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.
Similar content being viewed by others
References
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
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
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
Aliaga C, Rezende MC, Tirapegui C (2009) A new probe for hydrogen abstraction and radical detection. Tetrahedron 65:6025–6028
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
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
Katritzky AR, Lloyd JM, Patel RJ (1982) The preparation of pyridiniums from pyryliums. J Chem Soc Perkin Trans 1:117–123
Katritzky AR, Thind SS (1980) The synthesis and reactions of sterically constrained pyrylium and pyridinium salts. J Chem Soc Perkin Trans 1:1895–1900
Knyazhanskii MI, Tymyanskii YR, Feigelman VM, Katritzky AR (1987) Pyridinium salts: luminescent spectroscopy and photochemistry. Heterocycles 26:2963–2982
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
Lakowicz JR (1999) Principles of fluorescence spectroscopy, 2nd edn. Kluwer, New York
Williams ATR, Winfield SA, Miller JN (1983) Relative fluorescence quantum yields using a computer controlled luminescence spectrometer. Analyst 108:1067–1072
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
Corresponding author
Rights and permissions
About this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10895-015-1579-0