Synthesis, optical, and electrochemical properties of a new family of dendritic oligothiophenes

Journal of Organic Chemistry

Volumn 71, Issue 25, 2006, Pages 9475-9483

  Zhang, Yong ^b   Zhao, Chunchang ^a   Yang, Jinhua ^a   Kapiamba, Mbiya ^a   Haze, Olesya ^a   Rothberg, Lewis J ^a,b   Ng, Man Kit ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

^b University of Rochester   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AGGLOMERATION; CATALYSIS; ELECTROCHEMISTRY; ESTERIFICATION; OPTICAL PROPERTIES; PALLADIUM; SPECTROSCOPIC ANALYSIS;

CROSS-COUPLING REACTIONS; OLIGOTHIOPHENES; SOLVATOCHROMISM; THERMOCHROMISM;

DENDRIMERS;

CYANAMIDE; DENDRIMER; OLIGOTHIOPHENE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; ELECTROCHEMICAL ANALYSIS; ESTERIFICATION; SYNTHESIS; TEMPERATURE DEPENDENCE;

ELECTROCHEMISTRY; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; THIOPHENES;

EID: 33845531847     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0619581     Document Type: Article

References (53)

1. (a) Fréchet, J. M. J. Science 1994, 263, 1710-1715.
2. (b) Jansen, J. F. G. A.; de Brabander-van, den Berg, E. M. M.; Meijer, E. W. Science 1994, 266, 1226-1229.
3. (c) Newkome, G. R.; Moorefield, C. N.; Vögtle, F. Dendritic Molecules: Concepts, Syntheses, Perspectives; Wiley: Weinheim, 1996.
4. (d) Zeng, F.; Zimmerman, S. C. Chem. Rev. 1997, 97, 1681-1712.
5. (e) Fréchet, J. M. J. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 3713-3725.
6. (f) Pyun, J.; Zhou, X.-Z.; Drockenmuller, E.; Hawker, C. J. J. Mater. Chem. 2003, 13, 2653-2660.
7. (a) Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 1990, 112, 7638-7647.
8. (b) Nummelin, S.; Skrifvars, M.; Rissanen, K. Top. Curr. Chem. 2000, 210, 1-65.
9. (c) Gilat, S. L.; Adronov, A.; Fréchet, J. M. J. Angew. Chem., Int. Ed. 1999, 38, 1422-1427.
10. (d) Ihre, H.; Padilla, De Jesús, O. L.; Fréchet, J. M. J. J. Am. Chem. Soc. 2001, 123, 5908-5917.
11. (e) Morgan, M. T.; Carnahan, M. A.; Immoos, C. E.; Ribeiro, A. A.; Finkelstein, S.; Lee, S. J.; Grinstaff, M. W. J. Am. Chem. Soc. 2003, 125, 15485-15489.
12. (a) Reetz, M. T.; Giebel, D. Angew. Chem., Int. Ed. 2000, 39, 2498-2501.
13. (b) Boas, U.; Heegaard, P. M. H. Chem. Soc. Rev. 2004, 33, 43-63.
14. (c) Ballauff, M.; Likos, C. N. Angew. Chem., Int. Ed. 2004, 43, 2998-3020.
15. (a) Devadoss, C.; Bharathi, P.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 9635-9644.
16. (b) Moore, J. S. Acc. Chem. Res. 1997, 30, 402-413.
17. (c) Grayson, S. M.; Fréchet, J. M. J. Chem. Rev. 2001, 101, 3819-3868.
18. (d) Peng, Z.; Pan, Y.; Xu, B.; Zhang, J. J. Am. Chem. Soc. 2000, 122, 6619-6623.
19. (e) Berresheim, A. J.; Muller, M.; Mullen, K. Chem. Rev. 1999, 99, 1747-1786.
20. Fichou, D., Ed. Handbook of Oligo- and Polythiophenes; Wiley: Weinheim. 1999.
21. (a) Inganaes, O.; Berggren, M.; Andersson, M. R.; Gustafsson, G.; Hjertberg, T.; Wennerstroem, O.; Dyreklev, P.; Granstroem, M. Synth. Met. 1995, 71, 2121-2124.
22. (b) Pei, J.; Yu, W.; Huang, W.; Heeger, A. J. Macromolecules 2000, 33, 2462-2471.
