Synthesis and characterization of a C36H12 fullerene subunit

Journal of the American Chemical Society

Volumn 118, Issue 36, 1996, Pages 8743-8744

  Scott, Lawrence T ^a   Bratcher, Matthew S ^a   Hagen, Stefan ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FULLERENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0029835973     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9621511     Document Type: Article

References (43)

1. Krätschmer, W.; Lamb, L. D.; Fostiropoulos, K.; Huffman, D. R. Nature 1990, 347, 354-8.
2. For recent reviews on bowl-shaped fullerene subunits, see: Siegel, J. S.; Seiders, T. J. Chem. Britain 1995, 313-6. Faust, R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1429-32. Rabideau, P. W.; Sygula, A. Adv. Theor. Interesting Mol 1995, 3, 1-36. Rabideau, P. W.; Sygula, A. Acc. Chem. Res. 1996, 29, 235-42.
3. For recent reviews on bowl-shaped fullerene subunits, see: Siegel, J. S.; Seiders, T. J. Chem. Britain 1995, 313-6. Faust, R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1429-32. Rabideau, P. W.; Sygula, A. Adv. Theor. Interesting Mol 1995, 3, 1-36. Rabideau, P. W.; Sygula, A. Acc. Chem. Res. 1996, 29, 235-42.
4. For recent reviews on bowl-shaped fullerene subunits, see: Siegel, J. S.; Seiders, T. J. Chem. Britain 1995, 313-6. Faust, R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1429-32. Rabideau, P. W.; Sygula, A. Adv. Theor. Interesting Mol 1995, 3, 1-36. Rabideau, P. W.; Sygula, A. Acc. Chem. Res. 1996, 29, 235-42.
5. For recent reviews on bowl-shaped fullerene subunits, see: Siegel, J. S.; Seiders, T. J. Chem. Britain 1995, 313-6. Faust, R. Angew. Chem., Int. Ed. Engl. 1995, 34, 1429-32. Rabideau, P. W.; Sygula, A. Adv. Theor. Interesting Mol 1995, 3, 1-36. Rabideau, P. W.; Sygula, A. Acc. Chem. Res. 1996, 29, 235-42.
6. Barth, W. E.; Lawton, R. G. J. Am. Chem. Soc. 1966, 88, 380-1. Lawton, R. G.; Barth, W. E. J. Am. Chem. Soc. 1971, 93, 1730-45. Scott, L. T.; Hashemi, M. M.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1991, 113, 7082-4. Scott, L. T.; Cheng, P.-C.; Bratcher, M. S. Seventh International Symposium on Novel Aromatic Compounds, abstr. no. 64, Victoria, British Columbia, Canada, July 19-24, 1992. Cheng, P.-C. M. S. thesis, University of Nevada, Reno, 1992. Borchardt, A.; Fuchicello, A.; Kilway, K. V.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 1921-3. Zimmermann, G.; Nuechter, U.; Hagen, S.; Nuechter, M. Tetrahedron Lett. 1994, 35, 4747-50.
7. Barth, W. E.; Lawton, R. G. J. Am. Chem. Soc. 1966, 88, 380-1. Lawton, R. G.; Barth, W. E. J. Am. Chem. Soc. 1971, 93, 1730-45. Scott, L. T.; Hashemi, M. M.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1991, 113, 7082-4. Scott, L. T.; Cheng, P.-C.; Bratcher, M. S. Seventh International Symposium on Novel Aromatic Compounds, abstr. no. 64, Victoria, British Columbia, Canada, July 19-24, 1992. Cheng, P.-C. M. S. thesis, University of Nevada, Reno, 1992. Borchardt, A.; Fuchicello, A.; Kilway, K. V.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 1921-3. Zimmermann, G.; Nuechter, U.; Hagen, S.; Nuechter, M. Tetrahedron Lett. 1994, 35, 4747-50.
8. Barth, W. E.; Lawton, R. G. J. Am. Chem. Soc. 1966, 88, 380-1. Lawton, R. G.; Barth, W. E. J. Am. Chem. Soc. 1971, 93, 1730-45. Scott, L. T.; Hashemi, M. M.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1991, 113, 7082-4. Scott, L. T.; Cheng, P.-C.; Bratcher, M. S. Seventh International Symposium on Novel Aromatic Compounds, abstr. no. 64, Victoria, British Columbia, Canada, July 19-24, 1992. Cheng, P.-C. M. S. thesis, University of Nevada, Reno, 1992. Borchardt, A.; Fuchicello, A.; Kilway, K. V.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 1921-3. Zimmermann, G.; Nuechter, U.; Hagen, S.; Nuechter, M. Tetrahedron Lett. 1994, 35, 4747-50.
