Positional effects of the hydroxy substituent on the photochemical and photophysical behavior of 3- and 4-hydroxystilbene

Photochemical and Photobiological Sciences

Volumn 3, Issue 7, 2004, Pages 660-668

  Crompton, Elizabeth M ^a   Lewis, Frederick D ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONAL GROUP; HYDROXYL GROUP; ORGANIC SOLVENT; PROTON; STILBENE DERIVATIVE;

ABSORPTION SPECTROSCOPY; ACID BASE BALANCE; AQUEOUS SOLUTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CIS TRANS ISOMERISM; CONTROLLED STUDY; EXCITATION; HYDROGEN BOND; MOLECULAR INTERACTION; PHOTOCHEMISTRY; PHOTOREACTIVITY; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTON TRANSPORT; QUANTUM YIELD; RADIATION ABSORPTION; SOLVENT EFFECT; SPECTRAL SENSITIVITY; STRUCTURE ANALYSIS;

EID: 4344651162     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b403661a     Document Type: Article

References (57)

1. E. Havinga R. O. de Jongh W. Dorst Photochemical acceleration of the hydrolysis of nitrophenyl phosphates and nitrophenyl sulfates Recl. Trav. Chim. Pays-Bas 1956 75 378-383.
2. H. E. Zimmerman V. R. Sandel Mechanistic organic photochemistry. II. Solvolytic photochemical reactions J. Am. Chem. Soc. 1963 85 915-922.
3. H. E. Zimmerman Meta-ortho effect in organic photochemistry: Mechanistic and exploratory organic photochemistry J. Phys. Chem. A 1998 102 5616-5621 and references therein.
4. E. L. Wehry L. B. Rogers Application of linear free energy relations to electronically excited states of monosubstituted phenols J. Am. Chem. Soc. 1965 87 4234-4238.
5. 1 states. The influence of substituent orientation J. Phys. Chem. 1981 85 4068-4071.
6. N. Agmon W. Rettig C. Groth Electronic determination of photoacidity in cyanonaphthols J. Am. Chem. Soc. 2002 124 1089-1096.
7. F. D. Lewis R. S. Kalgutkar J.-S. Yang The photochemistry of trans-ortho-, meta-, and para-aminostilbenes J. Am. Chem. Soc. 1999 121 12045-12053.
8. F. D. Lewis W. Weigel Excited state properties of donor-acceptor substituted trans-stilbenes: The meta-amino effect J. Phys. Chem. A 2000 104 8146-8153.
9. F. D. Lewis J.-S. Yang The excited state behavior of aminostilbenes. A new example of the meta effect J. Am. Chem. Soc. 1997 119 3834-3835.
10. H. Güsten L. Klasinc Quantum yields of the photochemical cis-trans isomerization of monosubstituted stilbenes Tetrahedron Lett. 1968 9 3097-3101.
11. R. Lapouyade A. Kuhn J.-F. Letard W. Rettig Multiple relaxation pathways in photoexcited dimethylaminonitro- and dimethylaminocyano-stilbenes Chem. Phys. Lett. 1993 208 48-58.
12. D. H. Waldek Photoisomerization dynamics of stilbenes Chem. Rev. 1991 91 415-436.
13. J. Saltiel and J. L. Charlton, in Rearrangements in Ground and Excited States, ed. P. de Mayo, Academic Press, New York, 1980.
14. D. H. McDaniel H. C. Brown An extended table of Hammett substituent constants based on the ionization of substituted benzoic acids J. Org.Chem. 1958 23 420-427.
15. H. C. Brown Y. Okamoto Electrophilic substituent constants J. Am. Chem. Soc. 1958 80 4979-4987.
16. J. Saltiel A. S. Waller D. F. Sears The temperature and medium dependencies of cis-stilbene fluorescence. The energetics of twisting in the lowest excited singlet state J. Am. Chem. Soc. 1993 115 2453-2465.
17. J. N. Murrell, The Theory of the Electronic Spectra of Organic Molecules, John Wiley & Sons, Inc., New York, 1963.
18. I. G. Binev R. B. Kuzmanova J. Kaneti I. N. Juchnovski Determination of constants of anionic substituents based on nitrile infrared frequencies and intensities J. Chem. Soc., Perkin Trans. 2 1982 1533-1536.
19. F. D. Lewis E. M. Crompton Hydroxystilbene isomer-specific photoisomerization versus proton transfer J. Am. Chem. Soc. 2003 125 4044-4045.
20. T. Murohoshi K. Kaneda M. Ikegami T. Arai Photoisomerization and isomer-specific addition of water in hydroxystilbenes Photochem. Photobiol. Sci. 2003 2 1247-1249.
21. B. H. Lee C. S. Marvel New processable polyaromatic ether-keto-sulfones as colorless, clear film-forming materials J. Polym. Sci., Polym. Chem. Ed. 1982 20 393-399.
22. M. A. Ali K. Kondo Y. Tsuda Synthesis and nematocidal activity of hydroxystilbenes Chem. Pharm. Bull. 1992 40 1130-1136.
23. I. B. Berlman, Handbook of Fluorescence Spectra of Aromatic Molecules, Academic Press, New York, 1971.
24. M. Sczepan W. Rettig A. I. Tolmachev V. V. Kurdyukov The role of internal twisting in the photophysics of stilbazolium dyes Phys. Chem. Chem. Phys. 2001 3 3555-3561.
25. Grams/32, Galactic Industries Corp., Salem, NH 03079, 1997.
