Abstract
The UV/Vis absorption and fluorescence properties of dibenzofluorescein (DBFL) in organic solvents were measured and used to shed light on the possible presence of its tautomers or various prototropic forms. DBFL in aprotic solvents mainly exists in two tautomeric forms, viz. quinoid and lactone, but neither are efficiently fluorescent. In protic solvents, such as methanol and ethanol, both the monoanion and neutral quinoid are present and showed the highest fluorescence quantum yield. In contrast, DBFL is fully dissociated to the monoanion and dianion in deionized water.
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References
M. A. Kuhn and R. P. Haugland, US Pat. 5516864, 1993.
L. G. Lee, C. R. Connell, S. L. Woo, R. D. Cheng, B. F. McArdle, C. W. Fuller, N. D. Halloran and R. K. Wilson, ‘DNA sequencing with dye-labeled terminators and T7 DNA polymerase: effect of dyes and dNTPs on incorporation of dye-terminators and probability analysis of termination fragments’, Nucleic Acids Res., 1992, 20, 2471–2483.
T. Kempe, US Pat. 6534646, 2003.
L. G. Lee, US Pat. 4933471, 1990.
Z. Diwu and R. P. Haugland, US Pat. 5773236, 1998.
J. Liu, Z. Diwu and W.-Y. Leung, ‘Synthesis and photophysical properties of new fluorinated benzo[c]xanthene dyes as intracellular pH indicators’, Bioorg. Med. Chem. Lett., 2001, 11, 2903–2905.
A. Gómez-Hens and M. P. Aguilar-Caballos, ‘Long-wavelength fluorophores–new trends in their analytical use’, TrAC, Trends Anal. Chem., 2006, 23, 127–136.
K. J. Thomas, D. B. Sherman, T. J. Amiss, S. A. Andaluz and J. B. Pitner, ‘A long-wavelength fluorescent glucose biosensor based on bioconjugates of galactose/glucose binding protein and Nile Red derivatives’, Diabetes Technol. Ther., 2006, 8, 261–268.
X.-F. Zhang et al., Talanta, 2007, submitted.
L. G. Lee, G. M. Berry and C.-H. Chen, ‘Vita blue: A new 633-nm excitable fluorescent dye for cell analysis’, Cytometry, 1989, 10, 151–164.
H. Zhang, Y. Zhou, M. Zhang, T. Shen, Y. Li and D. Zhu, ‘Photoinduced interaction between fluorescein ester derivatives and CdS colloid’, J. Colloid Interface Sci., 2003, 264(1), 290–295.
H. Zhang, Y. Zhou, M. Zhang, T. Shen, Y. Li and D. Zhu, ‘Photoinduced charge separation across colloidal TiO2 and fluorescein derivatives’, J. Phys. Chem. B, 2002, 106(37), 9597–9603.
H. Diehl, ‘Absorbance of the various prototropic forms of yellow fluorescein in aqueous solution’, Talanta, 1989, 36, 413–415.
H. Diehl and N. Horchak-Morris, ‘The absorbance of fluorescein in the ultraviolet, as a function of pH’, Talanta, 1987, 34, 739–741.
A. Song, J. Zhang, M. Zhang, T. Shen and J. A. Tang, ‘Spectral properties and structure of fluorescein and its alkyl derivatives in micelles’, Colloids Surf., A, 2000, 167, 253–262.
Y. H. Jang, S. Hwang and D. S. Chung, ‘Tautomeric equilibrium of fluorescein in solution: ab initio calculations’, Chem. Lett., 2001, 1316–1317.
K. Tanaka, T. Miura, N. Umezawa, Y. Urano, K. Kikuchi, T. Higuchi and T. Nagano, ‘Rational design of fluorescein-based fluorescence probes. Mechanism-based design of a maximum fluorescence probe for singlet oxygen’, J. Am. Chem. Soc., 2001, 123, 2530–2536.
J. A. Dean, Lange’s Handbook of Chemistry (15th edn), McGraw-Hill, New York, 1999, p. 7.28.
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Zhang, X., Liu, Q., Son, A. et al. Photophysical properties of dibenzofluorescein and the presence of its tautomers or prototropic forms in organic solvents. Photochem Photobiol Sci 7, 299–302 (2008). https://doi.org/10.1039/b717849b
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DOI: https://doi.org/10.1039/b717849b