Synthesis and photophysics of a novel porphyrin-C60 hybrid

Tetrahedron Letters

Volumn 38, Issue 47, 1997, Pages 8133-8136

  Safonov, Igor G ^b   Baran, Phil S ^c   Schuster, David I ^a  

^a NEW YORK UNIVERSITY   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

^c SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIMETHYL SULFOXIDE; FULLERENE; METAL ION; PORPHYRIN; SINGLET OXYGEN;

ARTICLE; COMPLEX FORMATION; DRUG SOLUBILITY; DRUG SYNTHESIS; HYBRID;

EID: 0030663393     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10184-8     Document Type: Article

References (42)

1. Liddell, P.A.; Sumida, J.P.; Macpherson, A.N.; Noss, L; Seely, G.R.; Clark, K.N.; Moore, A.L.; Moore, T.A.; Gust, D. Photochem. Photobiol. 1994, 60, 537.
2. Arbogast, J.W.; Darmanyan, A.P.; Foote, C.S.; Rubin, Y.; Diederich, F.N.; Alvarez, M. M.; Anz, S.; Whetten, R.L. J. Phys. Chem. 1991, 95, 11
3. Bonnett, R. Chem. Soc. Rev. 1995, 24, 19; Jensen, A.W.; Wilson, S.R.; Schuster, D.I. Bioorg. Med. Chem. 1996, 4, 767.
4. Bonnett, R. Chem. Soc. Rev. 1995, 24, 19; Jensen, A.W.; Wilson, S.R.; Schuster, D.I. Bioorg. Med. Chem. 1996, 4, 767.
5. (a) Imahori, H.; Hagiwara, K.; Akiyama, T.; Taniguchi, S.; Okada, T.; Sakata, Y. Chem. Lett. 1995, 265.
6. (b) Drovetskaya, T.; Reed, C.A.; Boyd, P. Tetrahedron Lett. 1995, 36, 7971.
7. (c) Imahori, H.; Sakata, Y. Chem. Lett. 1996, 199.
8. (d) Ranasinghe, M.G.; Oliver, A.M.; Rothenfluh, D.F.; Salek, A.; Paddon-Row, M.N. Tetrahedron Lett. 1996, 37, 4797.
9. (e) Akiyama, T.; Imahori, H.; Ajawakom, A.; Sakata, Y. Chem. Lett. 1996, 907.
10. (f) Imahori, H.; Hagiwara, K.; Aoki, M.; Akiyama, T.; Taniguchi, S.; Okada, T.; Shirakawa, M.; Sakata, Y. J. Am. Chem. Soc. 1996, 118, 11771.
11. (g) Kuciauskas, D.; Lin, S.; Seely, G. R.; Moore, A. L.; Moore, T. A.; Gust, D.; Drovetskaya, T.; Reed, C. A.; Boyd, P. D. W. J. Phys. Chem. 1996, 100, 15926.
12. (h) Liddell, P.A.; Kuciauskas, D.; Sumida, J.P.; Nash, B.; Nguyen, D.; Moore, A.L.; Moore, T.A.; Gust, D. J. Am. Chem. Soc. 1997, 119, 1400.
13. Baran, P.S.; Monaco, R.R.; Khan, AU.; Schuster, D.I.; Wilson, S.R. J. Am. Chem. Soc. 1997, in press; Baran, P.S.; Monaco, R.R.; Khan, A.U.; Schuster, D.I.; Wilson, S.R.; Boulas, P.; Echegoyen, L. Recent Advances in the Chemistry and Physics of Fullerenes and Related Materials 1997, in press.
14. Baran, P.S.; Monaco, R.R.; Khan, AU.; Schuster, D.I.; Wilson, S.R. J. Am. Chem. Soc. 1997, in press; Baran, P.S.; Monaco, R.R.; Khan, A.U.; Schuster, D.I.; Wilson, S.R.; Boulas, P.; Echegoyen, L. Recent Advances in the Chemistry and Physics of Fullerenes and Related Materials 1997, in press.
