Synthesis, structures, and solid state self-assemblies of formyl and acetyl substituted triptycenes and their derivatives

Journal of Organic Chemistry

Volumn 77, Issue 20, 2012, Pages 9250-9259

  Li, Peng Fei ^a,b   Chen, Chuan Feng ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2D LAYER; ALDOXIMES; AMIDE GROUPS; AROMATIC RINGS; BAEYER VILLIGER OXIDATION; BECKMANN REARRANGEMENT; CYCLOTRIMERIZATION; DEACETYLATION; DERIVATIZATIONS; FUNCTIONALIZED; HIGH YIELD; HYDROGEN BOND NETWORKS; MICROPOROUS; POROUS STRUCTURES; REGIOISOMERS; SELF-ASSEMBLE; SINGLE CRYSTAL X-RAY ANALYSIS; TRIPTYCENES;

ACETYLATION; AMIDES; D REGION; DEHYDRATION; HYDROGEN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY ANALYSIS;

SYNTHESIS (CHEMICAL);

1,3,5 TRITRIPTYCENEBENZENE; 2 ACETYLTRIPTYCENE; 2 ETHYNYLTRIPTYCENE; 2 FORMYLTRIPTYCENE; 2,6 DIACETYLTRIPTYCENE; 2,6 DIFORMYLTRIPTYCENE; 2,6,14 TRIACETAMINOTRIPTYCENE; 2,6,14 TRIACETYLTRIPTYCENE; 2,7 DIACETYLTRIPTYCENE; 2,7 DIFORMYLTRIPTYCENE; 2,7,14 TRIACETAMINOTRIPTYCENE; 2,7,14 TRIACETYLTRIPTYCENE; ALDOXIME; TRIACETAMINOTRIPTYCENE; TRIPTYCENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BAEYER VILLIGER REACTION; BECKMANN REARRANGEMENT; CARBON NUCLEAR MAGNETIC RESONANCE; DEACETYLATION; DEHYDRATION; HYDROGEN BOND; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; SYNTHESIS; X RAY ANALYSIS;

ANTHRACENES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84867724808     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301820v     Document Type: Article

References (53)

