethene-based fluorescent ion chemosensor. Chinese J Org Chem 34:2236–2248.  https://doi.org/10.6023/cjoc201403066 CrossRefGoogle Scholar
  3. 3.
    Madhu S, Kalaiyarasi R, Basu SK, Jadhavb S, Ravikanth M (2014) A boron-dipyrrin–mercury (II) complex as a fluorescence turn-on sensor for chloride and applications towards logic gates. J Mater Chem C 2:2534–2544.  https://doi.org/10.1039/C3TC32188F CrossRefGoogle Scholar
  4. 4.
    Liu J, He XX, Zhang J, He T, Huang LQ, Shen JQ, Li D, Qiu HY, Yin SC (2015) A BODIPY derivative for colorimetric and fluorometric sensing of fluoride ion and its logic gates behavior. Sensors Actuators B Chem 208:538–545.  https://doi.org/10.1016/j.snb.2014.11.094 CrossRefGoogle Scholar
  5. 5.
    Niu Li-Ya et al (2012) BODIPY-based ratiometric fluorescent sensor for highly selective detection of glutathione over cysteine and homocysteine. J Am Chem Soc 134(46): 18928–18931.  https://doi.org/10.1021/ja309079f CrossRefPubMedGoogle Scholar
  6. 6.
    Gareis T, Huber C, Wolfbeis OS, Daub J (1997) Phenol/phenolatedependent on/off switching of the luminescence of 4,4-difluoro-4- Bora-3a,4a-diaza-S-indacenes. Chem Commun 18:1717–1718.  https://doi.org/10.1039/A703536E CrossRefGoogle Scholar
  7. 7.
    Werner T, Huber C, Heinl S, Kollmannsberger M, Daub J, Wolfbeis OS (1997) Novel optical Ph-sensor based on a boradiaza-indacene derivative. Fresenius J Anal Chem 359:150–154.  https://doi.org/10.1007/s002160050552 CrossRefGoogle Scholar
  8. 8.
    Wu Y, Štefl M, Olzyńska (2013) Molecular rheometry: direct determination of viscosity in L o and L d lipid phases via fluorescence lifetime imaging. Phys Chem Chem Phys 15(36):14986–14993.  https://doi.org/10.1039/c3cp51953h CrossRefPubMedGoogle Scholar
  9. 9.
    Sui B, Tang S, Liu T (2014) Novel BODIPY-based fluorescence turn-on sensor for Fe3+ and its bioimaging application in living cells. ACS Appl Mater Interfaces 21:18408–18412.  https://doi.org/10.1021/am506262u CrossRefGoogle Scholar
  10. 10.
    Andrea B, Costero M, Salvador AG (2014) Chromo-fluorogenic BODIPY-complexes for selective detection of V-type nerve agent surrogates. Chem Commun 50:13289–13291.  https://doi.org/10.1039/C4CC05945J CrossRefGoogle Scholar
  11. 11.
    Fengling S, Yingying X, Xu W, Jingyun W, Xiaoqing X, Xiaojun P (2014) Ratiometric fluorescent probe based on novel red-emission BODIPY for determination of bovine serum albumin. Chem Res Chin Univ 30:738–742.  https://doi.org/10.1007/s40242-014-4029-7 CrossRefGoogle Scholar
  12. 12.
    Ma D, Kim D, Seo E, Lee S, Ahn KH (2015) Ratiometric fluorescence detection of cysteine and homocysteine with a BODIPY dye by mimicking the native chemical ligation. Analyst 140:422–427.  https://doi.org/10.1039/c4an01791a CrossRefPubMedGoogle Scholar
  13. 13.
    Bahaidarah E, Harriman A, Stachelek P, Rihn S, Heyerb E, Ziessel R (2014) Fluorescent molecular rotors based on the BODIPY motif: effect of remote substituents. Photochem Photobiol Sci 10:1397–1401.  https://doi.org/10.1039/c4pp00204k CrossRefGoogle Scholar
  14. 14.
    Marfin YS, Merkushev DA, Levshanov GA, Rumyantsev EV (2014) Fluorescent properties of 8-phenylBODIPY in ethanol – ethylene glycol mixed solutions. J Fluoresc 24:1613–1619.  https://doi.org/10.1007/s10895-014-1447-3 CrossRefPubMedGoogle Scholar
