Visible Aromatic Electronic Effects Using a Series of Substituted Copper Phthalocyanines

Journal of Chemical Education

Volumn 77, Issue 11, 2000, Pages 1482-1483

  MacFarland, Darren K ^a   Lieb, Solomon ^a   Oswald, Jessica ^a  

^a ILLINOIS COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0345853620     PISSN: 00219584     EISSN: None     Source Type: Journal    
DOI: 10.1021/ed077p1482     Document Type: Article

References (19)

1. For a broad review, see Phthalocyanines: Properties and Applications; Leznoff, C. C.; Lever, A. B. P., Eds.; VCH: New York, 1989; 4 vols.
2. Copper phthalocyanine is sold as Pigment Blue; it was discovered in 1907 - see: von Braun, A.; Tcherniak, J. Chem. Ber. 1907, 40, 2709.
3. Hanack, M.; Deger, S.; Lange, A. Coord. Chem. Rev. 1988, 83, 115. Ruf, M.; Lawrence, A. M.; Noll, B. C., Pierpont, C. G. Inorg. Chem. 1998, 37, 1992-1997 and references cited therein. Ali, H.; van Lier, J. E. Chem. Rev. 1999, 99, 2379-2450.
4. Hanack, M.; Deger, S.; Lange, A. Coord. Chem. Rev. 1988, 83, 115. Ruf, M.; Lawrence, A. M.; Noll, B. C., Pierpont, C. G. Inorg. Chem. 1998, 37, 1992-1997 and references cited therein. Ali, H.; van Lier, J. E. Chem. Rev. 1999, 99, 2379-2450.
5. Hanack, M.; Deger, S.; Lange, A. Coord. Chem. Rev. 1988, 83, 115. Ruf, M.; Lawrence, A. M.; Noll, B. C., Pierpont, C. G. Inorg. Chem. 1998, 37, 1992-1997 and references cited therein. Ali, H.; van Lier, J. E. Chem. Rev. 1999, 99, 2379-2450.
6. Metz, J.; Schneider, O.; Hanack, M. Inorg. Chem. 1984, 23, 1065-1071.
7. The only J. Chem. Educ. references to phthalocyanines are: Joesten, M. D.; Higgins, M. M. J. Chem. Educ. 1986, 63, 1097-1098. Moser, F. H.; Thomas, A. L. J. Chem. Educ. 1964, 41, 245-249.
8. The only J. Chem. Educ. references to phthalocyanines are: Joesten, M. D.; Higgins, M. M. J. Chem. Educ. 1986, 63, 1097-1098. Moser, F. H.; Thomas, A. L. J. Chem. Educ. 1964, 41, 245-249.
9. Pawlowski, G.; Hanack, M. Synthesis 1980, 287-289. Hanack, M.; Heckmann, H. Eur. J. Inorg. Chem. 1998, 367-373. Brewis, M.; Clarkson, G. J.; Humberstone, P.; Makhseed, S.; McKeown, N. B. Chem. Eur. J. 1998, 4, 1633-1640.
10. Pawlowski, G.; Hanack, M. Synthesis 1980, 287-289. Hanack, M.; Heckmann, H. Eur. J. Inorg. Chem. 1998, 367-373. Brewis, M.; Clarkson, G. J.; Humberstone, P.; Makhseed, S.; McKeown, N. B. Chem. Eur. J. 1998, 4, 1633-1640.
11. Pawlowski, G.; Hanack, M. Synthesis 1980, 287-289. Hanack, M.; Heckmann, H. Eur. J. Inorg. Chem. 1998, 367-373. Brewis, M.; Clarkson, G. J.; Humberstone, P.; Makhseed, S.; McKeown, N. B. Chem. Eur. J. 1998, 4, 1633-1640.
12. A discussion of the template effect can be found in: Shriver, D.; Atkins, P. W. H. Inorganic Chemistry, 3rd ed.; Freeman: New York, 1999; pp 222-223. Sheeran, D. J.; Mertes, K. B. J. Am. Chem. Soc. 1990, 112, 1055-1061, and references contained therein.
13. A discussion of the template effect can be found in: Shriver, D.; Atkins, P. W. H. Inorganic Chemistry, 3rd ed.; Freeman: New York, 1999; pp 222-223. Sheeran, D. J.; Mertes, K. B. J. Am. Chem. Soc. 1990, 112, 1055-1061, and references contained therein.
14. 2h. For further discussion, see: (a) Hanack, M.; Schmid, G.; Sommerauer, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1422-1424. (b) Rager, C.; Schmid, G.; Hanack, M. Chem. Eur. J. 1999, 5, 280-288.
15. 2h. For further discussion, see: (a) Hanack, M.; Schmid, G.; Sommerauer, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1422- 1424. (b) Rager, C.; Schmid, G.; Hanack, M. Chem. Eur. J. 1999, 5, 280-288.
16. Metz, J.; Schneider, O.; Hanack, M. Inorg. Chem. 1984, 23, 1065-1071.
17. Redemann, C. T.; Redemann, C. E. In Organic Syntheses; Wiley: New York, 1955; Collect. Vol. III, p 69. Williamson, K. L. Macroscale and Microscale Organic Experiments, 3rd ed.; Houghton Mifflin: Boston, 1999; p 564.
18. Redemann, C. T.; Redemann, C. E. In Organic Syntheses; Wiley: New York, 1955; Collect. Vol. III, p 69. Williamson, K. L. Macroscale and Microscale Organic Experiments, 3rd ed.; Houghton Mifflin: Boston, 1999; p 564.
19. For example, our school has used a reaction of dinitrochlorobenzene with NaOMe, with product identification by melting point. An alternative is a discussion of acidities of nitrophenols, such as found in Wade, L. G. Organic Chemistry, 4th ed.; Prentice-Hall: Englewood Cliffs, NJ, 1999; p 429.