1. Chen, C.-F. Chem. Commun. 2011, 47, 1674 and references therein
2. Jiang, Y.; Chen, C.-F. Eur. J. Org. Chem. 2011, 32, 6377
3. Chen, C.-F.; Han, T.; Jiang, Y. Chin. Sci. Bull. 2007, 52, 1349
4. Kelly, T. R.; Cai, X.; Damkaci, F.; Panicker, S. B.; Tu, B.; Bushell, S. M.; Cornella, I.; Piggott, M. J.; Salives, R.; Cavero, M.; Zhao, Y.; Jasmin, S. J. Am. Chem. Soc. 2007, 129, 376
5. Nikitin, K.; Müller-Bunz, H.; Ortin, Y.; McGlinchey, M. J. Chem.-Eur. J. 2009, 15, 1836
6. Garcia-Garibay, M. A.; Godinez, C. E. Cryst. Growth Des. 2009, 9, 3124
7. Nikitin, K.; Müller-Bunz, H.; Ortin, Y.; Muldoon, J.; McGlinchey, M. J. J. Am. Chem. Soc. 2010, 132, 17617
8. Jiang, Y.; Guo, J.-B.; Chen, C.-F. Org. Lett. 2010, 12, 4248
9. Yang, J.-S.; Huang, Y.-T.; Ho, J.-H.; Sun, W.-T.; Huang, H.-H.; Lin, Y.-C.; Huang, S.-J.; Huang, S.-L.; Lu, H.-F.; Chao, I. Org. Lett. 2008, 10, 2279
10. Sun, W.-T.; Huang, Y.-T.; Huang, G.-J.; Lu, H.-F.; Chao, I.; Huang, S.-L.; Huang, S.-J.; Lin, Y.-C.; Ho, J.-H.; Yang, J.-S. Chem.-Eur. J. 2011, 17, 1193
11. Sun, W.-T.; Huang, Y.-T.; Huang, G.-J.; Lu, H.-F.; Chao, I.; Huang, S.-L.; Huang, S.-J.; Lin, Y.-C.; Ho, J.-H.; Yang, J.-S. Chem.-Eur. J. 2010, 16, 11594
12. Kao, C.-Y.; Hsu, Y.-T.; Lu, H.-F.; Chao, I.; Huang, S.-L.; Lin, Y.-C.; Sun, W.-T.; Yang, J.-S. J. Org. Chem. 2011, 76, 5782
13. Frantz, D. K.; Linden, A.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 2012, 134, 1528
14. Swager, T. M. Acc. Chem. Res. 2008, 41, 1181
15. Yang, J. S.; Yan, J. L. Chem. Commun. 2008, 13, 1501
16. Chong, J. H.; MacLachlan, M. J. Chem. Soc. Rev. 2009, 38, 3301
17. Hoogboom, J.; Swager, T. M. J. Am. Chem. Soc. 2006, 128, 15058
18. Hilton, C. L.; Jamison, C. R.; Zane, H. K.; King, B. T. J. Org. Chem. 2009, 74, 705
19. Chen, Z.; Swager, T. M. Macromolecules 2008, 41, 6880
20. Ghanem, B. S.; Hashem, M.; Harris, K. D. M.; Msayib, K. J.; Xu, M.; Budd, P. M.; Chaukura, N.; Book, D.; Tedds, S.; Walton, A.; McKeown, N. B. Macromolecules 2010, 43, 5287
21. Chong, J. H.; Ardakani, S. J.; Smith, K. J.; MacLachlan, M. J. Chem.-Eur. J. 2009, 15, 11824
22. Chou, H.-H.; Shih, H.-H.; Cheng, Ch.-H. J. Mater. Chem. 2010, 20, 798
23. Goldsmith, R. H.; Vura-Weis, J.; Scott, A. M.; Borkar, S.; Sen, A.; Ratner, M. A.; Wasielewski, M. R. J. Am. Chem. Soc. 2008, 130, 7659
24. Gu, X.; Lai, Y.-H. Org. Lett. 2010, 12, 5200
25. VanVeller, B.; Robinson, D.; Swager, T. M. Angew. Chem., Int. Ed. 2011, 50, 1182
26. Mati, I. K.; Cockroft, S. L. Chem. Soc. Rev. 2010, 39, 4195
27. Hua, D. H.; Lou, K.; Battina, S. K.; Zhao, H.; Perchellet, E. M.; Wang, Y.; Perchellet, J.-P. H. Anti-Cancer Agents Med. Chem. 2006, 6, 303
28. Zhao, L.-W.; Li, Z.; Wirth, T. Chem. Lett. 2010, 39, 658
29. Chong, J. H.; MacLachlan, M. J. Inorg. Chem. 2006, 45, 1442
30. Chong, J. H.; MacLachlan, M. J. J. Org. Chem. 2007, 72, 8683
31. Bini, L.; Müller, C.; Wilting, J.; Chrzanowski, L.; Spek, A. L.; Vogt, D. J. Am. Chem. Soc. 2007, 129, 12622
32. Grossman, O.; Gelman, D. Org. Lett. 2006, 8, 1189
33. Gung, B. W.; Wekesa, F.; Barnes, C. L. J. Org. Chem. 2008, 73, 1803
34. Gung, B. W.; Zou, Y.; Xu, Z.; Amicangelo, J. C.; Irwin, D. G.; Ma, S.; Zhou, H.-C. J. Org. Chem. 2008, 73, 689
35. Gung, B. W.; Emenike, B. U.; Lewis, M.; Kirschbaum, K. Chem.-Eur. J. 2010, 16, 12357
36. Roy, X.; Chong, J. H.; Patrick, B. O.; MacLachlan, M. J. Cryst. Growth Des. 2011, 11, 4551
37. Wittig, G.; Stilz, W.; Knauss, E. Angew. Chem. 1958, 70, 166
38. Stiles, M.; G. Miller, R. J. Am. Chem. Soc. 1960, 82, 3802
39. Zhang, C.; Chen, C.-F. J. Org. Chem. 2006, 71, 6626
40. Zhang, C.; Chen, C.-F. J. Org. Chem. 2007, 72, 9339
41. Zhang, C.; Liu, Y.; Li, B.; Tan, B.; Chen, C.-F.; Xu, H.-B.; Yang, X.-L. ACS Macro Lett. 2012, 1, 190
42. Paget, C. J.; Burger, A. J. Org. Chem. 1965, 30, 1329
43. Skvarchenko, V. R.; Lapteva, V. L.; Sereda, G. A. J. Org. Chem. USSR 1991, 27, 1747
44. Sereda, G. A.; Skvarchenko, V. R. Russ. J. Org. Chem. 1994, 30, 442
45. Sereda, G. A.; Lapteva, V. L.; Skvarchenko, V. R. Russ. J. Org. Chem. 1994, 30, 1137
46. Chakrabarti, J. K.; Hotten, T. M. J. Chem. Soc., Chem. Commun. 1972, 1226
47. Luca, L. D.; Giacomelli, G.; Porcheddu, A. J. Org. Chem. 2002, 67, 6272
48. Zhang, C.; Chen, C.-F. J. Org. Chem. 2007, 72, 3880
49. Xue, M.; Chen, C.-F. Chem. Commun. 2008, 46, 6128
50. Ramalingan, C.; Park, Y.-T. J. Org. Chem. 2007, 72, 4536
51. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 13, 3769
52. Elmorsy, S. S.; Pelter, A.; Smith, K. Tetrahedron Lett. 1991, 32, 4175
53. Fabris, F.; Zonta, C.; Borsato, G.; De Lucchi, O. Acc. Chem. Res. 2011, 44, 416