Chirality-sensing binaphthocrown ether-polythiophene conjugate

Chemistry - A European Journal

Volumn 16, Issue 26, 2010, Pages 7859-7864

  Fukuhara, Gaku ^a   Inoue, Yoshihisa ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Amino acids; Chirality; Crown ethers; Polymers; Polythiophene

Indexed keywords

BACKBONE STRUCTURES; BINAPHTHYL UNITS; BITHIOPHENES; CHIRAL CROWN ETHERS; CIRCULAR DICHROISM; EFFECTIVE CONJUGATION LENGTH; ENHANCED SENSITIVITY; METHYL ESTERS; OPTICAL SIGNALS; OXYETHYLENE; POLY-THIOPHENE;

AMINO ACIDS; CHIRALITY; CROWN ETHERS; DICHROISM; DYES; ENANTIOMERS; ENANTIOSELECTIVITY; ESTERS; LIGANDS; ORGANIC ACIDS; POLYMERS; STEREOCHEMISTRY; THIOPHENE;

ETHERS;

AMINO ACID; CROWN ETHER; ETHER DERIVATIVE; POLYMER; POLYTHIOPHENE; THIOPHENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

AMINO ACIDS; CIRCULAR DICHROISM; CROWN ETHERS; ETHERS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; POLYMERS; STEREOISOMERISM; THIOPHENES;

EID: 77954317438     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200903545     Document Type: Article

References (58)

