Complementary helicity interchange of optically switchable supramolecular-enantiomeric helicenes with (-)-gel-sol-(+)-gel transition ternary logic

Journal of the American Chemical Society

Volumn 135, Issue 14, 2013, Pages 5294-5297

  Chen, Chien Tien ^a   Chen, Chien Hsiang ^b   Ong, Tiow Gan ^c  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^b NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

^c INSTITUTE OF CHEMISTRY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

GEL TRANSITIONS; H-BONDING; HELICENES; HELICITIES; INTERCONVERSIONS; SELF-ASSEMBLE; SWITCHABLE; TERNARY LOGIC;

CHEMISTRY; SYNTHESIS (CHEMICAL);

SOLS;

ALKYL GROUP; DIMETHOXYMETHYL DIBENZOSUBERANE; HELICENE; POLYCYCLIC AROMATIC COMPOUND; TRICYCLIC AROMATIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; DIASTEREOISOMER; ENANTIOMER; HYDROGEN BOND; ISOMERIZATION; QUANTUM YIELD; SIMULATION; ULTRAVIOLET RADIATION;

AMIDES; GELS; HYDROGEN BONDING; MACROMOLECULAR SUBSTANCES; METHYLENE CHLORIDE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OPTICAL PROCESSES; PARTICLE SIZE; STEREOISOMERISM; SURFACE PROPERTIES;

EID: 84876034852     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja401214t     Document Type: Article

References (50)

