Bishexa-peri-hexabenzocoronenyl: A 'superbiphenyl'

Journal of the American Chemical Society

Volumn 122, Issue 32, 2000, Pages 7698-7706

  Ito, Shunji ^a   Herwig, Peter Tobias ^a   Böhme, Thilo ^b   Rabe, Jürgen P ^b   Rettig, Wolfgang ^b   Müllen, Klaus ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

^b HUMBOLDT UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; ORGANIC SOLVENT; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; CHEMICAL STRUCTURE; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SCANNING TUNNELING MICROSCOPY; SOLUBILITY; SYNTHESIS;

EID: 0034675019     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000850e     Document Type: Article

References (44)

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8. For further examples of extended polycyclic aromatic hydrocarbons, see: (a) Clar, E. Aromatische Kohlenwasserstoffe-Polycyclische Systeme; Springer, Berlin, 1952. (b) Clar, E. The Aromatic Sextet; Wiley: London, 1972. (c) Dias, J. R. Handbook of Polycyclic Hydrocarbons-Part a: Benzenoid Hydrocarbons; Elsevier: Amsterdam, 1987. (d) Fetzer, J. C. Polycycl. Aromat. Comput. 1996, 11 (1-4), 317; (e) Diederich, F.; Rubin, Y. Angew. Chem. 1992, 104, 1123; Angew. Chem., Int. Ed. Engl. 1992, 31, 1101. (f) Hudgins, D. M.; Allamandola, L. J. J. Phys. Chem. 1995, 99, 3033. (g) Scott, L. T.; Cheng, P.-C.; Hashemi, M. M.; Bratcher, M. S.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1997, 119, 10963. (h) Faust, R. Angew. Chem. 1995, 107, 1559; Angew. Chem., Int. Ed. Engl. 1995, 34, 1429. (i) Müller, M.; Petersen, J.; Strohmaier, R.; Günther, C.; Karl, N.; Müllen, K. Angew. Chem. 1996, 108, 947; Angew. Chem., Int. Ed. Engl. 1996, 35, 886. (j) Tong, L.; Lau, H.; Ho, D. M.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1998, 120, 6000. (k) Debad, J. D.; Bard, A. J. J. Am. Chem. Soc. 1998, 120, 2476.
9. For further examples of extended polycyclic aromatic hydrocarbons, see: (a) Clar, E. Aromatische Kohlenwasserstoffe-Polycyclische Systeme; Springer, Berlin, 1952. (b) Clar, E. The Aromatic Sextet; Wiley: London, 1972. (c) Dias, J. R. Handbook of Polycyclic Hydrocarbons-Part a: Benzenoid Hydrocarbons; Elsevier: Amsterdam, 1987. (d) Fetzer, J. C. Polycycl. Aromat. Comput. 1996, 11 (1-4), 317; (e) Diederich, F.; Rubin, Y. Angew. Chem. 1992, 104, 1123; Angew. Chem., Int. Ed. Engl. 1992, 31, 1101. (f) Hudgins, D. M.; Allamandola, L. J. J. Phys. Chem. 1995, 99, 3033. (g) Scott, L. T.; Cheng, P.-C.; Hashemi, M. M.; Bratcher, M. S.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1997, 119, 10963. (h) Faust, R. Angew. Chem. 1995, 107, 1559; Angew. Chem., Int. Ed. Engl. 1995, 34, 1429. (i) Müller, M.; Petersen, J.; Strohmaier, R.; Günther, C.; Karl, N.; Müllen, K. Angew. Chem. 1996, 108, 947; Angew. Chem., Int. Ed. Engl. 1996, 35, 886. (j) Tong, L.; Lau, H.; Ho, D. M.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1998, 120, 6000. (k) Debad, J. D.; Bard, A. J. J. Am. Chem. Soc. 1998, 120, 2476.