26. M. C. Zerner G. H. Loew R. F. Kirchner U. T. Mueller-Westerhoff An intermediate neglect of differential overlap technique for spectroscopy of transition-metal complexes. Ferrocene J. Am. Chem. Soc. 1980 102 589-599.
27. CAChe, Fujitsu Limited, Chiba, Japan, 2000.
28. A. Albert and E. P. Serjeant, in The Determination of Ionization Constants, a Laboratory Manual, Chapman and Hall, New York, 1984.
29. T. Förster Elektrolytische dissoziation angeregter moleküle Z. Elektrochem. 1950 54 42-46.
30. A. Weller Fast reactions of excited molecules Prog. React. Kinet. 1961 1 187-214.
31. I. Y. Martynov A. B. Demyashkevich B. M. Uzhinov M. G. Kuz’min Proton transfer reactions in the excited electronic states of aromatic molecules Russ. Chem. Rev. Usp. Khim. 1977 46 1-15.
32. V. V. Volkov Separation of additive mixture spectra by a self-modeling method Appl. Spectrosc. 1996 50 320-326.
33. Mathematica, Wolfram Research, Inc., Champaign, IL 61820, 1999.
34. Matlab, The Mathworks, Inc., Natick, MA 01760, 1999.
35. J. F. Ireland P. A. H. Wyatt Acid–base properties of electronically excited states of organic molecules Adv. Phys. Org. Chem. 1976 12 131-221.
36. A. Weller Quantitative untersuchungen der fluorszenzumwandlung bei naphtholen Z. Elektrochem. 1952 56 662-668.
37. S. G. Schulman Acid–base chemistry of excited singlet states. Fundamentals and analytical implications Mod. Fluoresc. Spectrosc. 1976 2 239-275.
38. G. Granucci J. T. Hynes P. Millié T.-H. Tran-Thi A theoretical investigation of excited-state acidity of phenol and cyano-phenols J. Am. Chem. Soc. 2000 122 12243-12253.
39. M. J. Kamlet J. L. M. Abboud M. H. Abraham R. W. Taft Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, π*, α, and β, and some methods for simplifying the generalized solvatochromic equation J. Org. Chem. 1983 48 2877-2887.
40. J. Saltiel A. Marinari D. W.-L. Chang J. C. Mitchener E. D. Megarity Trans-cis photoisomerization of the stilbenes and a reexamination of the positional dependence of the heavy-atom effect J. Am. Chem. Soc. 1979 101 2982-2996.
41. S. K. Kim S. H. Courtney G. R. Fleming Isomerization of t-stilbene in alcohols Chem. Phys. Lett. 1989 159 543-548.
42. A. Weller Protolytische reaktionen angeregter oxyverbindungen Z. Phys. Chem. (Munich) 1958 17 224-245.
43. J. P. Soumillion P. Vandereecken M. van der Auweraer F. C. de Schryver A. Schanck Photophysical analysis of ion pairing of β-naphtholate in medium polarity solvents: Mixtures of contact and solvent-separated ion pairs J. Am. Chem. Soc. 1989 111 2217-2225.
44. E. Lippert Spectroscopic determination of the dipole moment of aromatic compounds in the first excited singlet state Z. Elektrochem. 1957 61 962-975.
45. N. Mataga Y. Kaifu M. Koizumi Solvent effects upon fluorescence spectra and the dipole moments of excited molecules Bull. Chem. Soc. Japan 1956 29 465-470.
46. W. Liptay Solvent-dependence of the wave number of electron bands and physicochemical fundamentals Z. Naturforsch. 1965 20a 1441-1471.
47. P. Suppan and N. Ghoneim, Solvatochromism, The Royal Society of Chemistry, Cambridge, UK, 1997.
48. K. M. Solntsev D. Huppert N. Agmon Solvatochromism of β-naphthol J. Phys. Chem. A 1998 102 9599-9606.
49. K. M. Solntsev D. Huppert L. M. Tolbert N. Agmon Solvatochromic shifts of “super” photoacids J. Am. Chem. Soc. 1998 120 7981-7982.
50. K. M. Solntsev D. Huppert N. Agmon Photochemistry of “super”-photoacids. Solvent effects J. Phys. Chem. A 1999 103 6984-6997.
51. L. M. Tolbert K. M. Solntsev Excited-state proton transfer: From constrained systems to “super” photoacids to superfast proton transfer Acc. Chem. Res. 2002 35 19-27.
52. Z. R. Grabowski A. Grabowska The Förster cycle reconsidered Z. Phys. Chem. (Munich) 1976 101 197-208.
53. E. Pines D. Huppert N. Agmon Geminate recombination in excited state proton transfer reactions: Picosecond dynamics in electrolyte solutions Springer Ser. Chem. Phys. 1988 48 517-519.
54. L. G. Arnaut S. J. Formosinho Excited-state proton transfer reactions. I. Fundamentals and intermolecular reactions J. Photochem. Photobiol., A 1993 75 1-20.
55. M. J. van der Meer H. Zhang W. Rettig M. Glasbeek Femto- and picosecond fluorescence studies of solvation and non-radiative deactivation of ionic styryl dyes in liquid solution Chem. Phys. Lett. 2000 320 673-680.
56. H. Fidder M. Rini E. T. J. Nibbering The role of large conformational changes in efficient ultrafast internal conversion: Deviations from the energy gap law J. Am. Chem. Soc. 2004 126 3789-3794.
57. J. Michl and V. Bonacic-Koutecký, Electronic Aspects of Organic Photochemistry, John Wiley & Sons, New York, 1990.