A new series of proton/charge transfer molecules: Synthesis and spectral studies of 2-(5-Aryl-1-carbomethoxy-1H-pyrazol-3-yl)phenols

Photochemistry and Photobiology

Volumn 70, Issue 2, 1999, Pages 176-183

  Rampey, Mary E ^a   Halkyard, Carrie E ^a   Williams, Angela R ^a   Angel, April J ^a   Hurst, Douglas R ^a   Townsend, Jessica D ^a   Finefrock, Anne E ^a   Beam, Charles F ^a   Studer Martinez, Shannon L ^a  

^a School of Business and Economics   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000648983     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1999.tb07987.x     Document Type: Article

References (40)

1. Kasha, M. (1986) Proton-transfer spectroscopy. Perturbation of the tautomerization potential. J. Chem. Soc. Faraday Trans. II 82, 2379-2392.
2. Barbara, P. F., P. K. Walsh and L. E. Brus (1989) Picosecond kinetic and vibrationally resolved spectroscopic studies of intramolecular excited-state hydrogen atom transfer. J. Phys. Chem. 93, 29-34.
3. Barbara, P. F. and H. D. Trommsdorff (eds.) (1989) Special issue (Spectroscopy and dynamics of elementary proton transfer in polyatomic systems). Chem. Phys. 136, 153-360.
4. Kasha, M., J. Heldt and D. Gormin (1995) Triplet state potentials in the competitive excitation mechanisms of intramolecular proton transfer. J. Phys. Chem. 99, 7281-7284.
5. Catalan, J., F. Fabero, R. M. Claramunt, M. D. Santa Maria, M. de la Concepcion Foces-Foces. F. H. Cano, M. Martinez-Ripoll, J. Elguero and R. Sastre (1992) New ultraviolet stabilizers: 3- and 5-(2′-hydroxyphenyl)pyrazoles. J. Am. Chem. Soc. 114, 5039-5048.
6. Catalan, J., J. Palomar and J. L. G. de Paz (1997) Intramolecular proton or hydrogen-atom transfer in the ground and excited states of 2-hydroxybenzoyl compounds. J. Phys. Chem. A 101, 7914-7921.
7. Simon, J. D. (1988) Time-resolved studies of solvation in polar media. Acc. Chem. Res. 21, 128-134.
8. Barbara, P. F. and W. Jarzeba (1990) Ultrafast photochemical intramolecular charge transfer and excited state solvation. Adv. Photochem. 15, 1-68.
9. Maroncelli, M., J. MacInnis and G. R. Fleming (1989) Polar solvent dynamics and electron-transfer reactions. Science 243, 1674-1681.
10. Lippert, E., W. Rettig, V. Bonacic-Koutecky, F. Heisel and J. A. Miehe (1987) Photophysics of internal twisting. Adv. Chem. Phys. 68, 1-173.
11. Gray, H. B. and J. R. Winkler (1996) Electron transfer in proteins. Annu. Rev. Biochem. 65, 537-561.
12. Chou, P. T., M. L. Martinez and J. H. Clements (1993) The observation of solvent-dependent proton-transfer/charge-transfer lasers from 4′-diethylamino-3-hydroxyflavone. Chem. Phys. Lett. 104, 395-399.
13. Chou, P. T. and M. L. Martinez (1993) Reinvestigation of the photophysics of 2-(2′-hydroxy-4′-diethylaminophenyl)benzothiazole. Photochem. Photobiol. 57, 593-596.
14. Cornelissen-Gude, C. and W. Rettig (1998) Dual fluorescence and multiple charge transfer nature in derivatives of N-pyrrolobenzonitrile. J. Phys. Chem. A 102, 7754-7760.
15. Chou, P. T., M. L. Martinez and J. H. Clements (1993) Reversal of excitation behavior of proton-transfer vs. charge-transfer by dielectric perturbation of electronic manifolds. J. Phys. Chem. 97, 2618-2622.
16. Swinney, T. C. and D. F. Kelley (1993) Proton transfer dynamics in substituted 3-hydroxyflavones: solvent polarization effects. J. Chem. Phys. 99, 211-221.
17. Ormson, S. M., R. G. Brown, F. Vollmer and W. Rettig (1994) Switching between charge- and proton-transfer emission in the excited state of a substituted 3-hydroxyflavone. J. Photochem. Photobiol. A Chem. 81, 65-72.
18. Chou, P. T., D. McMorrow, T. J. Aartsma and M. Kasha (1984) The proton-transfer laser. Gain spectrum and amplification of spontaneous emission of 3-hydroxyflavone. J. Phys. Chem. 88, 4596-4599.
19. Chou, P. T. and T. J. Aartsma (1986) The proton-transfer laser. Dual wavelength lasing action in binary dye mixtures involving 3-hydroxyflavone. J. Phys. Chem. 90, 721-723.