10. For further examples of extended polycyclic aromatic hydrocarbons, see: (a) Clar, E. Aromatische Kohlenwasserstoffe-Polycyclische Systeme; Springer, Berlin, 1952. (b) Clar, E. The Aromatic Sextet; Wiley: London, 1972. (c) Dias, J. R. Handbook of Polycyclic Hydrocarbons-Part a: Benzenoid Hydrocarbons; Elsevier: Amsterdam, 1987. (d) Fetzer, J. C. Polycycl. Aromat. Comput. 1996, 11 (1-4), 317; (e) Diederich, F.; Rubin, Y. Angew. Chem. 1992, 104, 1123; Angew. Chem., Int. Ed. Engl. 1992, 31, 1101. (f) Hudgins, D. M.; Allamandola, L. J. J. Phys. Chem. 1995, 99, 3033. (g) Scott, L. T.; Cheng, P.-C.; Hashemi, M. M.; Bratcher, M. S.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1997, 119, 10963. (h) Faust, R. Angew. Chem. 1995, 107, 1559; Angew. Chem., Int. Ed. Engl. 1995, 34, 1429. (i) Müller, M.; Petersen, J.; Strohmaier, R.; Günther, C.; Karl, N.; Müllen, K. Angew. Chem. 1996, 108, 947; Angew. Chem., Int. Ed. Engl. 1996, 35, 886. (j) Tong, L.; Lau, H.; Ho, D. M.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1998, 120, 6000. (k) Debad, J. D.; Bard, A. J. J. Am. Chem. Soc. 1998, 120, 2476.
11. For further examples of extended polycyclic aromatic hydrocarbons, see: (a) Clar, E. Aromatische Kohlenwasserstoffe-Polycyclische Systeme; Springer, Berlin, 1952. (b) Clar, E. The Aromatic Sextet; Wiley: London, 1972. (c) Dias, J. R. Handbook of Polycyclic Hydrocarbons-Part a: Benzenoid Hydrocarbons; Elsevier: Amsterdam, 1987. (d) Fetzer, J. C. Polycycl. Aromat. Comput. 1996, 11 (1-4), 317; (e) Diederich, F.; Rubin, Y. Angew. Chem. 1992, 104, 1123; Angew. Chem., Int. Ed. Engl. 1992, 31, 1101. (f) Hudgins, D. M.; Allamandola, L. J. J. Phys. Chem. 1995, 99, 3033. (g) Scott, L. T.; Cheng, P.-C.; Hashemi, M. M.; Bratcher, M. S.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1997, 119, 10963. (h) Faust, R. Angew. Chem. 1995, 107, 1559; Angew. Chem., Int. Ed. Engl. 1995, 34, 1429. (i) Müller, M.; Petersen, J.; Strohmaier, R.; Günther, C.; Karl, N.; Müllen, K. Angew. Chem. 1996, 108, 947; Angew. Chem., Int. Ed. Engl. 1996, 35, 886. (j) Tong, L.; Lau, H.; Ho, D. M.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1998, 120, 6000. (k) Debad, J. D.; Bard, A. J. J. Am. Chem. Soc. 1998, 120, 2476.
12. For further examples of extended polycyclic aromatic hydrocarbons, see: (a) Clar, E. Aromatische Kohlenwasserstoffe-Polycyclische Systeme; Springer, Berlin, 1952. (b) Clar, E. The Aromatic Sextet; Wiley: London, 1972. (c) Dias, J. R. Handbook of Polycyclic Hydrocarbons-Part a: Benzenoid Hydrocarbons; Elsevier: Amsterdam, 1987. (d) Fetzer, J. C. Polycycl. Aromat. Comput. 1996, 11 (1-4), 317; (e) Diederich, F.; Rubin, Y. Angew. Chem. 1992, 104, 1123; Angew. Chem., Int. Ed. Engl. 1992, 31, 1101. (f) Hudgins, D. M.; Allamandola, L. J. J. Phys. Chem. 1995, 99, 3033. (g) Scott, L. T.; Cheng, P.-C.; Hashemi, M. M.; Bratcher, M. S.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1997, 119, 10963. (h) Faust, R. Angew. Chem. 1995, 107, 1559; Angew. Chem., Int. Ed. Engl. 1995, 34, 1429. (i) Müller, M.; Petersen, J.; Strohmaier, R.; Günther, C.; Karl, N.; Müllen, K. Angew. Chem. 1996, 108, 947; Angew. Chem., Int. Ed. Engl. 1996, 35, 886. (j) Tong, L.; Lau, H.; Ho, D. M.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1998, 120, 6000. (k) Debad, J. D.; Bard, A. J. J. Am. Chem. Soc. 1998, 120, 2476.
