Pyridinium N-phenolate betaine dyes and their application to the characterization of the polarity of solvents, XXII: Syntheses and UV/Vis spectroscopic properties of solvatochromic, halochromic, and chiro-solvatochromic pyridinium N-phenolate betaine dyes with four stereogenic centers

Liebigs Annales

Volumn , Issue 4, 1997, Pages 707-720

  Reichardt, Christian ^a   Blum, Andreas ^a   Harms, Klaus ^a   Schäfer, Gerhard ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Betaine dyes, chiral; Chirality; Crown compounds; Dyes; Halochromism; Solvatochromism

Indexed keywords

EID: 0042998927     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970411     Document Type: Article

References (73)

1. C. Reichardt, G. Schäfer, Liebigs Ann. 1995, 1579-1582.
2. A. Blum, Dissertation, University of Marburg, 1994.
3. Recent reviews on the various "-chromisms" of pyridinium N-phenolate betaine dyes: [3a] C. Reichardt, Chem. Soc. Rev. 1992, 21, 147-153;
4. [3b] C. Reichardt, S. Asharin-Fard, A. Blum, M. Eschner, A.-M. Mehranpour, P. Milart, T. Niem, G. Schäfer, M. Wilk, Pure Appl. Chem. 1993, 65, 2593-2601.
5. Recent review on solvatochromic dyes as solvent polarity indicators: C. Reichardt, Chem. Rev. 1994, 94, 2319-2358.
6. K. Dimroth, C. Reichardt, T. Siepmann, F. Bohlmann, Liebigs Ann. Chem. 1963, 661, 1-37.
7. For a recent pragmatic definition of the term "solvent polarity" see P. Müller, Glossary of Terms Used in Physical Organic Chemistry - IUPAC Recommendations 1994, Pure Appl. Chem. 1994, 66, 1077-1184.
8. [7a] C. Reichardt, E. Harbusch-Görnert, G. Schäfer, Liebigs Ann. Chem. 1988, 839-844;
9. [7b] C. Reichardt, G. Schäfer, P. Milart, Collect. Czech. Chem. Commun. 1990, 55, 97-118;
10. [7c] C. Reichardt, S. Asharin-Fard, G. Schäfer, Chem. Ber. 1993, 126, 143-147;
11. [7d] C. Reichardt, S. Asharin-Fard, G. Schäfer, Liebigs Ann. Chem. 1993, 23-34.
12. [8a] M. C. Rezende, D. Zanette, C. Zucco, Tetrahedron Lett. 1984, 25, 3423-3424;
13. [8b] M. C. Rezende, Tetrahedron 1988, 44, 3513-3522;
14. S. Zanotto, M. Scremin, V. G. Machado, M. C. Rezende, J. Phys. Org. Chem. 1993, 6, 637-641;
15. [8c] S. Zanotto, M. Scremin, V. G. Machado, M. C. Rezende, J. Chem. Soc., Faraday Trans. 1994, 90, 865-868.
16. [9a] R. J. Lavallee, M. B. Zimmt, J. Phys. Chem. 1994, 98, 4254-4260;
17. [9b] D. A. Binder, M. M. Kreevoy, J. Phys. Chem. 1994, 95, 10008-10016.
18. [10a] A. F. Sholl, I. O. Sutherland, J. Chem. Soc., Chem. Commun. 1992, 1716-1718;
19. [10b] M. Dolman, I. O. Sutherland, J. Chem. Soc., Chem. Commun. 1993, 1793-1795;
20. [10c] K. R. A. Samankumara Sandanayake, I. O. Sutherland, Tetrahedron Lett. 1993, 34, 3165-3168.
21. Reviews on chiro- solvatochromism: [11a] F. Vögtle, P. Knops, Angew. Chem. 1991, 103, 972-974;
22. Angew. Chem., Int. Ed. Engl. 1991, 30, 958-960;
23. [11b] M. V. Vinader, G. H. Posner, Chemtracts - Organic Chemistry, 1992, 5, 36-39.
24. C. Reichardt, M. Wilk, Liebigs Ann. Chem. 1990, 189-194.
25. M. S. Paley, J. M. Harris, J. Org. Chem. 1991, 56, 568-574.
26. We prefer the designations monochiral (one-handed), isochiral (equal-handed), and anisochiral (unequal-handed) in place of the ambigous terms homochiral, racemic, and scalemic, respectively, as recently recommended by J. W. Cornforth, Aust. J. Chem. 1993, 46, 157-170,
27. and Aldrichimica Acta 1994, 27(3), 71-77, footnote 21.
28. [15a] J. Fidler, P. M. Rodger, A. Rodger, J. Chem. Soc., Perkin Trans. 2 1993, 235-241;
29. [15b] J. Fidler, P. M. Rodger, A. Rodger, J. Am. Chem. Soc. 1994, 116, 7266-7273.
30. G. Hollmann, F. Vögtle, Chem. Ber. 1984, 117, 1355-1363.
31. [17a] T. Kaneda, K. Hirose, S. Misumi, J. Am. Chem. Soc. 1989, 111, 742-743;
32. [17b] S. Misumi, Pure Appl. Chem. 1990, 62, 493-498;
33. [17c] K. Naemura, S. Takeuchi, M. Asada, K. Ueno, K. Hirose, Y. Tobe, T. Kaneda, Y. Sakata, J. Chem. Soc., Perkin Trans. 1 1995, 1429-1435;
