Double helices with a controlled helicity composed of biphenol-derived phosphoric acid diesters

Chemistry - A European Journal

Volumn 15, Issue 28, 2009, Pages 6794-6798

  Yamada, Hidekazu ^a   Maeda, Katsuhiro ^a,b   Yashima, Eiji ^a  

^a NAGOYA UNIVERSITY   (Japan)

^b KANAZAWA UNIVERSITY   (Japan)

Author keywords

Chiral amplification; Chirality; Helical structures; Self assembly; Supramolecular chemistry

Indexed keywords

AROMATIC RINGS; BIPHENOL; BIPHENYL DERIVATIVES; CARBOXYLATE SALTS; CHIRAL AMPLIFICATION; DIESTERS; DOUBLE HELIX; DOUBLE-HELICAL; HELICAL SENSE; HELICAL STRUCTURES; HELICITY; INDUCED CIRCULAR DICHROISM; MODULAR STRATEGY; OPTICALLY ACTIVE; PHOSPHORYL CHLORIDE;

ACIDS; AROMATIC COMPOUNDS; CARBOXYLATION; CHIRALITY; CHLORINE COMPOUNDS; CHROMOPHORES; DICHROISM; ENANTIOMERS; MACROMOLECULES; OLIGOMERS; PHOSPHORIC ACID; SELF ASSEMBLY; STEREOCHEMISTRY; SUPRAMOLECULAR CHEMISTRY;

AMPLIFICATION;

ESTER; PHENOL DERIVATIVE; PHOSPHORIC ACID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

ESTERS; MODELS, MOLECULAR; PHENOLS; PHOSPHORIC ACIDS;

EID: 67650446865     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901075     Document Type: Article

References (46)