13. For further examples of extended polycyclic aromatic hydrocarbons, see: (a) Clar, E. Aromatische Kohlenwasserstoffe-Polycyclische Systeme; Springer, Berlin, 1952. (b) Clar, E. The Aromatic Sextet; Wiley: London, 1972. (c) Dias, J. R. Handbook of Polycyclic Hydrocarbons-Part a: Benzenoid Hydrocarbons; Elsevier: Amsterdam, 1987. (d) Fetzer, J. C. Polycycl. Aromat. Comput. 1996, 11 (1-4), 317; (e) Diederich, F.; Rubin, Y. Angew. Chem. 1992, 104, 1123; Angew. Chem., Int. Ed. Engl. 1992, 31, 1101. (f) Hudgins, D. M.; Allamandola, L. J. J. Phys. Chem. 1995, 99, 3033. (g) Scott, L. T.; Cheng, P.-C.; Hashemi, M. M.; Bratcher, M. S.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1997, 119, 10963. (h) Faust, R. Angew. Chem. 1995, 107, 1559; Angew. Chem., Int. Ed. Engl. 1995, 34, 1429. (i) Müller, M.; Petersen, J.; Strohmaier, R.; Günther, C.; Karl, N.; Müllen, K. Angew. Chem. 1996, 108, 947; Angew. Chem., Int. Ed. Engl. 1996, 35, 886. (j) Tong, L.; Lau, H.; Ho, D. M.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1998, 120, 6000. (k) Debad, J. D.; Bard, A. J. J. Am. Chem. Soc. 1998, 120, 2476.
14. For further examples of extended polycyclic aromatic hydrocarbons, see: (a) Clar, E. Aromatische Kohlenwasserstoffe-Polycyclische Systeme; Springer, Berlin, 1952. (b) Clar, E. The Aromatic Sextet; Wiley: London, 1972. (c) Dias, J. R. Handbook of Polycyclic Hydrocarbons-Part a: Benzenoid Hydrocarbons; Elsevier: Amsterdam, 1987. (d) Fetzer, J. C. Polycycl. Aromat. Comput. 1996, 11 (1-4), 317; (e) Diederich, F.; Rubin, Y. Angew. Chem. 1992, 104, 1123; Angew. Chem., Int. Ed. Engl. 1992, 31, 1101. (f) Hudgins, D. M.; Allamandola, L. J. J. Phys. Chem. 1995, 99, 3033. (g) Scott, L. T.; Cheng, P.-C.; Hashemi, M. M.; Bratcher, M. S.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1997, 119, 10963. (h) Faust, R. Angew. Chem. 1995, 107, 1559; Angew. Chem., Int. Ed. Engl. 1995, 34, 1429. (i) Müller, M.; Petersen, J.; Strohmaier, R.; Günther, C.; Karl, N.; Müllen, K. Angew. Chem. 1996, 108, 947; Angew. Chem., Int. Ed. Engl. 1996, 35, 886. (j) Tong, L.; Lau, H.; Ho, D. M.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1998, 120, 6000. (k) Debad, J. D.; Bard, A. J. J. Am. Chem. Soc. 1998, 120, 2476.
15. For further examples of extended polycyclic aromatic hydrocarbons, see: (a) Clar, E. Aromatische Kohlenwasserstoffe-Polycyclische Systeme; Springer, Berlin, 1952. (b) Clar, E. The Aromatic Sextet; Wiley: London, 1972. (c) Dias, J. R. Handbook of Polycyclic Hydrocarbons-Part a: Benzenoid Hydrocarbons; Elsevier: Amsterdam, 1987. (d) Fetzer, J. C. Polycycl. Aromat. Comput. 1996, 11 (1-4), 317; (e) Diederich, F.; Rubin, Y. Angew. Chem. 1992, 104, 1123; Angew. Chem., Int. Ed. Engl. 1992, 31, 1101. (f) Hudgins, D. M.; Allamandola, L. J. J. Phys. Chem. 1995, 99, 3033. (g) Scott, L. T.; Cheng, P.-C.; Hashemi, M. M.; Bratcher, M. S.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1997, 119, 10963. (h) Faust, R. Angew. Chem. 1995, 107, 1559; Angew. Chem., Int. Ed. Engl. 1995, 34, 1429. (i) Müller, M.; Petersen, J.; Strohmaier, R.; Günther, C.; Karl, N.; Müllen, K. Angew. Chem. 1996, 108, 947; Angew. Chem., Int. Ed. Engl. 1996, 35, 886. (j) Tong, L.; Lau, H.; Ho, D. M.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1998, 120, 6000. (k) Debad, J. D.; Bard, A. J. J. Am. Chem. Soc. 1998, 120, 2476.