1. For recent reviews, see; a) K. S. Johnson, J. A. Needoba, S. C. Riser, W.J. Showers, Chem. Rev. 2007,107, 623-640;
2. b) B. Pejcic, P. Eadington, A. Ross, Environ. Sci. Technol. 2007, 41, 6333-6342.
3. For recent examples, see; a) E. S. Snow, F. K. Perkins, E. J. Houser, S. C. Badescu, T. L. Reinecke, Science 2005,307, 1942-1945;
4. b) S. J. Toal, W. C. Trogler, J. Mater. Chem. 2006,16, 2871-2883;
5. c)R. Bernini, M. Tonezzer, F. Mottola, L. Zeni, A. Quaranta, G. Maggioni, S. Carturan, G. Della Mea, Sens. Actuators B 2007,127, 231-236;
6. d)F. Wang, H. Gu, TM. Swager, J. Am. Chem. Soc. 2008, 130, 53925393.
7. For recent reviews, see; a) D. J. Hill, M. J. Mio, R. B. Prince, T.S. Hughes, J.S. Moore, Chem. Rev. 2001, 101, 3893-4011;
8. b)T. Nakano, Y Okamoto, Chem. Rev. 2001, 101, 4013-4038;
9. c)J.-M, Lehn, Prog. Polym. Sci. 2005, 30, 814-831;
10. d)F. J. M. Hoeben, P. Jonkheijm, E. W. Meijer, A. P. H. J. Schenning, Chem. Rev. 2005, 105, 1491.-1546;
11. e) K. Sada, M. Takeuchi, N. Fujita, M. Numata, S. Shinkai, Chem. Soc. Rev. 2007,36,415-435.
12. a) U. H. F. Bunz, Chem. Rev. 2000, 100, 1605-1644;
13. b)D.T. MeQuade, A. E. Pullen, T. M. Swager, Chem. Rev. 2000,100, 2537-2574;
14. c)S. W. Thomas III, G. D. Joly, T.M. Swager, Chem. Rev. 2007,107,1339-1386.
15. For reviews, see; a) D. J. Cram, J.M. Cram, Acc. Chem. Res. 1978, 11, 8-14;
16. b) D. J. Cram, Science 1988, 240, 760-767;
17. c)L. Pu, Acta Polym. 1997, 48, 116-141;
18. d)L. Pu, Chem. Rev. 1998, 98, 24052494;
19. e)L. Pu, Macromol. Rapid Commun. 2000, 21, 795-809;
20. f) M. M. Green, K.-S. Cheon, S.-Y. Yang, J.-W. Park, S. Swansburg, W. Liu, Acc. Chem. Res. 2001, 34, 672-680;
21. g) J. J. L. M. Cornelissen, A. E. Rowan, R. J. M. Nolte, N. A. J. M. Sommerdijk, Chem. Rev. 2001, 101, 4039-4070;
22. h) M. A. Mateos-Timoneda, M. CregoCalama, D. N. Reinhoudt, Chem. Soc. Rev. 2004, 33, 363-372;
23. i)L. Pu, Chem. Rev. 2004, 104, 1687-1716;
24. j) E. Yashima, K. Maeda, T. Nishimura, Chem. Eur. J. 2004,10, 42-51;
25. k) K. Maeda, E. Yashima, Top. Curr. Chem. 2006, 265, 47-88;
26. A. R. A. Palmans, E. W. Meijer, Angew. Chem. 2007,119, 9106-9126;
27. Angew. Chem. Int Ed. 2007, 46, 8948-8968;
28. l)G. A. Hembury, V. V. Borovkov, Y. Inoue, Chem. Rev. 2008, 108, 1-73.
29. a) G. Fukuhara, S. Madenci, J. Polkowska, F. Bastkowski, F.-G. Klärner, Y. Origane, M. Kaneda, T Mori, T Wada, Y. Inoue, Chem. Eur. J. 2007,13, 2473-2479;
30. b) G. Fukuhara, F.-G. Klärner, T Mori, T. Wada, Y. Inoue, Photochem. Photobiol. Sci. 2008, 7, 1493-1500, and other chiral molecular sensors are cited in this reference.
31. a)M.J. Marsella, T.M. Swager, J. Am. Chem. Soc. 1993, 115, 12214-12215;
32. b) M.J. Marsella, P.J. Carroll, T.M. Swager, J. Am. Chem. Soc. 1994,116, 9347-9348.
33. a) G. Manecke, H.-J. Winter, Makromol. Chem. Rapid Commun. 1981, 2, 569-571;
34. b)T. Kakuchi, K. Yokota, Makromol. Chem. Rapid Commun. 1985, 6, 551-555;
35. c)T. Kakuchi, K. Aoki, O. Haba, K. Yokota, Polym Bull. 1993, 31, 37-42;
36. d)H. Cheng, L. Ma, Q.-S. Hu, X.-F. Zheng, X Anderson, L. Pu, Tetrahedron: Asymmetry 1996, 7, 3083-3086;
37. e)H.M. Janssen, E. Peelers, M. F. van Zundert, M. H. P. van Genderen, E. W. Meijer, Macromolecules 1997, 30, 8113-8128;
38. f) T. Koide, K. Ueno, J. Chromatogr. A 2001, 909, 305315;
39. g) E. Yashima, Anal. Sci. 2002, 18, 3-6;
40. h) R. Nonokawa, E. Yashima, J. Am. Chem. Soc. 2003, 125, 1278-1283;
41. i)R. Nonokawa, E. Yashima, J. Polym. Sci. Polym. Chem. Ed. 2003, 41, 1004-1013;
42. j) R. Sakai, T. Satoh, R. Kakuchi, H. Kaga, T. Kakuchi, Macromolecules 2003, 36, 3709-3713;
43. k) R. Nonokawa, M. Oobo, E. Yashima, Macromolecules 2003, 36, 6599-6606;
44. l)K. Morino, M. Oobo, E. Yashima, Macromolecules 2005, 38, 3461-3468;
45. m)R. Sakai, I. Otsuka, T. Satoh, R. Kakuchi, H. Kaga, T. Kakuchi, Macromolecules 2006,39, 4032-4037;
46. n) T. Miyagawa, M. Yamamoto, R. Muraki, H. Onouchi, E. Yashima, J. Am. Chem. Soc. 2007, 129, 3676-3682;
47. o) H. Huang, Q. Miao, Y Rang, X. Huang, J. Xu, Y Cheng, Bull. Chem. Soc. Jpn. 2008, 81, 1116-1124.
48. N. T. Greene, K. D. Shimizu, J. Am. Chem, Soc. 2005, 127, 56955700.
49. E. Yashima, K. Maeda, O. Sato, J. Am. Chem. Soc. 2001,123, 81598160.
50. The detailed synthetic procedures and characterizations of the obtained (poly)thiophenes were given in the Supporting Information (Figures S1-S9).
51. a) S. F. Mason, R. H. Seal, Tetrahedron 1974, 30, 1671-1682;
52. b) L. D. Bari, G. Pescitelli, P. Salvadori, J. Am. Chem. Soc. 1999, 127, 7998-8004.
53. Since the UV spectral changes of the monomer upon addition of the guest were small, the g factor profiles obtained from the CD changes were used in the titration experiment.
54. Although this UV spectral, change was relatively small, due to the flexible linkage to the bithiophene monomer units, we can measure the change as a significant signal, gain with small errors (<8.5%).
55. The titration data and the curve fittings for all the examined cases were given in the Supporting Information (Figures S10-S19).
56. a) H. Tsukube, J. Chem. Soc. Chem, Commun. 1983, 970-971;
57. b) K. Hirose, A. Fujiwara, K. Matsunaga, N. Aoki, Y Tobe, Tetrahedron: Asymmetry 2003, 14, 555-566;
58. c)A. E. Lovely, T.J. Wenzel, Org. Lett. 2006, 8, 2823-2826.