Comprehensive Photokinetic and NMR Study of a Biphotochromic Supermolecule Involving Two Naphthopyrans Linked to a Central Thiophene Unit Through Acetylenic Bonds

Photochemistry and Photobiology

Volumn 78, Issue 6, 2003, Pages 558-566

  Ortica, Fausto ^a   Moustrou, Corinne ^b   Berthet, Jérôme ^c   Favaro, Gianna ^a   Samat, André ^b   Guglielmetti, Robert ^b   Vermeersch, Gaston ^c   Mazzucato, Ugo ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

^b AIX MARSEILLE UNIVERSITY   (France)

^c UNIV LILLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; NAPHTHOPYRAN DERIVATIVE; PYRAN DERIVATIVE; THIOPHENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; CONCENTRATION RESPONSE; IRRADIATION; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; RADIATION; SPECTROPHOTOMETRY; STEREOISOMERISM;

ACETYLENE; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; PYRANS; SPECTRUM ANALYSIS; THIOPHENES;

EID: 0347761657     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/0031-8655(2003)078<0558:CPANSO>2.0.CO;2     Document Type: Article

References (37)

1. Crano, J. C. and R. J. Guglielmetti (1999) Organic Photochromic and Thermochromic Compounds, Vol. I-II. Kluwer Academic/Plenum Publishers, New York.
2. Dürr, H. and H. Bouas-Laurent (1990) Photochromism: Molecules and Systems. Elsevier, Amsterdam.
3. Ortica, F., D. Levi, P. Brun, R. Guglielmetti, G. Favaro and U. Mazzucato (2001) Photobehaviour of Z-1,2-di-(3′-methoxynaphth-2′ -yl)ethene as model compound of biphotochromic supermolecules with Z-ethenic bridge. Int. J. Photoen. 3, 153-160.
4. Ortica, F., U. Mazzucato, G. Favaro, D. Levi, P. Brun and R. Guglielmetti (2001) Photokinetic behaviour of biphotochromic supramolecular systems Part 2. A bis-benzo-[2H]-chromene and a spirooxazine-chromene with a (Z-) ethenic bridge between each moiety. J. Photochem. Photobiol. A: Chem. 139, 133-141.
5. Favaro, G., D. Levi, F. Ortica, A. Samat, R. Guglielmetti and U. Mazzucato (2002) Photokinetic behaviour of biphotochromic supramolecular systems Part 3. Compounds with chromene and spirooxazine units linked through ethane, ester and acetylene bridges. J. Photochem. Photobiol. A: Chem. 149, 91-100.
6. Berthet, J., S. Delbaere, V. Lokshin, C. Bochu, A. Samat, R. Guglielmetti and G. Vermeersch (2002) Studies of polyphotochromic behaviour of supermolecules by NMR spectroscopy. Part 1. A bisspirooxazine with a (Z) -ethenic bridge between each moiety. Photochem. Photobiol. Sci. 1, 333-339.
7. Berthet, J., S. Delbaere, D. Levi, A. Samat, R. Guglielmetti and G. Vermeersch (2002) Studies of polyphotochromic behaviour of super-molecules by NMR spectroscopy. Part 2. A bis-[3H]naphthopyran with a (Z)-ethenic bridge between each moiety. Photochem. Photobiol. Sci. 1, 665-672.
8. Berthet, J., S. Delbaere, D. Levi, P. Brun, R. Guglielmetti and G. Vermeersch (2002) Investigations by NMR spectroscopy of a polyphotochromic system involving two entities, spirooxazine and naphthopyran, linked by a Z-ethenic bridge. J. Chem. Soc. Perkin Trans. 2 2118-2124.
9. Frigoli, M. (2001) Synthèse et étude des prietes photochromiques de [3H]-naphtopyranes liés à des oligothiophénes au à des groupements aromatiques; Relations structure/prorietés. Thèse de Doctorat, Université de la Méditerranée, Marseille, France.
10. Frigoli, M., C. Moustrou, A. Samat and R. Guglielmetti (2000) Photomodulable materials. Synthesis and properties of photochromic 3H-naphtho[2,1-b]pyrans linked to thiophene units via an acetylenic junction. Helv. Chim. Acta 83, 3043-3052.
11. Coen, S., C. Moustrou, M. Frigoli, M. Julliard, A. Samat and R. Guglielmetti (2001) Spectroscopic properties of thiophene linked [2H]-chromenes. J. Photochem. Photobiol. A: Chem. 139, 1-4.
12. Bartocci, G., F. Masetti, U. Mazzucato, A. Spalletti, I. Baraldi and F. Momicchioli (1987) Photophysical and theoretical studies of photoisomerism and rotamerism of trans-styrylphenanthrenes. J. Phys. Chem. 91, 4733-4743.
13. Murov, S. L., I. Carmichael and G. L. Hug (1993) Handbook of Photochemistry. Marcel Dekker Inc., New York.
14. Kumar, C. V., L. Qin and P. K. Das (1984) Aromatic thioketone triplets and their quenching behaviour towards oxygen and di-t-butylnitroxy radical. J. Chem. Soc. Faraday Trans. 2 80, 783-793.
15. Delbaere, S., J.-C. Micheau, Y. Teral, C. Bochu, M. Campredon and G. Vermeersch (2001) NMR structural and kinetic assignment of fluoro-3H-naphthopyran photomerocyanines. Photochem. Photobiol. 74, 694-699.
