The chemistry of 6-hydroxyflavylium: Zwitterionic base and p-quinoidal chalcones. A multiswitchable system operated by proton, electron and photon inputs

Photochemical and Photobiological Sciences

Volumn 6, Issue 4, 2007, Pages 372-380

  Jimenez, Antonio ^a   Pinheiro, Carlos ^b   Jorge Parola, A ^b   Maestri, Mauro ^c   Pina, Fernando ^b  

^a UNIVERSITY OF JAÉN   (Spain)

^b UNIVERSIDADE NOVA DE LISBOA   (Portugal)

^c UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOLYTE; CHALCONE DERIVATIVE; PROTON;

ARTICLE; CHEMICAL REACTION; ELECTROCHEMISTRY; ELECTRON; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY; PHOTON; PRIORITY JOURNAL; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 34047243164     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b615464f     Document Type: Article

References (47)

1. A. Niemz V. M. Rotello From Enzyme to Molecular Device. Exploring the Interdependence of Redox and Molecular Recognition Acc. Chem. Res. 1999 32 44-52.
2. A. E. Kaifer Interplay between Molecular Recognition and Redox Chemistry Acc. Chem. Res. 1999 32 62-71.
3. V. Balzani A. Credi F. M. Raymo J. F. Stoddart Artificial Molecular Machines Angew. Chem., Int. Ed. 2000 39 3348-3391.
4. Molecular Switches, ed. B. L. Feringa, Wiley-VCH, Weinheim, 2001.
5. M. Irie O. Miyatake K. Uchida T. Eriguchi Photochromic Diarylethenes with Intralocking Arms J. Am. Chem. Soc. 1994 116 9894-9900.
6. S. H. Kawai S. L. Gilat R. Posinet J.-M. Lehn A Dual-Mode Molecular Switching Device: Bisphenolic Diarylethenes with Integrated Photochromic and Electrochromic Properties Chem.–Eur. J. 1995 1 285-293.
7. H. Speitzer J. Daub Multi-mode switching based on dihydroazulene/vinylheptafulvene photochromism: Synergism of photochromism and redox switching in heteroaryl-functionalized systems Chem.–Eur. J. 1996 2 1150-1158.
8. H. Plenio C. Aberle An Artificial Regulatory System with Coupled Molecular Switches Angew. Chem., Int. Ed. 1998 37 1397-1399.
9. H.-F. Ji R. Dabestani G. M. Brown A Supramolecular Fluorescent Probe, Activated by Protons To Detect Cesium and Potassium Ions, Mimics the Function of a Logic Gate J. Am. Chem. Soc. 2000 122 9306-9307.
10. A. Goodman E. Breinlinger M. Ober V. M. Rotello Controlled Multi-Stage Recognition of Guests Using Orthogonal Electro- and Photochemical Inputs J. Am. Chem. Soc. 2001 123 6213-6214.
11. L. Gobbi P. Seiler F. Diederich A Novel Three-Way Chromophoric Molecular Switch: pH and Light Controllable Switching Cycles Angew. Chem., Int. Ed. 1999 38 674-678.
12. L. Gobbi P. Seiler F. Diederich V. Gramlich C. Boudon J.-P. Gisselbrecht M. Gross Photoswitchable Tetraethynylethene-Dihydroazulene Chromophores Helv. Chim. Acta 2001 84 743-777.
13. C. Bourgel A. S. F. Boyd G. Cooke H. Augier de Cremiers F. M. A. Duclairoir V. M. Rotello The first redox controlled hydrogen bonded three-pole switch Chem. Commun. 2001 1954-1955.
14. W. Zhao E. M. Carreira A Smart Photochromophore through Synergistic Coupling of Photochromic Subunits J. Am. Chem. Soc. 2002 124 1582-1583.
15. A. P. de Silva H. Q. N. Gunaratne T. Gunnlaugsson A. J. M. Huxley C. P. McCoy J. T. Rademacher T. E. Rice Signaling Recognition Events with Fluorescent Sensors and Switches Chem. Rev. 1997 97 1515-1566.
16. V. Balzani, A. Credi and M. Venturi, Transition Metal-containing Catenanes and Rotaxanes: Control of Electronic and Molecular Motions, in Supramolecular Science: Where It is and Where It is Going, ed. R. Ungaro and E. Dalcanale, Kluwer, Dordrecht, 1999, NATO Science Series C, vol. 527, pp. 1–22.
17. A. P. de Silva, D. B. Fox and T. S. Moody, Luminescent Logic and Sensing, in Stimulating Concepts in Chemistry, ed. F. Vögtle, J. F. Stoddart and M. Shibasaki, Wiley-VCH, Weinheim, 2000, pp. 307–316.
18. A. R. Pease J. F. Stoddart Computing at the Molecular Level Struct. Bonding 2001 99 189-236.
19. A. P. de Silva, N. D. McClenaghan and C. P. McCoy, Molecular Logic Systems, in Molecular Switches, ed. B. L. Feringa, Wiley-VCH, Weinheim, 2001, pp. 339–361.
