Giant polycyclic aromatic hydrocarbons

Chemistry - A European Journal

Volumn 4, Issue 11, 1998, Pages 2099-2109

  Müller, Markus ^a   Kübel, Christian ^a   Müllen, Klaus ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

Author keywords

Arenes; C C coupling; Cyclizations; Dehydrogenations; Polycycles

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON;

CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; OXIDATION; REVIEW; SYNTHESIS; THEORY;

EID: 0031797589     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19981102)4:11<2099::AID-CHEM2099>3.0.CO;2-T     Document Type: Review

References (129)

1. Methoden Org. Chem. (Houben-Weyl), 4th ed., Vol. 5/2b: Arene und Arine (Ed.: C. Grundmann), Thieme, Stuttgart, New York, 1981.
2. E. Clar, Aromatische Kohlenwasserstoffe - Polycyclische Systeme, Springer, Berlin, Göttingen, Heidelberg, 1952.
3. M. Zander, Polycyclische Aromaten - Kohlenwasserstoffe und Fullerene, B. G. Teubner, Stuttgart, 1995.
4. R. G. Harvey, Polycyclic Aromatic Hydrocarbons, Wiley-VCH, New York, 1997.
5. E. Bäumler, Farben, Formeln, Forscher - Hoechst und die Geschichte der industriellen organischen Chemie in Deutschland, Serie R. Piper, München, Zürich, 1989.
6. R. Scholl, C. Seer, R. Weitzenböck, Chem. Ber. 1910, 43, 2202-2209.
7. R. Scholl, C. Seer, Liebigs Ann. Chem. 1912, 394, 111-123.
8. R. Scholl, H. Neumann. Chem. Ber. 1922, 55, 118-126.
9. R. Scholl, C. Seer, Chem. Ber. 1922, 55, 330-341.
10. E. Clar, D. G. Stewart, J. Am. Chem. Soc. 1953, 75, 2667-2672.
11. E. Clar, G. S. Fell, C. T. Ironside, A. Balsillie, Tetrahedron 1960, 10, 26-36.
12. E. Clar, C. T. Ironside, M. Zander, Tetrahedron 1966, 22, 3527-3533.
13. E. Clar, A. Mullen, Tetrahedron 1968, 24, 6719-6724.
14. E. Clar, A. Mullen, Ü. Sanigök, Tetrahedron 1969, 25, 5639-5648.
15. E. Clar, B. A. McAndrew, J. F. Stephen. Tetrahedron 1970, 26, 5465-5478.
16. E. Clar, B. A. McAndrew, Tetrahedron 1972, 28, 1137-1142.
17. E. Clar, B. A. McAndrew, Tetrahedron 1972, 25, 1237-1240.
18. E. Clar, C. C. Mackay, Tetrahedron 1972, 28, 5049-5054.
19. E. Clar, C. C. Mackay, Tetrahedron 1972, 25, 6041-6047.
20. E. Clar, M. M. Lovat, W. Simpson, Tetrahedron 1974, 30, 3293-3298.
21. E. Clar, W. Schmidt, Tetrahedron 1979, 35, 2673-2680.
22. M. Müller, H. Mauermann-Dïll, M. Wagner, V. Enkelmann, K. Müllen, Angew. Chem. 1995, 107, 1751-1754; Angew. Chem. Int. Ed. Engl. 1995, 34, 1583-1586.
23. M. Müller, H. Mauermann-Dïll, M. Wagner, V. Enkelmann, K. Müllen, Angew. Chem. 1995, 107, 1751-1754; Angew. Chem. Int. Ed. Engl. 1995, 34, 1583-1586.
24. A. Stabel, P. Herwig, K. Müllen, J. P. Rabe, Angew. Chem. 1995, 107, 1768-1770; Angrew. Chem. Int. Ed. Engl. 1995, 34, 1609-1611.
25. A. Stabel, P. Herwig, K. Müllen, J. P. Rabe, Angew. Chem. 1995, 107, 1768-1770; Angrew. Chem. Int. Ed. Engl. 1995, 34, 1609-1611.
26. P. Herwig, C. W. Kayser, K. Müllen, H. W. Spiess, Adv. Mater. 1996, 8, 510-513.
