Berberine cation: A fluorescent chemosensor for alkanes and other low-polarity compounds. An explanation of this phenomenon

Organic Letters

Volumn 2, Issue 15, 2000, Pages 2311-2313

  Cossío, Fernando P ^a   Arrieta, Ana ^a   Cebolla, Vicente L ^b   Membrado, Luis ^b   Vela, Jesús ^c   Garriga, Rosa ^b   Domingo, María P ^b  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b INSTITUTO DE CARBOQUÍMICA   (Spain)

^c UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001701605     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006075p     Document Type: Article

References (10)

1. de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
2. Baeyens, W.R.G. In Fluorescence and Phosphorescence of Pharmaceuticals, in Molecular Luminiscence Spectroscopy. Methods and Applications: Part 1; Schulman, S. G., Ed.; Vol 77 in Chemical Analysis (Elving, P. J., Winefordner, J. D., Eds.), Wiley Interscience: New York, 1985; Chapter 2.
3. (a) Cossío, F. P.; Arrieta, A.; Cebolla, V. L.; Membrado, L.; Domingo, M. P.; Henrion, P.; Vela, J. Anal. Chem. 2000, 72, 1759-1766.
4. (b) Cebolla, V. L.; Membrado, L.; Domingo, M. P.; Henrion, P.; Garriga, R.; González, P.; Cossío, F. P.; Arrieta, A.; Vela, J. J. Chromatogr. Sci. 1999, 37, 219
5. Although this phenomenon also takes place in solution, the use of silica gel plates provides a rigid support that enhances the fluorescent response and also a chromatographic system to separate the analyte of interest from other components in complex mixtures. Moreover, the signal can be easily quantified using a fluorescence scanning densitometer (in this case, a CS9301 TLC scanner from Shimadzu, Japan).
6. Procedure details can be found in ref 3a. PM3 semiempirical Hamiltonian at the Hartree-Fock (HF) level was used for a complete geometry optimization of the berberine cation. The ion-molecule complex between n-hexane and the berberine cation was optimized at the HF/PM3 level. Finally, geometries of berberine and the berberine-n-hexane complex in the first excited state were optimized at the 3X3CI-HE/PM3 level of theory.
7. Atkins, P. W.; Friedman, R. S. Molecular Quantum Mechanics; Oxford University Press: Oxford, 1997; p 508.
8. Lakowitz, J. R. Principles of Fluorescence Spectroscopy; Plenum Press: New York, 1983; pp 9-11.
9. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; VCH: Wheinheim, 1990; pp 9-13.
10. Chromatographic conditions for Figure 2 were as follows: applied volume, 0.4 μL; impregnation conditions, 4 mg of berberine sulfate in 200 mL of methanol during 20 s; elution, n-hexane (9-min). Fluorescent scanning densitometry after excitation at 365 nm was performed (1 × 1 mm beam size), and emission was collected in the 450-550 nm zone. The corresponding polarizabilities for the alkanes were calculated from Clausius-Mossotti equation (Debye, P. Polar Molecules; Dover Publications, 1929; p 11). Data were obtained from TRC database (Texas A&M Universiry).