9. Barth, W. E.; Lawton, R. G. J. Am. Chem. Soc. 1966, 88, 380-1. Lawton, R. G.; Barth, W. E. J. Am. Chem. Soc. 1971, 93, 1730-45. Scott, L. T.; Hashemi, M. M.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1991, 113, 7082-4. Scott, L. T.; Cheng, P.-C.; Bratcher, M. S. Seventh International Symposium on Novel Aromatic Compounds, abstr. no. 64, Victoria, British Columbia, Canada, July 19-24, 1992. Cheng, P.-C. M. S. thesis, University of Nevada, Reno, 1992. Borchardt, A.; Fuchicello, A.; Kilway, K. V.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 1921-3. Zimmermann, G.; Nuechter, U.; Hagen, S.; Nuechter, M. Tetrahedron Lett. 1994, 35, 4747-50.
10. Barth, W. E.; Lawton, R. G. J. Am. Chem. Soc. 1966, 88, 380-1. Lawton, R. G.; Barth, W. E. J. Am. Chem. Soc. 1971, 93, 1730-45. Scott, L. T.; Hashemi, M. M.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1991, 113, 7082-4. Scott, L. T.; Cheng, P.-C.; Bratcher, M. S. Seventh International Symposium on Novel Aromatic Compounds, abstr. no. 64, Victoria, British Columbia, Canada, July 19-24, 1992. Cheng, P.-C. M. S. thesis, University of Nevada, Reno, 1992. Borchardt, A.; Fuchicello, A.; Kilway, K. V.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 1921-3. Zimmermann, G.; Nuechter, U.; Hagen, S.; Nuechter, M. Tetrahedron Lett. 1994, 35, 4747-50.
11. Barth, W. E.; Lawton, R. G. J. Am. Chem. Soc. 1966, 88, 380-1. Lawton, R. G.; Barth, W. E. J. Am. Chem. Soc. 1971, 93, 1730-45. Scott, L. T.; Hashemi, M. M.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1991, 113, 7082-4. Scott, L. T.; Cheng, P.-C.; Bratcher, M. S. Seventh International Symposium on Novel Aromatic Compounds, abstr. no. 64, Victoria, British Columbia, Canada, July 19-24, 1992. Cheng, P.-C. M. S. thesis, University of Nevada, Reno, 1992. Borchardt, A.; Fuchicello, A.; Kilway, K. V.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 1921-3. Zimmermann, G.; Nuechter, U.; Hagen, S.; Nuechter, M. Tetrahedron Lett. 1994, 35, 4747-50.
12. Barth, W. E.; Lawton, R. G. J. Am. Chem. Soc. 1966, 88, 380-1. Lawton, R. G.; Barth, W. E. J. Am. Chem. Soc. 1971, 93, 1730-45. Scott, L. T.; Hashemi, M. M.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1991, 113, 7082-4. Scott, L. T.; Cheng, P.-C.; Bratcher, M. S. Seventh International Symposium on Novel Aromatic Compounds, abstr. no. 64, Victoria, British Columbia, Canada, July 19-24, 1992. Cheng, P.-C. M. S. thesis, University of Nevada, Reno, 1992. Borchardt, A.; Fuchicello, A.; Kilway, K. V.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 1921-3. Zimmermann, G.; Nuechter, U.; Hagen, S.; Nuechter, M. Tetrahedron Lett. 1994, 35, 4747-50.
13. Cyclopenta[bc]corannulene: Abdourazak, A. H.; Sygula, A.; Rabideau, P. W. J. Am. Chem. Soc. 1993, 115, 3010-11. Sygula, A.; Abdourazak, A. H.; Rabideau, P. W. J. Am. Chem. Soc. 1996, 118, 339-43. Cheng, P.-C. Ph.D. Dissertation, Boston College, 1996.
14. Cyclopenta[bc]corannulene: Abdourazak, A. H.; Sygula, A.; Rabideau, P. W. J. Am. Chem. Soc. 1993, 115, 3010-11. Sygula, A.; Abdourazak, A. H.; Rabideau, P. W. J. Am. Chem. Soc. 1996, 118, 339-43. Cheng, P.-C. Ph.D. Dissertation, Boston College, 1996.
15. Cyclopenta[bc]corannulene: Abdourazak, A. H.; Sygula, A.; Rabideau, P. W. J. Am. Chem. Soc. 1993, 115, 3010-11. Sygula, A.; Abdourazak, A. H.; Rabideau, P. W. J. Am. Chem. Soc. 1996, 118, 339-43. Cheng, P.-C. Ph.D. Dissertation, Boston College, 1996.
16. Benzocorannulene and cyclopenta[kl]dibenzo[a,g]corannulene: Scott, L. T.; McComas, C. C. results presented at the National Meeting of the American Chemical Society, New Orleans, LA, March, 1996. McComas, C. C. B.S. Thesis, Boston College, 1996.