1. J. D. Watson, F. C Crick, Nature 1953,171, 737-738.
2. For reviews and selected examples of artificial double helices including helicates, see: a)J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995
3. b) C Piguet, G. Bernardinelli, G. Hopfgartner, Chem. Rev. 1997, 97, 2005-2062
4. c) M. Albrecht, Chem. Rev. 2001, 101, 3457-3497
5. d) V. Berl, I. Hue, R. G. Khoury, M.J. Krische, J.M. Lehn, Nature 2000, 407, 720-723
6. e) V. Berl, I. Hue, R. G. Khoury, J.-M. Lehn, Chem. Eur. J. 2001, 7, 2810-2820
7. f) I. Hue, Eur. J. Org. Chem. 2004, 17-29.
8. a) Y Tanaka, H. Katagiri, Y Furusho, E. Yashima, Angew. Chem. 2005, 117, 3935-3938;
9. Angew. Chem. Int. Ed. 2005, 44, 3867-3870
10. b) M. Ikeda, Y Tanaka, T. Hasegawa, Y Furusho, E. Yashima, J. Am. Chem. Soc. 2006,128, 6806-6807
11. c) Y Furusho, Y Tanaka, E. Yashima, Org. Lett. 2006, 8, 2583-2586
12. d) Y Furusho, E. Yashima, Chem. Rec. 2007, 7, 1-11
13. e)T. Hasegawa, Y Furusho, H. Katagiri, E. Yashima, Angew. Chem. 2007, 119, 5989-5992;
14. Angew. Chem. Int. Ed. 2007, 46, 5885-5888
15. f)T. Maeda, Y Furusho, S.-I. Sakurai, J. Kumaki, K. Okoshi, E. Yashima, J. Am. Chem. Soc. 2008, 130, 7938-7945.
16. a) H. Sugiura, Y Nigorikawa, Y Saiki, K. Nakamura, M. Yamaguchi, J Am. Chem. Soc. 2004,126, 14858-14864
17. b) H. Goto, H. Katagiri, Y Furusho, E. Yashima, J. Am. Chem. Soc. 2006, 128, 7176-7178.
18. For reviews on artificial single helical oligomers and polymers, see a) M. M. Green, J.-W. Park, T. Sato, A. Teramoto, S. Lifson, R. L. B. Selinger, J. V. Selinger, Angew. Chem. 1999, 111, 3328-3345;
19. Angew. Chem. Int. Ed. 1999, 38, 3138-3154
20. b)D.J. Hill, M.J. Mio, R.B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 2001, 101, 3893-4011
21. c)T. Nakano, Y Okamoto, Chem. Rev. 2001, 101, 4013-4038
22. d)J.J. L. M. Cornelissen, A. E. Rowan, R. J. M. Nolte, N. A.J. M. Sommerdijk, Chem. Rev. 2001, 101, 4039-4070
23. e) L. Brunsveld, B.J. B. Folmer, E. W. Meijer, R. P. Sijbesma, Chem. Rev. 2001, 101, 4071-4097
24. f) M. Fujiki, Macromol. Rapid Commun. 2001, 22, 539-563
25. g) E. Yashima, K. Maeda, T. Nishimura, Chem. Eur. J. 2004,10, 42-51
26. h)E. Yashima, K. Maeda, Macromolecules 2008, 41, 3-12.
27. a) J. Sánchez-Quesada, C. Steel, P. Prados, J. de Mendoza, J. Am. Chem. Soc. 1996, 118, 277-278
28. b) A. P. Bisson, C.A. Hunter, Chem. Commun. 1996, 1723-1724
29. c) J. L. Sessler, R. Wang, J. Am. Chem. Soc. 1996, 118, 9808-9809
30. d) B. Gong, Y. Yan, H. Zeng, E. Skrzypczak-Jankunn, Y. W. Kim, J. Zhu, H. Ickes, J. Am. Chem. Soc. 1999, 121, 5607-5608
31. e)B.J.B. Folmer, R. P. Sijbesma, H. Koojiman, A. L. Spek, E. W. Meijer, J. Am. Chem. Soc. 1999, 121, 9001 -9007
32. f) P. S. Corbin, S. C Zimmerman, J. Am. Chem. Soc. 2000,122, 3779-3780
33. g) E. A. Archer, N.T. Goldberg, V. Lynch, M. J. Krische, J. Am. Chem. Soc. 2000, 122, 5006-5007
34. h) J. S. Nowick, D. M. Chung, K. Maitra, S. Maitra, K. D. Stigers, Y. Sun, J. Am. Chem. Soc. 2000, 122, 7654-7661
35. i) G. Schmuck, W. Wienand, J. Am. Chem. Soc. 2003, 125, 452-459
36. j)T. Moriuchi, T. Tamura, T. Hirao, J. Am. Chem. Soc. 2004,126, 9356-9357.
37. M. Hojo, H. Hasegawa, Z. Chen, Bull. Chem. Soc. Jpn. 1996, 69, 2215-2220.
38. a) T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592-1594;
39. Angew. Chem. Int. Ed. 2004, 43, 1566-1568
40. b) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356-5357.
41. See the Supporting Information for details of the synthesis, structures, and characterization of compounds.
42. R. Fiesel, U. Scherf, Acta Polym. 1998, 49, 445-449.
43. 2, an intense split-type ICD was also observed at around 250 nm probably due to the absorption of the biphenol moieties. However, the addition of ethanol resulted in the disappearance of the ICD in the absorption region of the biphenol moieties as well as the π-conjugated chromophore region (see Figure S2 in the Supporting Information). These results indicate that a preferred-handed axially twisted conformation was also induced in the biphenol moieties upon the formation of a homo-double helix with an excess handedness.
44. 1H NMR spectra of (S)-I as a function of the temperature; that is, formation of a small aggregate for (S)-I rather than a specific duplex at high temperature, and this possibility could not be completely excluded, although the MS data support the duplex formation.
45. 2, although their absorption and NMR spectral patterns differ.
46. 6 (see Figure S24 in the Supporting Information). 6799-6801