Synthesis and characterization of non-aggregating octa-substituted azaphthalocyanines bearing bulky phenoxy substituents

Tetrahedron

Volumn 64, Issue 37, 2008, Pages 8871-8877

  Makhseed, Saad ^a   Samuel, Jacob ^a   Ibrahim, Fadi ^a  

^a KUWAIT UNIVERSITY   (Kuwait)

Author keywords

[No Author keywords available]

Indexed keywords

2,3,9,10,16,17,23,24 OCTA(2,6 DI ISO PROPYLPHENOXY)1,4,8,11,15,18,22,25 OCTAAZAPHTHALOCYANINATOCOBALT; 2,3,9,10,16,17,23,24 OCTA(2,6 DI ISO PROPYLPHENOXY)1,4,8,11,15,18,22,25 OCTAAZAPHTHALOCYANINATOZINC; 2,3,9,10,16,17,23,24 OCTA(2,6 DI ISO PROPYLPHENOXY)1,4,8,11,15,18,22,25 OCTAAZAPHTHALOCYANINE; 2,3,9,10,16,17,23,24 OCTA(2,6 DIPHENYLPHENOXY) 1,4,8,11,15,18,22,25 OCTAAZAPHTHALOCYANINATOCOBALT; 2,3,9,10,16,17,23,24 OCTA(2,6 DIPHENYLPHENOXY) 1,4,8,11,15,18,22,25 OCTAAZAPHTHALOCYANINATOZINC; 2,3,9,10,16,17,23,24 OCTA(2,6 DIPHENYLPHENOXY) 1,4,8,11,15,18,22,25 OCTAAZAPHTHALOCYANINE; 2,3,9,10,16,17,23,24,OCTA(2,6 DI ISOPROPYLPHENOXY) 1,4,8,11,15,18,22,25 OCTAAZAPHTHALOCYANINATONICKEL; 2,3,9,10,16,17,23,24,OCTA(2,6 DIPHENYLPHENOXY) 1,4,8,11,15,18,22,25 OCTAZAPHTHALOCYANINATONICKEL; 5,6 BIS(2,6 DIPHENYLPHENOXY)PYRAZINE 2,3 DICARBONITRILE; PHENOL DERIVATIVE; PHTHALOCYANINE DERIVATIVE;

ARTICLE; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; SOLUBILITY; SUBSTITUTION REACTION; ULTRAVIOLET SPECTROSCOPY;

EID: 48049105983     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.06.072     Document Type: Article

References (61)