27. M. Müller, J. Petersen, R. Strohmaier, C. Günther, N. Karl, K. Müllen, Angew. Chem. 1996, 108, 947-950; Angew. Chem. Int. Ed. Engl. 1996, 35, 886-888.
28. M. Müller, J. Petersen, R. Strohmaier, C. Günther, N. Karl, K. Müllen, Angew. Chem. 1996, 108, 947-950; Angew. Chem. Int. Ed. Engl. 1996, 35, 886-888.
29. F. Morgenroth, E. Reuther, K. Müllen, Angew. Chem. 1997, 109, 647-649; Angew. Chem. Int. Ed. Engl. 1997, 56, 631-634.
30. F. Morgenroth, E. Reuther, K. Müllen, Angew. Chem. 1997, 109, 647-649; Angew. Chem. Int. Ed. Engl. 1997, 56, 631-634.
31. V. S. Iyer, M. Wehmeier, J. D. Brand, M. A. Keegstra, K. Müllen, Angew. Chem. 1997, 109, 1676-1679; Angew. Chem. Int. Ed. Engl. 1997, 36, 1604-1607.
32. V. S. Iyer, M. Wehmeier, J. D. Brand, M. A. Keegstra, K. Müllen, Angew. Chem. 1997, 109, 1676-1679; Angew. Chem. Int. Ed. Engl. 1997, 36, 1604-1607.
33. M. Müller, V. S. Iyer, C. Kübel, V. Enkelmann, K. Müllen, Angew. Chem. 1997, 109, 1679-1682; Angew. Chem. Int. Ed. Engl. 1997, 36, 1607-1610.
34. M. Müller, V. S. Iyer, C. Kübel, V. Enkelmann, K. Müllen, Angew. Chem. 1997, 109, 1679-1682; Angew. Chem. Int. Ed. Engl. 1997, 36, 1607-1610.
35. F. Morgenroth, K. Müllen, Tetrahedron 1997, 55, 15349-15366.
36. F. Morgenroth, C. Kübel, K. Müllen, J. Mater. Chem. 1997, 7, 1207-1211.
37. A. M. van de Craats, J. M. Warman, K. Müllen, Y. Geerts, J. D. Brand, Adv. Mater. 1998, 10, 36-38.
38. M. Müller, C. Kübel, F. Morgenroth, V. S. Iyer, K. Müllen, Carbon 1998, 36, 827-831.
39. F. Morgenroth, C Kübel, M. Müller, U.-M. Wiesler, A. J. Berresheim, M. Wagner, K. Müllen, Carbon 1998, 36, 833-837.
40. A. J. Berresheim, F. Morgenroth, U.-M. Wiesler, K. Müllen, Polym. Prep. 1998, 39 (1st series), 721-722.
41. C. J. Cyvin, J. Brunvoll, B. N. Cyvin, Lecture Notes in Chemistry, Vol. 54: Theory of Coronoid Hydrocarbons, Springer, Berlin, Heidelberg, New York, 1991.
42. W. C. Herndon, J. Am. Chem. Soc. 1990, 112, 4546-4547.
43. D. Boucher, O. Mekenyan, E. O. Polansky, Z. Naturforsch. A: Phys. Sci. 1981, 36a, 647-650.
44. S. E. Stein, R. L. Brown, in Molecular Structure and Energetics, Vol. 2 (Eds.: J. F. Liebman, A. Greenberg), VCH, Weinheim, New York, 1987, p. 37-66.
45. S. E. Stein, R. L. Brown, J. Am. Chem. Soc. 1987, 109, 3721-3729.
46. J. R. Dias, Handbook of Polycyclic Hydrocarbons, A: Benzenoid Hydrocarbons, Elsevier, Amsterdam. 1987.
47. J. R. Dias, J. Chem. Inf. Comput. Sci. 1991, 31, 89-96.
48. J. R. Dias, J. Chem. Inf. Comput. Sci. 1993, 33, 117-127.
49. J. R. Dias, Z. Naturforsch. A: Phys. Sci. 1989, 44a, 785-791.
50. J. R. Dias, Thermochim. Acta 1987, 122, 313-337.
51. J. L. Bredas, R. H. Baughman, J. Chem. Phys. 1985, 83, 1316-1322.
52. M. Zander, Top. Curr. Chem., Vol. 153: Advances in the Theory of Benzenoid Hydrocarbons, Springer, Berlin, Heidelberg, 1990, pp. 101-122.
53. H. Hosoya, in ref. [46]. pp. 255-272.
54. J. W. Cook, C. L. Hewett, I. Hieger, J. Chem. Soc. 1933, 395-405.
55. L. J. Allamandola, in ref. [46], pp. 1-25.