15. 60-methanocarboxylic acid (2): Isaacs, L.; Wehrsig, A.; Diederich, F. Helv. Chim. Acta. 1993, 76, 1231; Isaacs, L.; Diederich, F. ibid. 1993, 76, 2454; Wang, Y.; Cao, J.; Schuster, D.I.; Wilson, S.R. Tetrahedron Lett. 1995, 36, 6843.
16. 60-methanocarboxylic acid (2): Isaacs, L.; Wehrsig, A.; Diederich, F. Helv. Chim. Acta. 1993, 76, 1231; Isaacs, L.; Diederich, F. ibid. 1993, 76, 2454; Wang, Y.; Cao, J.; Schuster, D.I.; Wilson, S.R. Tetrahedron Lett. 1995, 36, 6843.
17. 60-methanocarboxylic acid (2): Isaacs, L.; Wehrsig, A.; Diederich, F. Helv. Chim. Acta. 1993, 76, 1231; Isaacs, L.; Diederich, F. ibid. 1993, 76, 2454; Wang, Y.; Cao, J.; Schuster, D.I.; Wilson, S.R. Tetrahedron Lett. 1995, 36, 6843.
18. Dhaon, M.K.; Olsen, R.K.; Ramasamy, K. J. Org. Chem. 1982, 47, 1962. EDC: N-(3-(dimethylamino)propyl)-N'-ethylcarbodiimide hydrochloride.
19. Matile, S.; Berova, N.; Nakanishi, K.; Novkova, S.; Philipova, I.; Blagoev, B. J. Am. Chem. Soc. 1995, 117, 7021; Anton, J.A.; Loach, P.A. J. Heterocycl. Chem. 1975, 12, 573; Stäubli, B.; Fretz, H.; Piantini, U.; Woggon, W.-D. Helv. Chim. Acta. 1987, 70, 1173; Kibbey, C.E.; Meyerhoff, M.E. Anal. Chem. 1993, 65, 2189.
20. Matile, S.; Berova, N.; Nakanishi, K.; Novkova, S.; Philipova, I.; Blagoev, B. J. Am. Chem. Soc. 1995, 117, 7021; Anton, J.A.; Loach, P.A. J. Heterocycl. Chem. 1975, 12, 573; Stäubli, B.; Fretz, H.; Piantini, U.; Woggon, W.-D. Helv. Chim. Acta. 1987, 70, 1173; Kibbey, C.E.; Meyerhoff, M.E. Anal. Chem. 1993, 65, 2189.
21. Matile, S.; Berova, N.; Nakanishi, K.; Novkova, S.; Philipova, I.; Blagoev, B. J. Am. Chem. Soc. 1995, 117, 7021; Anton, J.A.; Loach, P.A. J. Heterocycl. Chem. 1975, 12, 573; Stäubli, B.; Fretz, H.; Piantini, U.; Woggon, W.-D. Helv. Chim. Acta. 1987, 70, 1173; Kibbey, C.E.; Meyerhoff, M.E. Anal. Chem. 1993, 65, 2189.
22. Matile, S.; Berova, N.; Nakanishi, K.; Novkova, S.; Philipova, I.; Blagoev, B. J. Am. Chem. Soc. 1995, 117, 7021; Anton, J.A.; Loach, P.A. J. Heterocycl. Chem. 1975, 12, 573; Stäubli, B.; Fretz, H.; Piantini, U.; Woggon, W.-D. Helv. Chim. Acta. 1987, 70, 1173; Kibbey, C.E.; Meyerhoff, M.E. Anal. Chem. 1993, 65, 2189.
23. 2).
24. UV-VIS spectra were measured on a Perkin-Elmer Lambda LS-2 spectrophotometer. Data for hybrid 1: (acetone), 332 (36700), 428 (146800), 522 (12800), 552 (9000), 598 (5400), 656 (4100).
25. ex = 550 nm; c = 10 mmol; solvent = acetone; emission from 600-850 nm.