1. Kudrevich S.V., and vanLier J.E. Coord. Chem. Rev. 156 (1996) 163-182
2. Freyer W. J. Prakt. Chem. 336 (1994) 690-692
3. Ghosh A., Gassman P.G.J., and AlmLof. J. Am. Chem. Soc. 116 (1994) 1932-1940
4. Kobayashi N., and Nevin W.A. Chem. Lett. (1998) 851-852
5. Musil Z., Zimcik P., Miletin M., Kopecky K., Petrik P., and Lenco J. J. Photochem. Photobiol., A 186 (2007) 316-322
6. Faust R. Eur. J. Org. Chem. (2001) 2797-2803
7. Faust R., and Weber C. J. Org. Chem. 64 (1999) 2571-2573
8. Linstead R.P., Noble E.G., and Wright J.M. J. Chem. Soc. (1937) 911-921
9. Kudrevich S.V., Gal'pern M.G., and van Lier J.E. Synthesis-Stuttgart (1994) 779-781
10. Zimcik P., Miletin M., Ponec J., Kostka M., and Fiedler Z. J. Photochem. Photobiol., A 155 (2003) 127-131
11. Mitzel F., FitzGerald S., Beeby A., and Faust R. Chem.-Eur. J. 9 (2003) 1233-1241
12. Mitzel F., FitzGerald S., Beeby A., and Faust R. Eur. J. Org. Chem. (2004) 1136-1142
13. Fox J.M., Katz T.J., Van Elshocht S., Verbiest T., Kauranen M., Persoons A., Thongpanchang T., Krauss T., and Brus L. J. Am. Chem. Soc. 121 (1999) 3453-3459
14. Wen T.C., Chen S.P., and Tsai C.Y. Synth. Met. 97 (1998) 105-112
15. Tsai C.Y., Chen S.P., and Wen T.C. Chem. Phys. 240 (1999) 191-196
16. Wen T.C., and Tsai C.Y. Chem. Phys. Lett. 311 (1999) 173-178
17. Hwang L.C., Tsai C.Y., Tiao C.J., and Wen T.C. Opt. Quantum Electron. 32 (2000) 641-656
18. Dini D., Hanack M., and Meneghetti M. J. Phys. Chem. B 109 (2005) 12691-12696
19. Vagin S., Barthel M., Dini D., and Hanack M. Inorg. Chem. 42 (2003) 2683-2694
20. Ohta K., Watanabe T., Fujimoto T., and Yamamoto I. J. Chem. Soc., Chem. Commun. (1989) 1611-1613
21. Ohta K., Watanabe T., Hasebe H., Morizumi Y., Fujimoto T., Yamamoto I., Lelievre D., and Simon J. Mol. Cryst. Liq. Cryst. 196 (1991) 13-26
22. Mohr B., Wegner G., and Ohta K. J. Chem. Soc., Chem. Commun. (1995) 995-996
23. Obirai J., and Nyokong T. Electrochim. Acta 50 (2005) 5427-5434
24. Maizish V.E., Korzheneveski A.B., and Klyuev V.N. Khim. Geterot. Soed. (1984) 1257-1259
25. Ashi T., Yoshikawa H.Y., Yashiro M., and Masuhara H. Appl. Surf. Sci. 197 and 198 (2002) 777-781
26. Lee B.H., and Jaung J.Y. Dyes Pigm. 65 (2005) 159-167
27. Musil Z., Zimcik P., Miletin M., Koopecky K., Petrik P., and Lencoo J. J. Photochem. Photobiol., A 186 (2007) 316-322
28. Jaung J.Y., Matsuoka M., and Fukunishi K. Dyes Pigm. 40 (1999) 73-81
29. Hassan B.M., Li H., and McKeoown N.B. J. Mater. Chem. 10 (2000) 39-45
30. Kostka M., Zimcik P., Miletin M., Klemera P., Kopecky K., and Musil Z. J. Photochem. Photobiol., A 178 (2006) 16-25
31. Dini D., Hanack M., Egelhaaf H.J., Carlos J., and Cornil J. J. Phys. Chem. B 109 (2005) 5425-5432
32. de la Torre G., Claessens C.G., and Torres T. Chem. Commun. (2007) 2000-2015
33. Jaung J.Y. Dyes Pigm. 75 (2007) 420-425
34. Fuchter M.J., Beall L.S., Baum S.M., Montalban A.G., Sakellariou E.G., Mani N.S., Miller T., Vesper B.J., White A.J.P., and Williams D.J. Tetrahedron 61 (2005) 6115-6130
35. Brewis M., Hassan B.M., Li H., Makhseed S., McKeown N.B., and Thompson N. J. Porphyrins Phthalocyanines 4 (2000) 460-464
36. Brewis M., Clarkson G.J., Holder A.M., and McKeown N.B. Chem. Commun. (1998) 969-970
37. McKeown N.B. Adv. Mater. 11 (1999) 67-69
38. McKeown N.B., Makhseed S., Msayib K.J., Ooi L.L., Helliwell M., and Warren J.E. Angew. Chem., Int. Ed. 44 (2005) 7546-7549
39. Suzuki T., Nagae Y., and Mitsuhashi K. J. Heterocycl. Chem. 23 (1986) 1419-1421
40. Wohrle D., Eskes M., Shigehara K., and Yamada A. Synthesis (1993) 194-196
41. Freyer W. J. Prakt. Chem. 336 (1994) 690-692
42. Mørkved E.H., Kjosen H., Ossletten H., and Erchak N. J. Porphyrins Phthalocyanines 3 (1999) 417-423
43. Wohrle D., Schnurpfeil G., and Knothe G. Dyes Pigm. 18 (1992) 91-102
44. Mørkved E.H., Osletten H., and Kjøsen H. Acta Chem. Scand. 53 (1999) 1117-1121
45. Makhseed S., Ibrahim F., Bezzu C.G., and McKeown N.B. Tetrahedron Lett. 48 (2007) 7358-7361
46. McKeown N.B. In: Kadish K., Smith K.M., and Guilard R. (Eds). The Porphyrin Handbook Vol. 15 (2003), Academic Press, Amsterdam 61-123
47. Sergeyev S., Pouzet E., Debever O., Levin J., Gierschner J., and Coornil J. J. Mater. Chem. 17 (2007) 1777-1784
48. Terekhov S.D., Nolan M.J.K., MacArthur R.C., and Leznoff C.C. J. Org. Chem. 61 (1996) 3034-3040
49. McKeown N.B. J. Mater. Chem. 10 (2000) 1979-1995
50. Macdonald I.J., and Dougherty T.J. J. Porphyrins Phthalocyanines 5 (2001) 105-129
51. Xu H.T., Xie W.W., Guo Y.C., Ci Y., Chen L.J., and Peng B.X. J. Chin. Chem. Soc. 54 (2007) 211-217
52. Law W.F., Lui K.M., and Ng D.K.P. J. Mater. Chem. 7 (1997) 2063-2067
53. Tai S., and Hayashi N. J. Chem. Soc., Perkin Trans. 2 (1991) 1275-1279
54. Choi M.T.M., Li P.P.S., and Ng D.K.P. Tetrahedron 56 (2000) 3881-3887
55. Flom S.R., Shirk J.S., Lindle J.R., Bartoli F.J., Kafafi Z.H., Pong R.G.S., and Snow A.W. Mater. Res. Soc. Symp. Proc. 247 (1992) 271-275
56. Stillman M.J., Nyokong T., Leznoff C.C., and Lever A.B.P. Phthalocyanines: Properties and Applications 1 (1989), VCH, New York, NY 133-289
57. Wu J., Fechtenkötter A., Gauss J., Watson M.D., Kastler M., Fechtenkötter C., Wagner M., and Müllen K. J. Am. Chem. Soc. 126 (2004) 11311-11321
58. Brewis M., Clarkson G.J., Humberstone P., Makhseed S., and McKeown N.B. Chem.-Eur. J. 4 (1998) 1633-1640
59. Makhseed S., McKeown N.B., Msayib K., and Bumajdad A. J. Mater. Chem. 15 (2005) 1-7
60. Vukusic P.S., Sambles J.R., and Wright J.D. J. Mater. Chem. 2 (1992) 1105-1106
61. Perrin D.D., and Armarego L.F. Purification of Laboratory Chemicals. 3rd ed. (1988), Pergamon, Oxford