Emptying the β-cyclodextrin cavity by light: Photochemical removal of the trans -chalcone of 4′,7-dihydroxyflavylium

Journal of Physical Chemistry A

Volumn 117, Issue 41, 2013, Pages 10692-10701

  Petrov, Vesselin ^a,b   Stanimirov, Stanislav ^a   Petrov, Ivan K ^a   Fernandes, Ana ^c   De Freitas, Victor ^c   Pina, Fernando ^b  

^a UNIVERSITY OF SOFIA   (Bulgaria)

^b UNIVERSIDADE NOVA DE LISBOA   (Portugal)

^c UNIVERSITY OF PORTO   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC MEDIUMS; ASSOCIATION CONSTANT; CHALCONES; CYCLODEXTRIN CAVITIES; FLASH PHOTOLYSIS; INITIAL STATE; STOPPED FLOW; UV-VIS ABSORPTIONS;

POSITIVE IONS;

CYCLODEXTRINS;

EID: 84886876029     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp4060582     Document Type: Article

References (23)

1. Gomes, R.; Albuquerque, R. Q.; Pina, F.; Parola, A. J.; De Cola, L. Supramolecular Host-Guest Flavylium-Loaded Zeolite L Hybrid Materials: Network of Reactions of Encapsulated 7,4-Dihydroxyflavylium Photochem. Photobiol. Sci. 2010, 9, 916-922
2. Pina, F.; Hatton, A. T. Photochromic Soft Materials: Flavylium Compounds Incorporated Into Pluronic F-127 Hydrogel Matrixes Langmuir 2008, 24, 2356-2364
3. Pina, F.; Lima, J. C.; Parola, A. J.; Afonso, C. A. M. Thermal and Photochemical Properties of 4′,7-dihydroxyflavylium in Water-Ionic Liquids Biphasic Systems. A Novel Approach to a Write-Read-Erase Molecular Switching System Angew. Chem., Int. Ed. 2004, 43, 1525-1527
4. Pina, F.; Melo, M. J.; Laia, C. A. T.; Parola, A. J.; Lima, J. C. Chemistry and Applications of Flavylium Compounds: A Handful of Colours Chem. Soc. Rev. 2012, 41, 869-908
5. Pina, F.; Petrov, V.; Laia, C. A. T. Photochromism of Flavylium Systems. An Overview of a Versatile Multistate System Dyes Pigm. 2012, 92, 877-889
6. Magnúsdóttir, A.; Másson, M.; Loftsson, T. Self Association and Cyclodextrin Solubilization of NSAIDs J. Inclusion Phenom. Macrocyclic Chem. 2002, 44, 213-218
7. Loftsson, T.; Jarho, P.; Másson, M.; Järvinen, T. Cyclodextrins in Drug Delivery Expert Opin. Drug Delivery. 2005, 2, 335-351
8. Loftsson, T.; Másson, M.; Brewster, M. E. Self-Association of Cyclodextrins and Cyclodextrin Complexes J. Pharm. Sci. 2004, 93, 1091-1099
9. Figueiredo, P.; Lima, J. C.; Santos, H.; Wigand, M. C.; Brouillard, R.; Maçanita, A. L.; Pina, F. Photochromism of the Synthetic 4′,7-Dihydroxy-Flavylium Chloride J. Am. Chem. Soc. 1994, 116, 1249-1254
10. McClelland, R. A.; Gedge, S. Hydration of the Flavylium Ion J. Am. Chem. Soc. 1980, 102, 5838-5848
11. McClelland, R. A.; McGall, G. H. Hydration of the Flavylium Ion. 2. the 4′-Hydroxyflavylium Ion J. Org. Chem. 1982, 47, 3730-3736
12. Pina, F.; Melo, M. J; Parola, A. J.; Maestri, M.; Balzani, V. pH-Controlled Photochromism of Hydroxyflavylium Ions Chem.-Eur. J. 1998, 4, 2001-2007
13. Brouillard, R.; Dubois, J.-E. Mechanism of the Structural Transformations of Anthocyanins in Acidic Media J. Am. Chem. Soc. 1997, 99, 1359-1364
14. Brouillard, R.; Lang, J. The Hemiacetal-Cis-Chalcone Equilibrium of Malvin, A Natural Anthocyanin Can. J. Chem. 1990, 68, 755-761
15. Petrov, V.; Pina, F. Analytical Resolution of the Reaction Rates of Flavylium Network by Laplace Transform J. Math. Chem. 2010, 47, 1005-1026
16. Dangles, O.; Stoeckel, C.; Wigand, M. C.; Brouillard, R. Two Very Distinct Types of Anthocyanin Complexation: Copigmentation and Inclusion Tetrahedron Lett. 1992, 33, 5227-5230
17. Dangles, O.; Wigand, M. C.; Brouillard, R. Anthocyanin Anti-Copigment Effect Phytochemistry 1992, 31, 3811-3812
18. Fernandes, A.; Sousa, A.; Azevedo, J.; Mateus, N.; Freitas, V. Effect of Cyclodextrins on the Thermodynamic and Kinetic Properties of Cyanidin-3-O-Glucoside Food Res. Int. 2013, 51, 748-755
19. Katritzky, A. R.; Czerney, P.; Levell, J. R.; Du, W. H. Molecular Engineering of Benzo[b]Pyrylium Salts by Indirect Electrophilic Substitution Eur. J. Org. Chem. 1998, 11, 2623-2629
20. Pina, F.; Melo, M. J.; Ballardini, R.; Flamigni, L.; Maestri, M. Flash photolysis of 4′,7′-dihydroxyflavylium New J. Chem. 1997, 21, 969-976
21. Hwang, T. L.; Shaka, A. J. Water Suppression That Works. Excitation Sculpting Using Arbitrary Wave-Forms and Pulsed-Field Gradients J. Magn. Reson., Ser. A 1995, 112, 275-279
22. Popov, K.; Rönkkömäki, H.; Lajunen, L. H. J. Guidelines For NMR Measurements For Determination of High and Low pKa Values Pure Appl. Chem. 2006, 78, 663-675
23. Gomes, R.; Parola, A. J.; Lima, J. C.; Pina, F. Solvent Effects on the Thermal and Photochemical Reactions of 4′-Iodo-8-methoxyflavylium and Their Consequences on the Coloring Phenomena Caused by Anthocyanins in Plants Chem.-Eur. J. 2006, 12, 7906-7912