Peralkylated Coronenes via Regiospecific Hydrogenation of Hexa-peri-hexabenzocoronenes

Journal of the American Chemical Society

Volumn 126, Issue 3, 2004, Pages 766-771

  Watson, Mark D ^a,c   Debije, Michael G ^b   Warman, John M ^b   Müllen, Klaus ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

^b DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

^c UNIVERSITY OF KENTUCKY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; ALKYLATION; CHARGE CARRIERS; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEATION; THERMAL EFFECTS; ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION ANALYSIS;

HETERONUCLEAR CORRELATION; ISOTROPIZATION;

BIOCHEMISTRY;

ALKYL GROUP; AROMATIC HYDROCARBON; BENZENE DERIVATIVE; CORONENE DERIVATIVE; HEXAPERIHEXABENZOCORONENE DERIVATIVE; HYDROGEN; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONDUCTANCE; CONFORMATIONAL TRANSITION; ELECTRIC POTENTIAL; HEAT TREATMENT; HYDROGENATION; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MEASUREMENT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRESSURE; PROTON NUCLEAR MAGNETIC RESONANCE; PULSE RADIOLYSIS; QUANTITATIVE ANALYSIS; REACTION ANALYSIS; SOLUBILITY; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ANALYSIS; SYNTHESIS; TEMPERATURE DEPENDENCE; ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION;

EID: 1642576000     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja037522+     Document Type: Article

References (38)