17. Benzocorannulene and cyclopenta[kl]dibenzo[a,g]corannulene: Scott, L. T.; McComas, C. C. results presented at the National Meeting of the American Chemical Society, New Orleans, LA, March, 1996. McComas, C. C. B.S. Thesis, Boston College, 1996.
18. Diindeno[1,2,3,4-defg; 1′,2′,3′,4′-mnop]chrysene: Hagen, S.; Nuechter, U.; Nuechter, M.; Zimmermann, G. Polycyclic Arom. Comp. 1995, 4, 209-17. Scott, L. T.; Choi, N.; Bronstein, H. Unpublished results.
19. Diindeno[1,2,3,4-defg; 1′,2′,3′,4′-mnop]chrysene: Hagen, S.; Nuechter, U.; Nuechter, M.; Zimmermann, G. Polycyclic Arom. Comp. 1995, 4, 209-17. Scott, L. T.; Choi, N.; Bronstein, H. Unpublished results.
20. Dibenzo[a,g]corannulene: Scott, L. T.; Bratcher, M. S. results presented at the National Meeting of the American Chemical Society, San Diego, CA, March. 1994. Bratcher, M. S. Ph.D. Dissertation, Boston College, 1996.
21. Dibenzo[a,g]corannulene: Scott, L. T.; Bratcher, M. S. results presented at the National Meeting of the American Chemical Society, San Diego, CA, March. 1994. Bratcher, M. S. Ph.D. Dissertation, Boston College, 1996.
22. Rabideau, P. W.; Abdourazak, A. H.; Folsom, H. J. Am. Chem. Soc. 1994, 116, 7891-2. Abdourazak, A. H.; Marcinow, Z.; Sygula, A.; Sygula, R.; Rabideau, P. W. J. Am. Chem. Soc. 1995, 117, 6410-11.
23. Rabideau, P. W.; Abdourazak, A. H.; Folsom, H. J. Am. Chem. Soc. 1994, 116, 7891-2. Abdourazak, A. H.; Marcinow, Z.; Sygula, A.; Sygula, R.; Rabideau, P. W. J. Am. Chem. Soc. 1995, 117, 6410-11.
24. The complete name for 1 is triacenaphtho[3.2,1,8-c,d,e,f,g; 3′,2′,1′,8′-i,j,k,l,m; 3″,2″,1″,8″-o,pq,r,a]triphenylene.
25. Rehländer, P. Ph.D. dissertation, University of Berlin, 1893, cited by Rehländer, P. Chem. Ber. 1903, 36, 1583-7. Dziewonski, K. Chem. Ber. 1903, 36, 962-71. Ho, D. M.; Pascal, R. A. Chem. Mater. 1993, 5, 1358-61.
26. Rehländer, P. Ph.D. dissertation, University of Berlin, 1893, cited by Rehländer, P. Chem. Ber. 1903, 36, 1583-7. Dziewonski, K. Chem. Ber. 1903, 36, 962-71. Ho, D. M.; Pascal, R. A. Chem. Mater. 1993, 5, 1358-61.
27. Rehländer, P. Ph.D. dissertation, University of Berlin, 1893, cited by Rehländer, P. Chem. Ber. 1903, 36, 1583-7. Dziewonski, K. Chem. Ber. 1903, 36, 962-71. Ho, D. M.; Pascal, R. A. Chem. Mater. 1993, 5, 1358-61.
28. Rehländer, P. Ph.D. dissertation, University of Berlin, 1893, cited by Rehländer, P. Chem. Ber. 1903, 36, 1583-7. Dziewonski, K. Chem. Ber. 1903, 36, 962-71. Ho, D. M.; Pascal, R. A. Chem. Mater. 1993, 5, 1358-61.
29. Decacyclene is currently available for $120.85/500 g from Aldrich Chemical Co., Milwaukee, WI.
30. 14 product of double ring closure (3) eluting in that order.
31. The high mobility of bowl-shaped polycyclic aromatic hydrocarbons on alumina chromatography, relative to that of planar PAH of comparable size, has previously been noted: Hagen, S.; Christoph, H.: Zimmermann, G. Tetrahedron 1995, 51, 6961-70. Similar behavior on reverse phase HPLC has likewise been reported: Sander, L. C.; Wise, S. A. J. Chromatogr. 1993, 97, 13539-43. Fetzer, J. C.; Biggs, W. R.; Jinno, K. Chromatogr. 1986, 21, 439-42.
32. The high mobility of bowl-shaped polycyclic aromatic hydrocarbons on alumina chromatography, relative to that of planar PAH of comparable size, has previously been noted: Hagen, S.; Christoph, H.: Zimmermann, G. Tetrahedron 1995, 51, 6961-70. Similar behavior on reverse phase HPLC has likewise been reported: Sander, L. C.; Wise, S. A. J. Chromatogr. 1993, 97, 13539-43. Fetzer, J. C.; Biggs, W. R.; Jinno, K. Chromatogr. 1986, 21, 439-42.