23. (c) Mazzeo, M.; Vitale, V.; Della Sala, F.; Pisignano, D.; Anni, M.; Barbarella, G.; Favaretto, L.; Zanelli, A.; Cingolani, R.; Gigli, G. Adv. Mater. 2003, 15, 2060-2063.
24. (a) Koezuka, H.; Tsumura, A.; Ando, T. Synth. Met. 1987, 18, 699-704.
25. (b) Katz, H. E.; Bao, Z.; Gilat, S. L. Acc. Chem. Res. 2001, 34, 359-369.
26. (c) Salleo, A.; Chen, T. W.; Völkel, A. R.; Wu, Y.; Liu, P.; Ong, B. S.; Street, R. A. Phys. Rev. B 2004, 70, 115311.
27. (a) Huynh, W. U.; Dittmer, J. J.; Alivisatos, A. P. Science 2002, 295, 2425-2427.
28. (b) Padinger, F.; Rittberger, R. S.; Sariciftci, N. S. Adv. Funct. Mater. 2003, 13, 85-88.
29. (c) Coakely, K. M.; Liu, Y.; McGehee, M. D.; Frindell, K. M.; Stucky, G. D. Adv. Funct. Mater. 2003, 13, 301-306.
30. Yu, G.; Phillips, S. D.; Tomozawa, H.; Heeger, A. J. Phys. Rev. B 1990, 42, 3004.
31. (a) Marsella, M. J.; Swager, T. M. J. Am. Chem. Soc. 1993, 115, 12214-12215.
32. (b) McCullough, R. D.; Williams, S. P. J. Am. Chem. Soc. 1993, 115, 11608-11609.
33. (c) Leclerc, M.; Ho, H. A. J. Am. Chem. Soc. 2004, 126, 1384-1387.
34. Leclerc, M.; Ho, H. A. Synlett 2004, 2, 380-387.
35. (a) Xia, C.; Fan, X.; Locklin, J.; Advincula, R. C. Org. Lett. 2002, 4, 2067-2070.
36. (b) Xia, C.; Fan, X.; Locklin, J.; Advincula, R. C.; Gies, A.; Nonidez, W. J. Am. Chem. Soc. 2004, 126, 8735-8743.
37. For an interesting work on photochromic dendrimers containing an azobenzene linkage in the internal dendrimer structure that is capable of undergoing structural reorganization, see: Liao, L.-X.; Stellacci, F.; McGrath, D. V. J. Am. Chem. Soc. 2004, 126, 2181-2185.
38. (a) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1469.
39. (b) Ng, M.-K.; Wang, L.; Yu, L. Chem. Mater. 2000, 12, 2988-2995.
40. (c) Zhao, C.; Zhang, Y.; Wang, C.; Rothberg, L. J.; Ng, M.-K. Org. Lett. 2006, 8, 1585-1588.
41. (a) Lin, C.; Tour, J. J. Org. Chem. 2002, 67, 7761-7768.
42. (b) Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295-4298.
43. Messmore, B. W.; Hulvat, J. F.; Sone, E. D.; Stupp, S. I. J. Am. Chem. Soc. 2004, 126, 14452-14458.
44. (a) Chen, J.; Li, S.; Zhang, L.; Liu, B.; Han, Y.; Yang, G.; Li, Y. J. Am. Chem. Soc. 2005, 127, 2165-2171.
45. (b) Thomas, K. R. J.; Thompson, A. L.; Sivakumar, A. V.; Bardeen, C. J.; Thayumanavan, S. J. Am. Chem. Soc. 2005, 127, 373-383.
46. (a) Jakubiak, R.; Bao, Z.; Rothberg, L. J. Synth. Met. 2000, 114, 61.
47. (b) Tian, H.; Wang, J.; Shi, J.; Yan, D.; Wang, L.; Geng, Y.; Wang, F. J. Mater. Chem. 2005, 15, 3026-3033.
48. Likos, C. N.; Ballauff, M. Top. Curr. Chem. 2005, 245, 239-252.
49. (a) Lévesque, I.; Leclerc, M. Synth. Met. 1997, 84, 203-204.
50. (b) DiCésare, N.; Belletête, M.; Raymond, F.; Leclerc, M.; Durocher, G. J. Phys. Chem. A 1997, 101, 776-782.
51. (c) DiCésare, N.; Belletête, M.; Leclerc, M.; Durocher, G. Synth. Met. 1998, 98, 31-40.
52. (a) Collison, C. J.; Rothberg, L. J.; Treemaneekarn, V.; Li, Y. Macromolecules 2001, 34, 2346-2352.
53. (b) Schenning, A. P. H. J.; Kilbinger, A. F. M.; Biscarini, F.; Cavallini, M.; Cooper, H. J.; Derrick, P. J.; Feast, W. J.; Lazzaroni, R.; Leclère, Ph.; McDonell, L. A.; Meijer, E. W.; Meskers, S. C. J. J. Am. Chem. Soc. 2002, 124, 1269-1275.