Skip to main content
Log in

TEMPO-Attached Pre-fluorescent Probes Based on Pyridinium Fluorophores

  • ORIGINAL PAPER
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

The photophysical behavior of three pyridinium-derived fluorophores, the N-aryl-2,4,6-triphenylpyridinium, the N-aryl-5,6-dihydro-2,4-diphenylbenzo[h]quinolinium and the N-aryl-5,6,8,9-tetrahydro-7-phenyldibenzo[c,h]acridinium perchlorates, was investigated. Comparison of their fluorescence quantum yields led to the preparation of a novel, more sensitive pyridinium-based, TEMPO-attached prefluorescent probe for H-abstraction processes, the N-{4-[4-(N-oxyl-2,2,6,6-tetramethylpiperidinyl)carbonylamino]phenyl}-5,6,8,9-tetrahydro-7-phenyldibenzo[c,h]-acridinium perchlorate.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Scheme 2
Scheme 3
Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. Scaiano JC, Aliaga C, Chrétien MN, Frenette M, Focsaneanu KS, Mikelsons L (2005) Fluorescence sensor applications as detectors for DNA damage, free radical formation, and in microlithography. Pure Appl Chem 77:1009–1018

    Article  CAS  Google Scholar 

  2. Green SA, Simpson DJ, Zhou GP, Ho S, Blough NVJ (1990) Intramolecular quenching of excited singlet states by stable nitroxyl radicals. J Am Chem Soc 112:7337–7346

    Article  CAS  Google Scholar 

  3. Aliaga C, Fuentealba P, Rezende MC, Cárdenas C (2014) Mechanism of fluorophore quenching in a pre-fluorescent nitroxide probe: a theoretical illustration. Chem Phys Lett 593:89–92

    Article  CAS  Google Scholar 

  4. Aliaga C, Rezende MC, Tirapegui C (2009) A new probe for hydrogen abstraction and radical detection. Tetrahedron 65:6025–6028

    Article  CAS  Google Scholar 

  5. Aliaga C, Aspée A, Scaiano JC (2003) A new method to study antioxidant capability: hydrogen transfer from phenols to a prefluorescent nitroxide. Org Lett 22:4145–4148

    Article  Google Scholar 

  6. Katritzky AR, Gruntz U, Kenny DH, Rezende MC, Sheikh H (1979) Heterocycles in organic synthesis. Part 10. Conversion of amines into esters. J Chem Soc Perkin Trans 1:430–432

    Article  Google Scholar 

  7. Katritzky AR, Lloyd JM, Patel RJ (1982) The preparation of pyridiniums from pyryliums. J Chem Soc Perkin Trans 1:117–123

    Article  Google Scholar 

  8. Katritzky AR, Thind SS (1980) The synthesis and reactions of sterically constrained pyrylium and pyridinium salts. J Chem Soc Perkin Trans 1:1895–1900

    Article  Google Scholar 

  9. Knyazhanskii MI, Tymyanskii YR, Feigelman VM, Katritzky AR (1987) Pyridinium salts: luminescent spectroscopy and photochemistry. Heterocycles 26:2963–2982

    Article  CAS  Google Scholar 

  10. Kharlanov VA, Knyazhansky MI (1999) The dependence of photoinduced adiabatic transformations and fluorescence in 2, 4, 6-triarylsubstituted pyridinium cations on environment. J Photochem Photobiol A: Chem 125:21–27

    Article  CAS  Google Scholar 

  11. Lakowicz JR (1999) Principles of fluorescence spectroscopy, 2nd edn. Kluwer, New York

    Book  Google Scholar 

  12. Williams ATR, Winfield SA, Miller JN (1983) Relative fluorescence quantum yields using a computer controlled luminescence spectrometer. Analyst 108:1067–1072

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was financed by FONDECYT project 1110736 F. C. thanks Becas Chile. We thank Prof. J. C. Scaiano and M. Decan for allowing the photochemical and chemical characterization of compounds 1b, 2b and 3b.

Funding

This study was funded by 1110736 FONDECYT Project.

Conflict of Interest

The authors declare that they have no conflict of interest

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Carolina Aliaga.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Aliaga, C., Celis, F., Lühr, S. et al. TEMPO-Attached Pre-fluorescent Probes Based on Pyridinium Fluorophores. J Fluoresc 25, 979–983 (2015). https://doi.org/10.1007/s10895-015-1579-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-015-1579-0

Keywords

Navigation