34. [17d] K. Naemura, M. Asada, K. Hirose, Y. Tobe, Tetrahedron: Asymmetry 1995, 6, 1873-1876;
35. [17e] K. Naemura, K. Ueno, S. Takeuchi, K. Hirose, Y. Tobe, T. Kaneda, Y. Sakata, J. Chem. Soc., Perkin Trans. 1 1996, 383-388.
36. K. Yamamoto, K. Isoue, Y. Sakata, T. Kaneda, J. Chem. Soc., Chem. Commun. 1992, 791-793.
37. [19a] J. S. Bradshaw, P. Huszthy, J. T. Redd, X. X. Zhang, T. Wang, J. K. Hathaway, J. Young, R. M. Izatt, Pure Appl. Chem. 1995, 67, 691-695;
38. [19b] R. M. Izatt, K. Pawlak, J. S. Bradshaw, R. L. Bruening, Chem. Rev. 1995, 95, 2529-2586.
39. [20a] T. Nishi, A. Ikeda, T. Matsuda, S. Shinkai, J. Chem. Soc., Chem. Commun. 1991, 339-341;
40. [20b] S. Shinkai, T. Nishi, T. Matsuda, Chem. Lett. 1991, 437-440;
41. [20c] T. D. James, H. Kawabata, R. Ludwig, K. Murata, S. Shinkai, Tetrahedron 1995, 51, 555-566.
42. Y. Kubo, S. Maeda, S. Tokita, M. Kubo, Nature, 1996, 382, 522-524.
43. [24].
44. [23a] E. N. Jacobsen, I. Markó, W. S. Mungall, G. Schröder, K. B. Sharpless, J. Am. Chem. Soc. 1988, 110, 1968-1970;
45. [23b] B. B. Lohray, T. H. Kalantar, B. M. Kim, C. Y. Park, T. Shibata, J. S. M. Wai, K. B. Sharpless, Tetrahedron Lett. 1989, 30, 2041-2044;
46. [23c] H.-L. Kwong, C. Sorato, Y. Ogino, H. Chen, K. B. Sharpless, Tetrahedron Lett. 1990, 31, 2999-3002;
47. [23d] Y. Ogino, H. Chen, H.-L. Kwong, K. B. Sharpless, Tetrahedron Lett. 1991, 32, 3965-3968;
48. [23e] K. B. Sharpless, W. Amberg, M. Beller, H. Chen, J. Hartung, Y. Kawanami, D. Lübben, E. Manoury, Y. Ogino, T. Shibata, T. Ukita, J. Org. Chem. 1991, 56, 4585-4588;
49. [23f] H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547 (particularly Table 3, Entry 7, on p. 2491).
50. K. v. Auwers, Th. Markovits, Ber. Dtsch. Chem. Ges. 1908, 41, 2332-2340 (particularly p. 2339).
51. [25a] F. Vögtle; p Neumann, Tetrahedron 1970, 26, 5299-5318;
52. [25b] C. M. Browne, G. Ferguson, M. A. McKervey, D. L. Mulholland, Th. O'Connor, M. Parvez, J. Am. Chem. Soc. 1985, 107, 2703-2712.
53. M. Sawada, Y. Okumura, M. Shizuma, Y. Takai, Y. Hidaka, H. Yamada, T. Tanaka, T. Kaneda, K. Hirose, S. Misumi, S. Takakashi, J. Am. Chem. Soc. 1993, 115, 7381-7388.
54. [27a] DuPont de Nemours and Co., Swiss Pat. 157662, 1930;
55. [Beilsteins Handbuch der organischen Chemie, 4th ed., vol. 11 (E 111), 1972, p. 225];
56. [27b] M. Ishidate, Y. Sakurai, S. Owari, Pharm. Bull. (Tokyo) 1957, 5, 203-207
57. [Chem. Abstr. 1958, 52, 6241i].
58. [28a] Q. I. Feutrill, R. N. Mirrington, Tetrahedron Lett. 1970, 16, 1327-1328;
59. [28b] G. I. Feutrill, R. N. Mirrington, Aust. J. Chem. 1972, 25, 1719-1729, 1731-1735;
60. [28c] K. Lal, S. Ghosh, R. G. Salomon, J. Org. Chem. 1987, 52, 1072-1078.
61. Further details of the crystal structure investigation are available from the Fachinformationszentrum Karlsruhe, D-76344 Egeenstein-Leopoldshafen (Germany), on quoting the depository number CSD-401986.
62. M. Quertani, P. Girard, H. B. Kagan, Tetrahedron Lett. 1982, 23, 4315-4318.
63. K. Dimroth, C. Reichardt, K. Vogel, Org. Synth. 1973, Collect. Vol. 5, 1135-1137.
64. [32a] A. R. Katritzky, R. H. Manzo, J. Chem. Soc., Perkin Trans. 2 1981, 571-575;
65. [32b] A. R. Katritzky, O. A. Schwarz, A. E. Abdel Rahman, D. E. Leahy, J. Heterocycl. Chem. 1984, 21, 1673-1677.
66. L. F. Tietze, Th. Eicher, Reaktionen und Synthesen im organischchemischen Praktikum und Forschungslaboratorium, 2nd ed., Thieme, Stuttgart, New York, 1991, p. 372-373.
67. [34a] W. Baker, K. M. Buggle, J. F. W. McOmie, D. A. M. Watkins, J. Chem. Soc. 1958, 3594-3603;
68. [34b] E. Weber, F. Vögtle, Chem. Ber. 1976, 109, 1803-1831.
69. [4,5].
70. [36a] G. N. Lewis, M. Randall, J. Am. Chem. Soc. 1921, 43, 1112-1154 (particularly p. 1141).
71. [36b] C. B. Monk, Chem. Br. 1993, 29, 1033-1034 (and references cited therein).
72. Aldrich-Chemie GmbH, D-89555 Steinheim, Germany; Catalogue 1994/95, p. 357, 861, and 862.
73. Fluka Chemie AG, CH-9471 Buchs, Switzerland; Catalogue 1995/96, p. 370 and 797.