1. Donohoe, T. J.; Garg, R.; Stevenson, C. A. Tetrahedron: Assymetry 1996, 7, 317.
2. Rothwell, I. Chem. Commun. 1997 1331-38.
3. Harvey, R. J. Polycyclic Aromatic Hydrocarbons; VCH: New York, 1997; Chapter 4.
4. Yalpani, M.; Köster, R. Chem. Ber. 1990, 123, 719-24.
5. Applied Homogeneous Catalysis with Organometallic Compounds; Cornills, B., Herrmann, W. A., Eds.; VCH: New York, 1996; Vol. 1.
6. Clar, E. The Aromatic Sextet: John Wiley and Sons: London, 1972.
7. German patent application no. 102 55 363.7.
8. Fischbach, I.; Pakula, T.; Minkin, P.; Fechtenkötter, A.; Müllen, K.; Spiess, H. W.; Saalwächter, K. J. Phys. Chem. B. 2002, 106, 6408-18.
9. (a) Samorí, P.; Fechtenkötter, A.; Böhme, T.; Jäckel, F.; Müllen, K.; Rabe, J. P. J. Am. Chem. Soc. 2001. 123, 11462-67.
10. (b) Tchebotareva, N.; Yin, X.; Watson, M. D.; Samorí, P.; Rabe, J. P.; Müllen, K. J. Am. Chem. Soc. 2003, 125, 9734-39.
11. Goddard, R.; Hänel, M.; Herndon, W. C.; Krüger, C.; Zander, M. J. Am. Chem. Soc. 1995, 117, 30-41.
12. Samorí, P.; Severin, N.; Simpson, C. D.; Müllen, K.; Rabe, J. P. J. Am. Chem. Soc. 2002, 124, 9454-57.
13. Fromherz, H.; Thaler, L.; Wolf, G. Z. Elektrochem. 1943, 49, 387-400.
14. Silverstein, R. M.; Bassler, C. G.; Morrill, T. C. Spectrometric Identification of Organic Compounds, 5th ed.; Wiley: New York, 1991; pp 208-9.
15. 2, was added (good solvent for breaking π-π contacts), significant red shift in luminescence on changing solvents and concentration, fiber formation from solution, etc.
16. Fu, P. F.; Lee, H. M.; Harvey, R. G. J. Org. Chem. 1980, 45, 2797-2803.
17. Moran, D.; Stahl, F.; Bettinger, H. F.; Schäfer, H. F., III; Schleyer, P. v. R. J. Am. Chem. Soc. 2003, 125, 6746-52.
18. Zhou, Z. X. J. Phys. Org. Chem. 1995, 8, 103-07.
19. Farina, M. Tetrahedron Lett. 1963, 2097-2100. Farina, M.; Di Silvestro, G.; Sozzani, P. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., Macnicol, D. D., Vögtle, F., Eds.; Pergamon Press: Oxford, 1996; Vol. 6, Chapter 12.
20. Farina, M. Tetrahedron Lett. 1963, 2097-2100. Farina, M.; Di Silvestro, G.; Sozzani, P. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., Macnicol, D. D., Vögtle, F., Eds.; Pergamon Press: Oxford, 1996; Vol. 6, Chapter 12.
21. Much like their precursors, a common problem with substituted discotic molecules. See, for example: Bushby, R. J.; Boden, N.; Kilner, C. A.; Lozman, O. R.; Lu, Z.; Quanying, L.; Thornton-Pett, M. A. J. Mater. Chem. 2003, 13, 470-74.
22. Baird, T.; Gall, J. H.; Macnicol, D. D.; Mallinson, P. R.; Michie, C. R. J. Chem. Soc., Chem. Commun. 1988, 1471-73. Frampton, C. S.; MacNicol, D. D.; Rowan, S. J. J. Mol. Struct. 1997, 405, 169-78. Shibata, K.; Kulkarni, A. A.; Ho, D. M.; Pascal, R. A., Jr. J. Org. Chem. 1995, 60, 428-34. Downing, G. A.; Frampton, C. S.; MacNicol, D. D.; Mallinson, P. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1587-89.
23. Baird, T.; Gall, J. H.; Macnicol, D. D.; Mallinson, P. R.; Michie, C. R. J. Chem. Soc., Chem. Commun. 1988, 1471-73. Frampton, C. S.; MacNicol, D. D.; Rowan, S. J. J. Mol. Struct. 1997, 405, 169-78. Shibata, K.; Kulkarni, A. A.; Ho, D. M.; Pascal, R. A., Jr. J. Org. Chem. 1995, 60, 428-34. Downing, G. A.; Frampton, C. S.; MacNicol, D. D.; Mallinson, P. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1587-89.
24. Baird, T.; Gall, J. H.; Macnicol, D. D.; Mallinson, P. R.; Michie, C. R. J. Chem. Soc., Chem. Commun. 1988, 1471-73. Frampton, C. S.; MacNicol, D. D.; Rowan, S. J. J. Mol. Struct. 1997, 405, 169-78. Shibata, K.; Kulkarni, A. A.; Ho, D. M.; Pascal, R. A., Jr. J. Org. Chem. 1995, 60, 428-34. Downing, G. A.; Frampton, C. S.; MacNicol, D. D.; Mallinson, P. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1587-89.
25. Baird, T.; Gall, J. H.; Macnicol, D. D.; Mallinson, P. R.; Michie, C. R. J. Chem. Soc., Chem. Commun. 1988, 1471-73. Frampton, C. S.; MacNicol, D. D.; Rowan, S. J. J. Mol. Struct. 1997, 405, 169-78. Shibata, K.; Kulkarni, A. A.; Ho, D. M.; Pascal, R. A., Jr. J. Org. Chem. 1995, 60, 428-34. Downing, G. A.; Frampton, C. S.; MacNicol, D. D.; Mallinson, P. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1587-89.
26. Macnicol, D. D.; Downing, G. A. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., Macnicol, D. D., Vögtle, F., Eds.; Pergamon Press: Oxford, 1996; Vol. 6, Chapter 14.
27. van de Craats, A. M.; Warman, J. M. Adv. Mater. 2001, 13, 130-33.
28. Supporting Information.
29. Similar to other discotics, WAXD measurements indicate that the rigid molecular cores are "crystallized" at room temperature but the side chains may be liquidlike or partially crystallized. The room temperature phases may be plastically deformed to give aligned, optically clear films/fibers.
30. Fechtenkötter, A.; Tchebotareva, N.; Watson, K.; Müllen, K. Tetrahedron 2001, 57, 3769-3783 and references therein.
31. Liu, C.-Y.; Bard, A. J. Chem. Mater. 2000, 12, 2353-62. Cooling of isotropic thin films along a heat gradient or on Teflon alignment layers results in alignment of columns parallel to the surface as indicated by POM.
32. Liu, C.-Y.; Bard, A. J. Nature 2002, 418, 162-64.
33. (a) Bunk, O.; Nielsen, M. M.; Sølling, T. I.; van de Craats, A. M.; Stutzmann, N. J. Am. Chem. Soc. 2003, 125, 2252-58.
34. (b) van de Craats, A. M.; Stutzmann, N.; Bunk, O.; Nielsen, M. M.; Watson, M. D.; Müllen, K.; Chanzy, H. D.; Sirringhaus, H.; Friend, R. H. Adv. Mater. 2003, 15, 495-99.
35. van de Craats, A. M.; Warman, J. M.; Fechtenkötter, A.; Brand, J. D.; Harbison, M. A.; Müllen, K. Adv. Mater. 1999, 11, 1469-1472.
36. Tracz, A.; Wostek, D.; Kucinska, I.; Jeszka, J. K.; Watson, M.; Müllen, K.; Pakula, T. In NATO ASI Series; Graja, A., Bulka, B. R., Kajzar, F., Eds.; Kluwer Academic Publishers: Dordrecht, 2002; pp 315-318.
37. Iyer, V. S.; Yoshimura, K.; Enkelmann, V.; Epsch, R.; Rabe, J. P.; Müllen, K. Angew. Chem., Int. Ed. 1998, 37, 2696-99.
38. Simpson, C. D. Nanoscale Polycyclic Aromatic Hydrocarbons-Synthesis and Characterization. Ph.D. Dissertation, Johannes Gutenberg University, Mainz, 2003.