33. The high mobility of bowl-shaped polycyclic aromatic hydrocarbons on alumina chromatography, relative to that of planar PAH of comparable size, has previously been noted: Hagen, S.; Christoph, H.: Zimmermann, G. Tetrahedron 1995, 51, 6961-70. Similar behavior on reverse phase HPLC has likewise been reported: Sander, L. C.; Wise, S. A. J. Chromatogr. 1993, 97, 13539-43. Fetzer, J. C.; Biggs, W. R.; Jinno, K. Chromatogr. 1986, 21, 439-42.
34. max (ε): 368 (sh, 4000), 322 (sh, 16 000), 290.5 (25 000), 232.5 (37 000).
35. Semiempirical molecular orbital calculations were performed using the Spartan program, version 4.0 from Wavefunction, Inc., Irvine CA.
36. Haddon, R. C.; Scott, L. T. Pure Appl. Chem. 1986, 58, 137-42. Haddon, R. C. J. Am. Chem. Soc. 1990, 112, 3385-9. We thank Dr. Haddon for kindly supplying a copy of the POAV program.
37. Haddon, R. C.; Scott, L. T. Pure Appl. Chem. 1986, 58, 137-42. Haddon, R. C. J. Am. Chem. Soc. 1990, 112, 3385-9. We thank Dr. Haddon for kindly supplying a copy of the POAV program.
38. max (ε): 460 (sh, 2100), 387 (11 100), 373 (11 500), 359 (11 100), 323 (59 100), 242 (sh 57 000), 228 (60 500).
39. max (ε): 497 (8800), 464 (7200), 390 (29 600), 377 (27 000), 358 (29 300, sh), 343 (47 900), 329 (38 200, sh), 286 (97 900), 238 nm (76 400, sh).
40. Gerhardt, Ph.; Löffler, S.; Homann, K.-H. Chem. Phys. Lett. 1988, 88, 1588. Howard, J. B.; Lafleur, A. L.; Makarovsky, Y.; Mitra, S.; Pope, C. J.; Yadav, T. K. Carbon 1992, 30, 1183-201. Pope, C. J.; Marr, J. A.; Howard, J. B. J. Phys. Chem. 1993, 97, 11001-13. Ahrens, J.; Bachmann, M.; Baum, Th.; Griesheimer, J., Kovacs, R.; Weilmünster, P.; Homann, K.-H. Internat. J. Mass Spectr. Ion Proc. 1994, 138, 133-48 and references cited therein.
41. Gerhardt, Ph.; Löffler, S.; Homann, K.-H. Chem. Phys. Lett. 1988, 88, 1588. Howard, J. B.; Lafleur, A. L.; Makarovsky, Y.; Mitra, S.; Pope, C. J.; Yadav, T. K. Carbon 1992, 30, 1183-201. Pope, C. J.; Marr, J. A.; Howard, J. B. J. Phys. Chem. 1993, 97, 11001-13. Ahrens, J.; Bachmann, M.; Baum, Th.; Griesheimer, J., Kovacs, R.; Weilmünster, P.; Homann, K.-H. Internat. J. Mass Spectr. Ion Proc. 1994, 138, 133-48 and references cited therein.
42. Gerhardt, Ph.; Löffler, S.; Homann, K.-H. Chem. Phys. Lett. 1988, 88, 1588. Howard, J. B.; Lafleur, A. L.; Makarovsky, Y.; Mitra, S.; Pope, C. J.; Yadav, T. K. Carbon 1992, 30, 1183-201. Pope, C. J.; Marr, J. A.; Howard, J. B. J. Phys. Chem. 1993, 97, 11001-13. Ahrens, J.; Bachmann, M.; Baum, Th.; Griesheimer, J., Kovacs, R.; Weilmünster, P.; Homann, K.-H. Internat. J. Mass Spectr. Ion Proc. 1994, 138, 133-48 and references cited therein.
43. Gerhardt, Ph.; Löffler, S.; Homann, K.-H. Chem. Phys. Lett. 1988, 88, 1588. Howard, J. B.; Lafleur, A. L.; Makarovsky, Y.; Mitra, S.; Pope, C. J.; Yadav, T. K. Carbon 1992, 30, 1183-201. Pope, C. J.; Marr, J. A.; Howard, J. B. J. Phys. Chem. 1993, 97, 11001-13. Ahrens, J.; Bachmann, M.; Baum, Th.; Griesheimer, J., Kovacs, R.; Weilmünster, P.; Homann, K.-H. Internat. J. Mass Spectr. Ion Proc. 1994, 138, 133-48 and references cited therein.