  15. 15.
    Rongrong H, Lager E, Aguilar-Aguilar A, Liu J, Lam JWY, Sung HHY, Williams ID (2009) Twisted intramolecular charge transfer and aggregation-induced emission of BODIPY derivatives. J Phys Chem C 113:15845–15853.  https://doi.org/10.1021/jp902962h CrossRefGoogle Scholar
  16. 16.
    Dal Molin M, Verolet Q, Soleimanpour S, Matile S (2015) Mechanosensitive membrane probes. Chemistry 21:6012–6021.  https://doi.org/10.1002/chem.201406320 CrossRefPubMedGoogle Scholar
  17. 17.
    Haidekker M, Theodorakis E (2010) Environment-sensitive behavior of fluorescent molecular rotors. J Biol Eng 4:11–25.  https://doi.org/10.1186/1754-1611-4-11 CrossRefPubMedPubMedCentralGoogle Scholar
  18. 18.
    Benniston AC (2014) Monitoring rheological properties in biological systems by fluorescence spectroscopy using borondipyrromethene (Bodipy) dyes: a mini review. J Anal Bioanal Tech 5:1–11.  https://doi.org/10.4172/2155-9872.1000221 CrossRefGoogle Scholar
  19. 19.
    Château D, Bellier Q, Chaput F, Feneyrou P, Berginc G, Maury O, … & Parola S (2014) Efficient hybrid materials for optical power limiting at telecommunication wavelengths. J Mater Chem C 2(26):5105–5110.  https://doi.org/10.1039/C4TC00193A CrossRefGoogle Scholar
  20. 20.
    Hong X, Wang Z, Yang J, Zheng Q, Zong S, Sheng Y, … & Cui Y (2012) Silylated BODIPY dyes and their use in dye-encapsulated silica nanoparticles with switchable emitting wavelengths for cellular imaging. Analyst 137(18):4140–4149.  https://doi.org/10.1039/C2AN35389J CrossRefPubMedGoogle Scholar
  21. 21.
    Hungerford G, Allison A, McLoskey D, Kuimova MK, Yahioglu G, Suhling K (2009) Monitoring sol-to-gel transitions via fluorescence lifetime determination using viscosity sensitive fluorescent probes. J Phys Chem B 113(35):12067–12074.  https://doi.org/10.1021/jp902727y CrossRefPubMedGoogle Scholar
  22. 22.
    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(5):1517–1526.  https://doi.org/10.1007/s10895-015-1643-9 CrossRefPubMedGoogle Scholar
  23. 23.
    Marfin Yu. S., Shipalova MV, Kurzin VO, Ksenofontova KV, Solomonov AV, Rumyantsev EV (2016) Fluorescent properties of BODIPY sensors based on photoinduced electron transfer. J fluoresc.  https://doi.org/10.1007/s10895-016-1905-1 Google Scholar
  24. 24.
    Marfin SY et al (2013) Spectral and photophysical properties, photo and heat resistance of dipyrrolylmethene borofluoride complex and its hybrid material with polymethylmethacrylate. Russ J Gen Chem 83(2): 381–385.  https://doi.org/10.1134/S1070363213020242 CrossRefGoogle Scholar
  25. 25.
    Marfin YS, Vodyanova OS, Merkushev DA, Usoltsev SD, Kurzin VO, Rumyantsev EV (2016) Effect of π-extended substituents on photophysical properties of BODIPY dyes in solutions. J Fluoresc 1–11.  https://doi.org/10.1007/s10895-016-1891-3

Copyright information

© Springer Science+Business Media, LLC 2017

Authors and Affiliations

  • A. V. Bobrov
    • 1
  • S. D. Usoltsev
    • 1
  • Yu S. Marfin
    • 1
  • E. V. Rumyantsev
    • 1
  1. 1.Department of Inorganic ChemistryIvanovo State University of Chemistry and TechnologyIvanovoRussia

Personalised recommendations