16. Pimienta, V., D. Lavabre, G. Levy, A. Samat, R. Guglielmetti and J. C. Micheau (1996) Kinetic analysis of photochromic systems under continuous irradiation. Application to spiropyrans. J. Phys. Chem. 100, 4485-4490.
17. Ottavi, G., F. Ortica and G. Favaro (1999) Photokinetic methods: a mathematical analysis of the rate equations in photochromic systems. Int. J. Chem. Kin. 31, 303-313.
18. Favaro, G., A. Romani and R. S. Becker (2000) Photochromic behavior of 2,2-spiro-adamantylidene-2H-naphtho[1,2-b]pyran: a new thermoreversible and photoreversible photochromic system. Photochem. Photobiol. 72, 632-638.
19. Ortica, F. and G. Favaro (2000) Effect of gel trapping on spectral properties and relaxation dynamics of some spiro-oxazines. J. Phys. Chem. B 104, 12179-12183.
20. Masetti, F., G. Bartocci, U. Mazzucato and E. Fischer (1983) Absorption and emission anomalies in solutions of trans-azastilbenes and related compounds possibly caused by association. J. Chem. Soc., Perkin Trans. 2 797-802.
21. Nakamura, S., K. Uchida, A. Murakami and M. Irie (1993) Ab initio MO and proton NMR NOE studies of photochromic spironaphthoxazine. J. Org. Chem. 58, 5543-5545.
22. Delbaere, S., C. Bochu, N. Azaroual, G. Buntinx and G. Vermeersch (1997) NMR studies of the structure of the photoinduced forms of photochromic spironaphthoxazines. J. Chem. Soc., Perkin Trans. 2 1499-1502.
23. Delbaere, S., B. Luccioni-Houze, C. Bochu, Y. Teral, M. Campredon and G. Vermeersch (1998) Kinetic and structural studies of the photochromic process of 3H-naphthopyrans by UV and NMR spectroscopy. J. Chem. Soc., Perkin Trans. 2 1153-1158.
24. 1H NMR investigation of self-association of aromatic drug molecules in aqueous solution. Structural and thermodynamical analysis. J. Chem. Soc., Faraday Trans. 92, 383-390.
25. Romani, A., G. Favaro and F. Masetti (1995) Luminescence properties of camphorquinone at room temperature. J. Luminesc. 63, 183-188.
26. Van Gemert, B. (1998) Benzo and naphthopyrans (chromenes). In Organic Photochromic and Thermochromic Compounds, Vol. I (Edited by J. C. Crano and R. J. Guglielmetti), pp. 111-139. Kluwer Academic/ Plenum Publishers, New York.
27. Ottavi, G., G. Favaro and V. Malatesta (1998) Spectrokinetic study of 2,2-diphenyl-5,6-benzo(2H)chromene: a thermoreversible and photoreversible photochromic system. J. Photochem. Photobiol. A: Chem. 115, 123-128.
28. Görner, H. and A. K. Chibisov (2002) Photoprocess in 2,2-diphenyl-5,6-benzo(2H)chromene. J. Photochem. Photobiol. A: Chem. 149, 83-89.
29. Favaro, G., U. Mazzucato, G. Ottavi and R. S. Becker (1997) Kinetic analysis of the photochromic behavior of a naturally occurring chromene (lapachenole) under steady irradiation. Mol. Cryst. Liq. Cryst. 298, 137-144.
30. Hobley, J., V. Malatesta, R. Millini, W. Giroldini, L. Wis, M. Goto, M. Kishimoto and H. Fukumura (2000) Photochromism of chromene crystals; a new property of old chromenes. Chem. Commun. 1339-1340.
31. Hobley, J., V. Malatesta, K. Hatanaka, S. Kajimoto, S. C. Williams and H. Fukumura (2002) Picosecond and nanosecond photodynamics of a naphthopyran merocyanine. Phys. Chem. Chem. Phys. 4, 180-184.
32. Aubard, J., F. Maurel, G. Buntinx, O. Poizat, G. Levi, R. Guglielmetti and A. Samat (2000) Femto/pico transient absorption spectroscopy of photochromic 3,3-diphenylnaphtho[2,1-b]pyran. Mol. Cryst. Liq. Cryst. 345, 215-220.
33. Delbaere, S. and G. Vermeersch (2003) NMR proofs of the involvement of an allenyl-naphthol as a key-intermediate in the photochromic process of [3H]-naphthopyrans. Tetrahedron. Lett. 259-262.
34. Becker, R. S., E. Dolan and D. E. Balke (1969) Vibronic effects in photochemistry. Competition between internal conversion and photochemistry. J. Chem. Phys. 50, 239-245.
35. Kholmanskii, A. S. (1983) The role of vibrational excitation in the photochromic reaction of spironaphthopyrans. Russian J. Phys. Chem. 57, 413-416.
36. Favaro, G., A. Romani and R. S. Becker (2001) Competition between vibrational relaxation and photochemistry: relevance of vibronic quantum effects. Photochem. Photobiol. 74, 378-384.
37. Becker, R. S., A. P. Pelliccioli, A. Romani and G. Favaro (1999) Vibronic quantum effects in fluorescence and photochemistry. Competition between vibrational relaxation and photochemistry and consequences on photochemical control. J. Am. Chem. Soc. 121, 2104-2109.