16. For further examples of extended polycyclic aromatic hydrocarbons, see: (a) Clar, E. Aromatische Kohlenwasserstoffe-Polycyclische Systeme; Springer, Berlin, 1952. (b) Clar, E. The Aromatic Sextet; Wiley: London, 1972. (c) Dias, J. R. Handbook of Polycyclic Hydrocarbons-Part a: Benzenoid Hydrocarbons; Elsevier: Amsterdam, 1987. (d) Fetzer, J. C. Polycycl. Aromat. Comput. 1996, 11 (1-4), 317; (e) Diederich, F.; Rubin, Y. Angew. Chem. 1992, 104, 1123; Angew. Chem., Int. Ed. Engl. 1992, 31, 1101. (f) Hudgins, D. M.; Allamandola, L. J. J. Phys. Chem. 1995, 99, 3033. (g) Scott, L. T.; Cheng, P.-C.; Hashemi, M. M.; Bratcher, M. S.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1997, 119, 10963. (h) Faust, R. Angew. Chem. 1995, 107, 1559; Angew. Chem., Int. Ed. Engl. 1995, 34, 1429. (i) Müller, M.; Petersen, J.; Strohmaier, R.; Günther, C.; Karl, N.; Müllen, K. Angew. Chem. 1996, 108, 947; Angew. Chem., Int. Ed. Engl. 1996, 35, 886. (j) Tong, L.; Lau, H.; Ho, D. M.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1998, 120, 6000. (k) Debad, J. D.; Bard, A. J. J. Am. Chem. Soc. 1998, 120, 2476.
17. For further examples of extended polycyclic aromatic hydrocarbons, see: (a) Clar, E. Aromatische Kohlenwasserstoffe-Polycyclische Systeme; Springer, Berlin, 1952. (b) Clar, E. The Aromatic Sextet; Wiley: London, 1972. (c) Dias, J. R. Handbook of Polycyclic Hydrocarbons-Part a: Benzenoid Hydrocarbons; Elsevier: Amsterdam, 1987. (d) Fetzer, J. C. Polycycl. Aromat. Comput. 1996, 11 (1-4), 317; (e) Diederich, F.; Rubin, Y. Angew. Chem. 1992, 104, 1123; Angew. Chem., Int. Ed. Engl. 1992, 31, 1101. (f) Hudgins, D. M.; Allamandola, L. J. J. Phys. Chem. 1995, 99, 3033. (g) Scott, L. T.; Cheng, P.-C.; Hashemi, M. M.; Bratcher, M. S.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1997, 119, 10963. (h) Faust, R. Angew. Chem. 1995, 107, 1559; Angew. Chem., Int. Ed. Engl. 1995, 34, 1429. (i) Müller, M.; Petersen, J.; Strohmaier, R.; Günther, C.; Karl, N.; Müllen, K. Angew. Chem. 1996, 108, 947; Angew. Chem., Int. Ed. Engl. 1996, 35, 886. (j) Tong, L.; Lau, H.; Ho, D. M.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1998, 120, 6000. (k) Debad, J. D.; Bard, A. J. J. Am. Chem. Soc. 1998, 120, 2476.
18. For further examples of extended polycyclic aromatic hydrocarbons, see: (a) Clar, E. Aromatische Kohlenwasserstoffe-Polycyclische Systeme; Springer, Berlin, 1952. (b) Clar, E. The Aromatic Sextet; Wiley: London, 1972. (c) Dias, J. R. Handbook of Polycyclic Hydrocarbons-Part a: Benzenoid Hydrocarbons; Elsevier: Amsterdam, 1987. (d) Fetzer, J. C. Polycycl. Aromat. Comput. 1996, 11 (1-4), 317; (e) Diederich, F.; Rubin, Y. Angew. Chem. 1992, 104, 1123; Angew. Chem., Int. Ed. Engl. 1992, 31, 1101. (f) Hudgins, D. M.; Allamandola, L. J. J. Phys. Chem. 1995, 99, 3033. (g) Scott, L. T.; Cheng, P.-C.; Hashemi, M. M.; Bratcher, M. S.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1997, 119, 10963. (h) Faust, R. Angew. Chem. 1995, 107, 1559; Angew. Chem., Int. Ed. Engl. 1995, 34, 1429. (i) Müller, M.; Petersen, J.; Strohmaier, R.; Günther, C.; Karl, N.; Müllen, K. Angew. Chem. 1996, 108, 947; Angew. Chem., Int. Ed. Engl. 1996, 35, 886. (j) Tong, L.; Lau, H.; Ho, D. M.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1998, 120, 6000. (k) Debad, J. D.; Bard, A. J. J. Am. Chem. Soc. 1998, 120, 2476.
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