26. For a review on the design of similar systems see Cram, D.J.; Cram, J.M. Acc. Chem. Res. 1978, 11, 8; for similar systems, see Marquis, D.; Greiving, H.; Desvergne, J.-P.; Lahrahar, N.; Marsau, P.; Hopf, H.; Bouas-Laurent, H. Liebigs Ann. 1997, 97; Gokel, G.W. Crown Ethers and Cryptands (Ed.: J.F. Stoddart), The Royal Society of Chemistry, Cambridge, 1991 ; Tummler, B.; Maass, G.; Weber, E.; Wehner, W.; Vögtle, F. J. Am. Chem. Soc. 1977, 99, 4683.
27. For a review on the design of similar systems see Cram, D.J.; Cram, J.M. Acc. Chem. Res. 1978, 11, 8; for similar systems, see Marquis, D.; Greiving, H.; Desvergne, J.-P.; Lahrahar, N.; Marsau, P.; Hopf, H.; Bouas-Laurent, H. Liebigs Ann. 1997, 97; Gokel, G.W. Crown Ethers and Cryptands (Ed.: J.F. Stoddart), The Royal Society of Chemistry, Cambridge, 1991 ; Tummler, B.; Maass, G.; Weber, E.; Wehner, W.; Vögtle, F. J. Am. Chem. Soc. 1977, 99, 4683.
28. For a review on the design of similar systems see Cram, D.J.; Cram, J.M. Acc. Chem. Res. 1978, 11, 8; for similar systems, see Marquis, D.; Greiving, H.; Desvergne, J.-P.; Lahrahar, N.; Marsau, P.; Hopf, H.; Bouas-Laurent, H. Liebigs Ann. 1997, 97; Gokel, G.W. Crown Ethers and Cryptands (Ed.: J.F. Stoddart), The Royal Society of Chemistry, Cambridge, 1991 ; Tummler, B.; Maass, G.; Weber, E.; Wehner, W.; Vögtle, F. J. Am. Chem. Soc. 1977, 99, 4683.
29. For a review on the design of similar systems see Cram, D.J.; Cram, J.M. Acc. Chem. Res. 1978, 11, 8; for similar systems, see Marquis, D.; Greiving, H.; Desvergne, J.-P.; Lahrahar, N.; Marsau, P.; Hopf, H.; Bouas-Laurent, H. Liebigs Ann. 1997, 97; Gokel, G.W. Crown Ethers and Cryptands (Ed.: J.F. Stoddart), The Royal Society of Chemistry, Cambridge, 1991 ; Tummler, B.; Maass, G.; Weber, E.; Wehner, W.; Vögtle, F. J. Am. Chem. Soc. 1977, 99, 4683.
30. Khan, A.U. J. Am. Chem. Soc. 1981, 103, 6516; Khan, A.U. ACS Symp. Ser. 1987, 339, 58.
31. Khan, A.U. J. Am. Chem. Soc. 1981, 103, 6516; Khan, A.U. ACS Symp. Ser. 1987, 339, 58.
32. Ogilby, P.R.; Foote, C.S. J. Am. Chem. Soc. 1982, 104, 2069.
33. McLean, A.J.; McGarvey, D.J.; Truscott, T.G.; Lambert, C.R.; Land, E.J. J. Chem. Soc., Faraday Trans. 1990, 86, 3075; Schmidt, R., Afshari, E. J. Phys. Chem. 1990, 94, 4377.
34. McLean, A.J.; McGarvey, D.J.; Truscott, T.G.; Lambert, C.R.; Land, E.J. J. Chem. Soc., Faraday Trans. 1990, 86, 3075; Schmidt, R., Afshari, E. J. Phys. Chem. 1990, 94, 4377.
35. 2, 1 eq. TsCl, 1 eq. pyridine, 3 h, 54%;
36. 3, 15h, 55%;
37. 3N, 33%;
38. 2, 3 eq. DCC, 0.2 eq. DMAP, 1.1 eq. BtOH, PhBr:DMSO (5:1), 50°, 12h, 80%;
39. (e) 5% oxalic acid:MeOH, 5 min., 100%
40. 2:0.01N HCl/EtOH (100:1) 8h, 95%;
41. 2,12h, 70%.
42. This emission completely disappeared upon addition of β-carotene.