56. D. J. Cook, S. Schlemmer, N. Balucani, D. R. Wagner, B. Steiner, R. J. Saykally, Nature 1996, 380, 227-229.
57. L. J. Allamandola, A. G. G. M. Tielens, J. R. Barker, Astrophys. J. Suppl. Ser. 1989, 71, 733-775.
58. I. Gutman, C. J. Cyvin, Introduction to the Theory of Benzenoid Hydrocarbons, Springer, Berlin, Heidelberg, 1989.
59. E. Clar, The Aromatic Sextet, Wiley, London, 1972.
60. J. W. Armit, R. Robinson J. Chem. Soc. 1925, 1604-1618.
61. B. A. Hess, Jr., L. S. Schaad, J. Am. Chem. Soc. 1971, 93, 305-310.
62. D. Biermann, W. Schmidt, J. Am. Chem. Soc. 1980, 102, 3163-3173.
63. J. C. Fetzer, W. R. Biggs, Polycycl. Arom. Compd. 1994, 4, 3-17.
64. J. C. Fetzer, Org. Prep. Proced. Int. 1989, 27, 47-65.
65. M. Zander, DGMK-Compendium, 24. Haupttagung der Deutschen Gesellschaft für Mineralölwissenschaft und Kohlechemie e.V., Vol. 2, 1974, 721-731.
66. N. Miyaura, T. Yanagi, A. Suzuki, Synth. Commun. 1981, 77, 513-519.
67. A. R. Martin, Y. Yang, Acta Chem. Scand. 1993, 47, 221-230.
68. N. Miyaura, T. Ishiyama, H. Sasaki, M. Ishikawa, M. Satoh, A. Suzuki, J. Am. Chem. Soc. 1989, 111, 314-321.
69. A. Halleux, R. H. Martin, G. S. D. King, Helv. Chim. Acta 1958, 41, 1177-1183.
70. J. A. Hyatt, Org. Prep. Proced. Int. 1991, 23, 460-463.
71. K. P. C. Vollhardt, Acc. Chem. Res. 1977, 10, 1-8.
72. R. B. King, I. Haiduc, A. Efraty, J. Organomet. Chem. 1973, 47, 145-151.
73. R. Diercks, K. P. C. Vollhardt, J. Am. Chem. Soc. 1986, 108, 3150-3153.
74. K. P. C. Vollhardt, Angew. Chem. 1984, 96, 525-541; Angew. Chem. Int. Ed. Engl. 1984, 23, 539-555.
75. K. P. C. Vollhardt, Angew. Chem. 1984, 96, 525-541; Angew. Chem. Int. Ed. Engl. 1984, 23, 539-555.
76. H. A. Dieck, F. R. Heck, J. Organomet. Chem. 1975, 93, 259-263.
77. L. Cassar, J. Organomet. Chem. 1975, 93, 253-257.
78. S. Takahashi, Y. Koroyama, K. Sonogashira, N. Hagihara, Synthesis 1980, 627-630.
79. W. Dilthey, W. Schommer, W. Höschen, H. Dierichs, Chem. Ber. 1935, 68, 1159-1162.
80. W. Dilthey, I. Thewalt, O. Trösken, Chem. Ber. 1934, 67, 1959-1964.
81. W. Dilthey, G. Hurtig, Chem. Ber. 1934, 67, 2004-2007.
82. W. Dilthey, G. Hurtig, Chem. Ber. 1934, 67, 495-496.
83. W. Dilthey, W. Schommer, O. Trösken, Chem. Ber. 1933, 66, 1627-1628.
84. L. F. Fieser, Organic Experiments, D. C. Heath, Boston. 1964, pp. 307-308.
85. W. Ried, V. B. Saxena, Angew. Chem. 1968, 80, 366; Angew. Chem. Int. Ed. Engl 1968, 7, 378-379.
86. W. Ried, V. B. Saxena, Angew. Chem. 1968, 80, 366; Angew. Chem. Int. Ed. Engl 1968, 7, 378-379.
87. W. Ried, V. B. Saxena, Liebigs Ann. Chem. 1970, 739, 159-165.
88. W. Ried, D. Freitig, Angew. Chem. 1968, 80, 932-942; Angew. Chem. Int. Ed. Engl. 1968, 7, 835-845.
89. W. Ried, D. Freitig, Angew. Chem. 1968, 80, 932-942; Angew. Chem. Int. Ed. Engl. 1968, 7, 835-845.
90. W. Ried, K. H. Bönninghausen, Chem. Ber. 1960, 93, 1769-1773.
91. M. A. Ogliaruso, L. A. Schadoff, E. I. Becker, J. Org. Chem. 1963, 28, 2725-2728.
