Rigid Molecular Tweezers: Preorganized Hosts for Electron Donor-Acceptor Complexation in Organic Solvents

Journal of the American Chemical Society

Volumn 111, Issue 4, 1989, Pages 1373-1381

  Zimmerman, Steven C ^a   VanZyl, Craig M ^a   Hamilton, Gregory S ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000619957     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00186a035     Document Type: Article

References (27)

1. Cf.: Foster, R. Organic Charge-Transfer Complexes; Academic: New York, 1969. Foster, R. J. Phys. Chem. 1980, 84, 2135–2141.
2. Cf.: Schanze, K. S.; Sauer, K. J. Am. Chem. Soc. 1988, 110, 1180–1186 and references therein.
3. Gale, E. F.; Cundliffe, E.; Reynolds, P. E.; Richmond, M. H.; Waring, M. J. The Molecular Basis of Antibiotic Action; Wiley: New York, 1981; Chapter 5.
4. DNA bis-intercalators: Wakelin, L. P. G. Med. Res. Rev. 1986, 6, 275–340.
5. Chen, C.-W.; Whitlock, H. W., Jr. J. Am. Chem. Soc. 1978, 100, 4921–4922.
6. Zimmerman, S. C.; VanZyl, C. M. J. Am. Chem. Soc. 1987, 109, 7894–7896.
7. Porphyrins have been linked in a syn cofacial orientation by shorter aromatic spacers: Fillers, J. P.; Ravichandran, K. G.; Abdalmuhdi, I.; Tulinksy, A.; Chang, C. K. J. Am. Chem. Soc. 1986, 108, 417–424 and references therein.
8. Recently, important studies have appeared in which the π-basicity of the guest molecule has been changed: Ferguson, S. B.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1986, 25, 1127–1129. Shepodd, T. J.; Petti, M. A.; Dougherty, D. A. J. Am. Chem. Soc. 1988, 110, 1983–1985. In a footnote to ref 8a the authors described a host with increased donor potential which shows altered guest affinities.
9. Mason, R. Proc. R. Soc. London, A 1960, 258, 302–318.
10. Cram, D. J. Angew. Chem., Int. Ed. Engl. 1986, 25, 1039-1055.
11. Tabushi, I.; Sasaki, H.; Kuroda, Y. J. Am. Chem. Soc. 1976, 98, 5727–5728. Odashima, K.; Itai, A.; Iitaka, Y.; Koga, K. J. Am. Chem. Soc. 1980, 102, 2504–2505. Jarvi, E. T.; Whitlock, H. W., Jr. J. Am. Chem. Soc. 1982, 104, 7196–7204. Diederich, F.; Dick, K. Angew. Chem., Int. Ed. Engl. 1983, 22, 715–716. Shepodd, T. J.; Petti, M. A.; Dougherty, D. A. J. Am. Chem. Soc. 1986, 108, 6085–6087. Wilcox, C. S.: Cowart, M. D. Tetrahedron Lett. 1986, 5563–5566.
12. Newman, M. S.; Seshardi, S. J. Org. Chem. 1962, 27, 76–78. Fieser, L. F.; Seligman, A. M. J. Am. Chem. Soc. 1938, 60, 170–177.
13. Lehmstedt, K.; Dostal, F. Chem. Ber. 1939, 72, 804–807.
14. Katritzky, A. R.; Thind, S. S. J. Chem. Soc., Perkin Trans. I 1980, 1895–1900. See also: Balaban, A. T.; Dinculescu, A.; Dorofeenko, G. N.; Fischer, G. W.; Koblik, A. V.; Mezheritskii, V. V.; Schroth, W. In Pyrylium Salts; Katritzky, A. R., Ed.; Advances in Heterocyclic Chemistry, Academic: New York, 1982; Chapter 2.
15. Balaban, A. T. C. R. Hebd. Seances Acad. Sci. 1963, 256, 4239–4242.
16. Adams, J. M.; Randas, S. Acta Crystallogr., Sect. B: Struct. Sci. 1979, 35, 679–683.
17. Carter, R. E.; Liljefors, T. Tetrahedron 1976, 32, 2915–2922.
18. Busing, W. R. J. Am. Chem. Soc. 1982, 104, 4829–4836.
19. Whitlock, B. J.; Jarvi, E. T.; Whitlock, H. W., Jr. J. Org. Chem. 1981, 46, 1832–1835. Adams, S. P.; Whitlock, H. W., Jr. J. Am. Chem. Soc. 1981, 46, 3474–3478. Adams, S. P.; Whitlock, H. W., Jr. J. Am. Chem. Soc. 1982, 104, 1602–1611.
20. Cf.: Whitlock, B. J.; Whitlock, H. W., Jr. J. Am. Chem. Soc. 1985, 107, 1325–1329.
21. Bergeron, R. J.; Roberts, W. P. Anal. Biochem. 1978, 90, 844–848. We thank a referee for pointing out our failure to meet the Hildebrand-Benesi boundary conditions.
22. Tazuke, S.; Nagahara, H.; Matsuyama, Y. Makromol. Chem. 1980, 181, 2199–2206.
23. Dorset, D. L.; Hyby, A.; Ammon, H. L. Acta Crystallogr., Sect. B: Struct. Sci. 1972, 3122–3127.
24. Emslie, P. H.; Foster, R.; Horman, J. W. M.; Twiselton, D. R. J. Chem. Soc. B 1969, 1161. Foster, R.; Payne, H. A. S. Recl. Trav. Chim. Pays-Bas 1971, 90, 630–632. See also: Foster, R.; Fyfe, C. A. J. Am. Chem. Soc. 1971, 90, 674–679.
25. Representative examples: Colquhoun, H. M.; Goodings, E. P.; Maud, J. N.; Stoddart. J. F.; Wolstenholme, J. B.; Williams, D. J. J. Chem. Soc., Perkin Trans. 2 1985, 607–624. Rebek, J., Jr. J. Am. Chem. Soc. 1985, 107, 6738–6739. Pirkle, W. H.; Pochapsky, T. C. J. Am. Chem. Soc. 1986, 108, 5627–5628.
26. Albert, A. The Acridines; Arnold: London, 1966; Chapters 2 and 3. The Acridines, 2nd ed.; Acheson, R. M., Ed.; The Chemistry of Heterocyclic Compounds, Wiley: New York, 1973; Chapter 3.
27. Still, W. C.; Kahn, M.; Mitra, A. J. J. Org. Chem. 1978, 43, 2923–2925.