20. F. M. Raymo Digital Processing and Communication with Molecular Switches Adv. Mater. 2002 14 401-414.
21. H. Lederman J. Macdonald D. Stefanovic M. N. Stojanovic Deoxyribozyme-Based Three-Input Logic Gates and Construction of a Molecular Full Adder Biochemistry 2006 45 1194-1199.
22. About ubiquitous computing and its applications see: www.ubiq.com/hypertext/weiser/calmtech/calmtech.htm.
23. http://ice.chem.wisc.edu/catalogitems/FunStuff.htm.
24. http://www.innovation.rca.ac.uk/archive/pr_sing.php?i=0#.
25. P. Figueiredo J. C. Lima H. Santos M.-C. Wigand R. Brouillard A. Maçanita F. Pina Photochromism of the Synthetic 4′,7-Dihydroxyflavylium Chloride J. Am. Chem. Soc. 1994 116 1249-1254.
26. F. Pina M. Maestri V. Balzani Photochromic flavylium compounds as multistate/multifunction molecular-level systems Chem. Commun. 1999 107-114.
27. M. Maestri, F. Pina and V. Balzani, Multistate/Multifunctional Molecular-Level Systems-Photochromic Flavylium Compounds, in Molecular Switches, ed. L. B. Feringa, Wiley-VCH, Weinheim, 2001, pp. 309–334.
28. J. R. Brouillard J. E. Dubois Mechanism of the structural transformations of anthocyanins in acidic media J. Am. Chem. Soc. 1977 99 1359-1364.
29. R. A. McClelland S. Gedge Hydration of the flavylium ion J. Am. Chem. Soc. 1980 102 5838-5848.
30. R. A. McClelland G. H. McGall Hydration of the flavylium ion. 2. The 4′-hydroxyflavylium ion J. Org. Chem. 1982 47 3730-3736.
31. R. Brouillard, Flavonoids and the flower colour, in The Flavonoids, Advances in Research, ed. J. B. Harborne, Chapman and Hall, London, 1988, pp. 525–538.
32. R. Brouillard, Chemical structure of anthocyanins, in Anthocyanins as Food Colors, ed. P. Markakis, Academic Press, New York, 1982, pp. 1–40.
33. D. Amic D. Davidovic-Amic D. Beslo Prediction of pK Values, Half-Lives, and Electronic Spectra of Flavylium Salts from Molecular Structure J. Chem. Inf. Comput. Sci. 1999 39 967-973 and references therein.
34. F. Pina M. J. Melo A. J. Parola M. Maestri V. Balzani pH-Controlled Photochromism of Hydroxyflavylium ions Chem.–Eur. J. 1998 4 2001-2007.
35. See e.g., M. C. Moncada A. J. Parola C. Lodeiro F. Pina M. Maestri V. Balzani Multistate/Multifunctional Behaviour of 6-nitro-4′-hydroxyflavylium. A Write-lock/Read/Unlock/Enable-erase/Erase Cycle Driven by Light and pH Stimulation Chem.–Eur. J. 2004 10 1519-1526.
36. C. A. Bishop L. K. J. Tong Equilibria of Substituted Semiquinones at High pH J. Am. Chem. Soc. 1965 87 501-505.
37. K. T. Finaly, in The Chemistry of the Quinonoid Compounds, ed. S. Patai, Wiley, NY, 1974, Part 2, ch. 17, p. 942.
38. L. D. Hicks A. J. Fry V. C. Kurzweil Ab initio computation of electron affinities of substituted benzalacetophenones (chalcones): a new approach to substituent effects in organic electrochemistry Electrochim. Acta 2004 50 1039-1047.
39. P. Ferreira da Silva J. C. Lima F. H. Quina A. Maçanita Excited-State Electron Transfer in Anthocyanins and Related Flavylium Salts J. Phys. Chem. A 2004 108 10133-10140.
40. R. Robinson D. D. Pratt CLXXXVIII.—A synthesis of pyrylium salts of anthocyanidin type J. Chem. Soc. Trans. 1922 1577-1585.
41. Ch. Michaelidis R. Wizinger Beitrag zur Kenntnis der 2-Aryl-benzopyryliumsalze Helv. Chim. Acta 1951 34 1761-1770.
42. 2O, acidified with 20% (w/w) DCl, or basified with 40% (w/w) NaOD. The, reported pD values are direct readings of the pH meter which can be corrected for the isotope effect through the equation pD = pH + 0.4.
43. P. K. Glasoe F. A. Long Use of glass electrodes to measure acidities in deuterium oxide J. Phys. Chem. 1960 64 188-190.
44. R. Robinson H. G. Crabtree C. K. Das W. Lawson R. W. Lunt B. H. Roberts P. N. Williams XXVII.—Some derivatives of benzopyrylium J. Chem. Soc. Trans. 1924 207-214.
45. F. W. Küster and A. Thiel, Tabelle per le Analisi Chimiche e Chimico-Fisiche, 12th edn, Hoepli, Milano, 1982, pp. 157–160.
46. M. Maestri R. Ballardini F. Pina M. J. Melo An easy and inexpensive flash spectroscopy experiment J. Chem. Educ. 1997 74 1314-1316.
47. Hyperchem™, release 6.01 for windows, Copyright © Hypercube, Inc., 2000.