92. M. A. Ogliaruso, E. I. Becker, J. Org. Chem. 1965, 30, 3354-3360.
93. J. A. Harvey, M. A. Ogliaruso, J. Chem. Engin. Data 1977, 22, 110-113.
94. A. J. Liepa, R. E. Summons, J. Chem. Soc. Chem. Commun. 1977, 826-827.
95. T. Biftu, B. G. Hazra, R. Stevenson, J. Chem. Soc. Perkin Trans. I 1979, 2267-2281.
96. J. S. Bradshaw, L. Golic, M. Tišler, Monatsh. Chemie 1988, 119, 327-332.
97. A. G. Brown, P. D. Edwards, Tetrahedron Lett. 1990, 31, 6581-6584.
98. S. M. Kupchan, O. P. Dhingra, C.-K. Kim, J. Org. Chem. 1978, 43, 4076-4081.
99. E. C. Taylor, J. G. Andrada, G. J. H. Rall, A. McKillop, J. Am. Chem. Soc. 1980, 102, 6513-6519.
100. M. A. Schwartz, P. T. K. Pham, J. Org. Chem. 1988, 53, 2318-2322.
101. M. A. Schwartz, M. F. Zoda, J. Org. Chem. 1981, 46, 4623-4625.
102. P. Magnus, J. Schultz, T. Gallagher, J. Am. Chem. Soc. 1985, 107, 4984-4988.
103. N. Boden, R. J. Bushby, A. N. Cammidge, G. Headdock, Synthesis 1995, 31-32.
104. R. J. Bushby, C. Hardy, J Chem. Soc. Perkin Trans. I 1986, 721-723.
105. T. Sato, Y. Goto, K. Hata, Bull. Chem. Soc. Jpn. 1967, 40, 1994-1995.
106. T. Sato, S. Shimada, K. Hata, Bull. Chem. Soc. Jpn. 1971, 44, 2484-2490.
107. L. Liu, B. Yang, T. J. Katz, M. K. Poindexter, J. Org. Chem. 1991, 56, 3769-3775.
108. W. Jaworek, F. Vögtle, Chem. Ber. 1991, 124, 347-352.
109. K.-H. Koch, K. Müllen, Chem. Ber. 1991, 124, 2091-2100.
110. P. G. Copeland, R. E. Dean, D. McNeil, J. Chem. Soc. 1960, 1689-1691.
111. C. F. H. Allen, F. P. Pingert, J. Am. Chem. Soc. 1942, 64, 1365-1371.
112. P. Kovacic, C. Wu, J. Polymer Sci. 1960, 47, 45-54.
113. P. Kovacic, A. Kyriakis, Tetrahedron Lett. 1962, 467-469.
114. P. Kovacic, A. Kyriakis, J. Am. Chem. Soc. 1963, 85, 454-458.
115. P. Kovacic, R. M. Lange, J. Org. Chem. 1963, 25, 968-972.
116. P. Kovacic, F. W. Koch, J. Org. Chem. 1963, 28, 1864-1867.
117. P. Kovacic, J. Oziomek, J. Org. Chem. 1964, 29, 100-104.
118. P. Kovacic, L. C. Hsu, J. Polymer Sci. 1966, 4, 5-28.
119. P Kovacic, R. J. Hopper, J. Polymer Sci. 1966, 4, 1445.
120. J. G. Speight, P. Kovacic, F. W. Koch, Macromol Rev. 1971, 5, 295-386.
121. P. Kovacic, M. B. Jones, Chem. Rev. 1987, 87, 357-379.
122. S. Ito, M. Wehmeier, J. D. Brand, C. Kübel, R. Epsch, J. P. Rabe, K. Müllen, J. Am. Chem. Soc. 1998, submitted.
123. C. Günther, N. Karl, R. Strohmaier, W. Eisenmenger, M. Müller, K. Müllen, N. Sato, Surf Sci. 1998, submitted.
124. D. Adam, P. Schuhmacher, J. Simmerer, L. Häussling, K. Siemensmeyer, K. H. Etzbach, H. Ringsdorf, D. Haarer, Nature 1994, 371, 141-143.
125. G. R. Desiraju, A. Gavezzotti, J. Chem. Soc. Chem. Commun. 1989, 621-623.
126. G. R. Desiraju, A. Gavezzotti, Acta Crystallogr. Sect. B 1988, 44, 427-434.
127. G. R. Desiraju, A. Gavezzotti, Acta Crystallogr. Sect. B 1989, 45, 473-482.
128. P. Herwig, V. Enkelmann, K. Müllen, unpublished results.
129. R. Strohmaier, STM-Bildkontrast und Monolagenkristallographie planarer Aromaten, Stuttgart University, 1997.