1. Feringa, B. L.; Van Delden, R. A. Angew. Chem., Int. Ed. 1999, 38, 3418
2. Schulz, G. E.; Schirmer, R. H. Principles of Protein Structure; Springer: New York, 1979.
3. Saenger, W. Principles of Nucleic Acid Structure; Springer: New York, 1984.
4. Weiss, R. G.; David, J. A. Adv. Mater. 2000, 12, 1237
5. Terech, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133
6. Gronwald, O.; Shinkai, S. Chem.-Eur. J. 2001, 7, 4328
7. Van Esch, J. H.; Feringa, B. L. Angew. Chem., Int. Ed. 2000, 39, 2263
8. Lin, Y.; Kachar, B.; Weiss, R. G. J. Am. Chem. Soc. 1989, 111, 5542
9. Fenniri, H.; Mathivanan, P.; Vidale, K. L.; Sherman, D. M.; Hallenga, K.; Wood, K. V.; Stowell, J. G. J. Am. Chem. Soc. 2001, 123, 3854
10. Nakayama, D.; Takeoka, Y.; Watanabe, M.; Kataoka, K. Angew. Chem., Int. Ed. 2003, 42, 4197
11. Cicchi, S.; Pescitelli, G.; Lascialfari, L.; Ghini, G.; di Bari, L.; Brandi, A.; Bussotti, L.; Atsbeha, T.; Marcelli, A.; Foggi, P.; Berti, D.; Mannini, M. Chirality 2011, 23, 833
12. Tiller, J. C. Angew. Chem., Int. Ed. 2003, 42, 3072
13. Abdallah, D. J.; Weiss, R. G. Adv. Mater. 2000, 12, 1237
14. Haering, G.; Luisi, P. L. J. Phys. Chem. 1986, 90, 5892
15. Karinaga, R.; Jeong, Y.; Shinkai, S.; Kaneko, K.; Sakurai, K. Langmuir 2005, 21, 9398
16. Gao, P.; Zhan, C. L.; Liu, M. H. Langmuir 2006, 22, 775
17. Van Bommel, K. J. C.; Friggeri, A.; Shinkai, S. Angew. Chem., Int. Ed. 2003, 42, 980
18. Kim, S. S.; Zhang, C. P. Science 1998, 282, 1302
19. Jung, J. H.; Ono, Y.; Hanabusa, K.; Shinkai, S. J. Am. Chem. Soc. 2000, 122, 5008
20. Kiyonaka, S.; Sugiyasu, K.; Shinkai, S.; Hamachi, I. J. Am. Chem. Soc. 2002, 124, 10954
21. Kobayashi, A.; Hamasaki, N.; Suzuki, M.; Kimura, M.; Shirai, H.; Hanabusa, K. J. Am. Chem. Soc. 2002, 124, 6550
22. Jung, H. J.; Ono, Y.; Shinkai, S. Angew. Chem., Int. Ed. 2000, 39, 1862
23. Dawn, A.; Shiraki, T.; Haraguchi, S.; Tamaru, S.-I.; Shinkai, S. Chem. Asian J. 2011, 6, 266
24. Ono, Y.; Nakashima, K.; Sano, M.; Hojo, J.; Shinkai, S. J. Mater. Chem. 2001, 11, 2419
25. Photoresponsive organogel based on azobenzene: Zhou, Y.; Xu, M.; Wu, J.; Yi, T.; Han, J.; Xiao, S.; Li, F.; Huang, C. J. Phys. Org. Chem. 2008, 21, 338
26. Chen, D.; Liu, H.; Kobayashi, T.; Yu, H. J. Mater. Chem. 2010, 20, 3610
27. Lucas, L. N.; Esch, J.; Kellogg, R. M.; Feringa, B. L. Chem. Commun. 2001, 759
28. Stimuli-responsive gels: Yang, X.; Zhanga, G.; Zhang, D. J. Mater. Chem. 2012, 22, 38
29. Cholesterol-based azobenzene switch: Murata, K.; Aoki, M.; Suzuki, T.; Harada, T.; Kawabata, H.; Komori, T.; Ohseto, F.; Keiko, K.; Shinkai, S. J. Am. Chem. Soc. 1994, 116, 6664
30. Ajayaghosh, A.; Varghese, R.; George, S. J.; Vijayakumar, C. Angew. Chem., Int. Ed. 2006, 45, 1141
31. Ajayaghosh, A.; Praveen, V. K. Acc. Chem. Res. 2007, 40, 644
32. de Jong, J. J. D.; Lucas, L. N.; Kellogg, R. M.; van Esch, J. H.; Feringa, B. L. Science 2004, 304, 278
33. Azobenzene-based chiral bis(urea) switch: de Loos, M.; van Esch, J.; Kellogg, R. M.; Feringa, B. L. Angew. Chem., Int. Ed. 2001, 40, 613
34. Pijper, D.; Jongejan, M. G. M.; Meetsma, A.; Feringa, B. L. J. Am. Chem. Soc. 2008, 130, 4541
35. Pijper, D.; Feringa, B. L. Soft Matter 2008, 4, 1349
36. Chen, C. T.; Chou, Y. C. J. Am. Chem. Soc. 2000, 122, 7662
37. Chen, C. T.; Chen, W. C.; Lee, Y. W. Org. Lett. 2010, 12, 1472
38. Chen, W. C.; Lin, P. C.; Chen, C. H.; Chen, C. T. Chem.-Eur. J. 2010, 16, 12822
39. Mukhopadhyay, P.; Iwashita, Y.; Shirakawa, M.; Kawano, S. I.; Fujita, N.; Shinkai, S. Angew. Chem., Int. Ed. 2006, 45, 1592
40. Hafkamp, R. J. H.; Kokke, B. P. A.; Danke, I. M.; Geurts, M. P. H.; Rowan, A. E.; Feiters, M. C.; Nolte, R. J. M. Chem. Commun. 1997, 545
41. Helmich, F.; Lee, C. C.; Schenning, A. P. H. J.; Meijer, E. W. J. Am. Chem. Soc. 2010, 132, 16753
42. Beginn, U.; Zipp, G.; Mourran, A.; Walther, P.; Möller, M. Adv. Mater. 2000, 12, 513
43. Review of dynamic helical structures: Maeda, K.; Yashima, E. Top. Curr. Chem. 2006, 265, 47
44. Pratihar, P.; Ghosh, S.; Stepanenko, V.; Patwardhan, S.; Grozema, F. C.; Siebbeles, L. D. A.; Würthner, F. Beilstein J. Org. Chem. 2010, 6, 1070
45. Kaiser, T. E.; Stepanenko, V.; Würthner, F. J. Am. Chem. Soc. 2009, 131, 6719
46. Würthner, F.; Bauer, C.; Stepanenko, V.; Yagai, S. Adv. Mater. 2008, 20, 1695
47. Li, X.-Q.; Zhang, X.; Ghosh, S.; Würthner, F. Chem.-Eur. J. 2008, 14, 8074
48. Stilbene as a photoresponsive unit in organogels: Miljanić, S.; Frkanec, L.; Meić, Z.; Žinić, M. Eur. J. Org. Chem. 2006, 1323
49. Engelkamp, H.; Middelbeek, S.; Nolte, R. J. M. Science 1999, 284, 785
50. See the Supporting Information for the synthesis of 1 and the X-ray crystal structure of its precursor (10 R,11 R, M)- 11 (Figure S1).