20. Catalan, J., E. Mena, F. Fabero and F. Amat-Guerri (1992) The role of the torsion of the phenyl moiety in the mechanism of stimulated ultraviolet light generation in 2-phenylbenzazoles. J. Chem. Phys. 96, 2005-2016.
21. Acuna, A. U., A. Costela and J. M. Munoz (1986) A proton-transfer laser. J. Phys. Chem. 90, 2807-2808.
22. Chou, P. T., S. L. Studer and M. L. Martinez (1991) Practical and convenient 355 nm and 337 nm sharp-cut filters for multi-channel Raman spectroscopy. Appl. Spectrosc. 45, 513-515.
23. Ernsting, N. P. and B. Nikolaus (1986) Dye laser pulse shortening by transient absorption following excited-state intramolecular proton transfer. Appl. Phys. B 39, 155-164.
24. Renschler, C. L. and L. A. Harrah (1985) Reduction of reabsorption effects in scintillators by using solutes with large Stokes shifts. Nuclear Inst. Methods A 235; U.S. Patent 636655 ChemiAbstr. 103, 185647.
25. Sytnik, A. and M. Kasha (1994) Excited-state intramolecular proton transfer as a fluorescence probe for protein bind-site static polarity. Proc. Natl. Acad. Sci. USA 91, 8627-8630.
26. Haroutounian, S. A. and J. A. Katzenellenbogen (1988) Hydroxystilbazoles and hydroxyazaphenanthrenes: photocyclization and fluorescence studies. Photochem. Photobiol. 47, 503-516.
27. Anstead, G. M., K. E. Carlson, P. R. Kym, K. J. Hwang and J. A. Katzenellenbogen (1993) The effect of acceptor group variation on the solvatochromism of donor-acceptor fluorophores. Photochem. Photobiol. 58, 785-794.
28. Katzenellenbogen, J. A. (1995) The development of molecular probes for fluorescence assay, tumor imaging, and structural studies of steroid receptors. Med. Chem. Res. 5, 606-617.
29. Haroutounian, S. A. and J. A. Katzenellenbogen (1995) 4′-Hydroxystyryldiazines - synthesis and fluorescence properties. Tetrahedron 51, 1585-1598.
30. Diwu, Z., Y. Lu, C. Zhan, D. H. Klaubert and R. P. Haugland (1997) Fluorescent molecular probes II. The synthesis, spectral properties and use of fluorescent solvatochromic Dapoxyl dyes. Photochem. Photobiol. 66, 424-431.
31. French, K. L., A. J. Angel, A. R. Williams, D. R. Hurst and C. F. Beam (1998) A new preparation of substituted 4H-1-benzothiopyran-4-ones from C(α), N-benzoylhydrazones or C(α) N-carboalkoxyhydrazones and methyl thiosalicylate. J. Heterocycl. Chem. 35, 45-48.
32. Demas, J. N. and G. A. Crosby (1971) The measurement of photoluminescence quantum yields. A review. J. Phys. Chem. 75, 991-1024.
33. Hanson, K. M., L. Bulang and J. D. Simon (1997) A spectroscopic study of the epidermal ultraviolet chromophore transurocanic acid. J. Am. Chem. Soc. 119, 2715-2721.
34. Church, A. C., M. U. Koller, M. A. Hines and C. F. Beam (1996) The preparation of 1H-pyrazole-1-carboxylic acid, 1,1-dimethylethyl esters from dilithiated C(α),N-hydrazones of hydrazinecarboxylic acid, 1,1-dimethylethyl ester. Synth. Commun. 26, 3659-3669.
35. Ahamad, R., M. Zai-ul-Haq, N. Khan and N. Kausar (1996) Regioselective cyclocondensation reactions leading to phenolic pyrazoles. Arabian J. Sci. Eng. 21, 393-401.
36. Sharma, T. C., S. R. Pawar and N. J. Reddy (1983) Synthesis of some isomeric pyrazoles. Acta Chim. Hung. 112, 159-162.
37. Colotta, V., D. Catarzi, F. Varno, F. Fabrizio, G. Filacchiani, L. Checchi, A. Galli and C. Costagali (1996) Benzodiazepine binding activity of some tricyclic heteroaromatic systems to define the hydrogen bonding strength of proton donors of the receptors site. Farmaco 51, 223-229.
38. Murthy, A. K., K. S. R. K. M. Rao and N. V. S. Rao (1968) Isoxazolylphenols and their absorption spectra. Aust. J. Chem. 21, 2315-2317.
39. Martinez, M. L., W. C. Cooper and P. T. Chou (1992) A novel excited-state intramolecular proton transfer molecule, 10-hydroxybenzo[h]quinoline. Chem. Phys. Lett. 193, 151-154.
40. Kumar, G. A. and M. A. McAllister (1998) Theoretical investigation of the relationship between proton NMR chemical shift and hydrogen bond strength. J. Org. Chem. 63, 6968-6972.