Synthesis and characterization of azobenzene-confined porphyrins

Journal of Organic Chemistry

Volumn 71, Issue 20, 2006, Pages 7846-7849

  Peters, Maike V ^a   Goddard, Richard ^a   Hecht, Stefan ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ISOMERIZATION; ORGANIC COMPOUNDS; PHOTOCHROMISM; REACTION KINETICS; SYNTHESIS (CHEMICAL);

PHOTOISOMERIZATION; SYNTHETIC METHOD; TETRAPHENYLPORPHYRIN;

PORPHYRINS;

AZOBENZENE DERIVATIVE; PORPHYRIN DERIVATIVE;

ABSORPTION SPECTROPHOTOMETRY; ARTICLE; CHEMICAL STRUCTURE; FLUORESCENCE RESONANCE ENERGY TRANSFER; ISOMERISM; MOLECULAR MODEL; STIMULUS RESPONSE; SYNTHESIS;

EID: 33749143178     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0612877     Document Type: Article

References (34)

1. (a) Photochromism - Molecules and Systems; Dürr, H., Bouas-Laurent H., Eds.; Elsevier: Amsterdam, 2003.
2. (b) Molecular Switches; Feringa, B. L., Ed.; Wiley-VCH: Weinheim, 2001.
3. (c) Organic Photochromic and Thermochromic Compounds; Crano, J. C., Guglielmetti, R. J., Eds.; Kluwer Academic/Plenum Publishers: New York, 1999.
4. (d) Organic Photochromes; El'tsov, A. V., Ed.; Consultants Bureau: New York, 1990.
5. (e) Special Issue: Photochromism: Memories and Switches. Irie, M., Ed. Chem. Rev. 2000, 100, 1683-1890.
6. (f) Hecht, S. Small 2005, 1, 26-29.
7. (a) Ueno, A.; Takahashi, K.; Osa, T. J. Chem. Soc., Chem. Commun. 1981, 94-96.
8. (b) Würthner, F.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1995, 34, 446-448.
9. (c) Würthner, F.; Rebek, J., Jr. J. Chem. Soc. Perkin Trans. 2 1995, 1727-1734.
10. (d) Cacciapaglia, R.; Di Stefano, S.; Mandolini, L. J. Am. Chem. Soc. 2003, 125, 2224-2227.
11. (e) Sud, D.; Norsten, T. B.; Branda, N. R. Angew. Chem., Int. Ed. 2005, 44, 2019-2021.
12. The Porphyrin Handbook; Radish, K., Smith, K. M., Guilard, R., Eds.; Academic Press: New York, 1999.
13. Milgrom, L. R. The Colors of Life; Oxford University Press: New York, 1997.
14. An alternative supramolecular approach based on E-Z-photoisomerization of a stilbene-type pyridine ligand leads to photomodulation of axial ligation in aluminum porphyrins and hence catalytic activity in the copolymerization of carbon dioxide and ethylene oxide: Sugimoto, H.; Kimura, T.; Inoue, S. J. Am. Chem. Soc. 1999, 121, 2325-2326.
15. (a) Hombrecher, H. K.; Lüdtke, K. Tetrahedron 1993, 49, 9489-9494.
16. (b) Autret, M.; Le Plouzennec M.; Moinet, C.; Simonneaux, G. J. Chem. Soc., Chem. Commun. 1994, 1169-1170.
17. (c) Hunter, C. A.; Sarson, L. D. Tetrahedron Lett. 1996, 37, 699-702.
18. (d) Tsuchiya, S. J. Am. Chem. Soc. 1999, 121, 48.
19. (a) Neumann, K. H.; Vögtle, F. J. Chem. Soc., Chem. Commun. 1988, 520-522.
20. (b) Yamara, T.; Momotake, A.; Arai, T. Tetrahedron Lett. 2004, 45, 9219-9223.
21. Otsuki, J.; Harada, K.; Araki, K. Chem. Lett. 1999, 28, 269-270.
22. (b) Reddy, D. R.; Maiya, B. G. Chem. Commun. 2001, 117-118.
23. (c) Reddy, D. R.; Maiya, B. G. J. Phys. Chem. A 2003, 107, 6326-6333.
24. Ito, Y.; Ito, H.; Matsuura, Y. Tetrahedron Lett. 1988, 29, 563-566.
25. Peters, M. V.; Stoll, R. S.; Goddard, R.; Buth, G.; Hecht, S. J. Org. Chem. 2006, 71, 7840-7845.
26. Lee, C.-H.; Lindsey, J. S. Tetrahedron 1994, 50, 11427-11440.
27. Milanese, M. E.; Morán, F. S.; Yslas, E. I.; Alvarez, M. G.; Rivarola, V.; Durantini, E. Bioorg. Med. Chem. 2001, 9, 1943-1949.
28. This useful protocol for azobenzene formation has been developed: Lim, Y.-K.; Lee, K.-S.; Cho, C.-G. Org. Lett. 2003, 5, 979-982.
29. Only in THF photochemistry was observed, giving rise to irreversible production of as yet unidentified photoproducts.
30. Due to experimental reasons, i.e., spectral overlap with the overtone band, low emission intensity, and residual porphyrin UV-absorption, the FRET efficiency could not be determined quantitatively.
31. Although azobenzene is not fluorescent at room temperature, its emission spectrum has been determined; see: Fujino, T.; Arzhansev, S. Y.; Tahara, T. J. Phys. Chem. A 2001, 105, 8123-8129. The emission maximum is located around 390 nm, thereby exhibiting significant spectral overlap with the intense zinc porphyrin Soret band.
32. Scholes, G. D. Annu. Rev. Phys. Chem. 2003, 54, 57.
33. Muraoka, T.; Kinbara, K.; Aida, T. Nature (London) 2006, 440, 512-515.
34. Wolters, M.; Klapars, A.; Buchwald, S. L. Org. Lett. 2001, 3, 3803-3805.