Water-soluble, electroactive, and photoluminescent quaterthiophene- dinucleotide conjugates

Chemistry - A European Journal

Volumn 14, Issue 2, 2008, Pages 513-521

  Alesi, Silvia ^a   Brancolini, Giorgia ^a   Melucci, Manuela ^a   Capobianco, Massimo Luigi ^a   Venturini, Alessandro ^a   Camaioni, Nadia ^a   Barbarella, Giovanna ^a  

^a CNR   (Italy)

Author keywords

Charge mobility; Circular dichroism; Oligonucleotides; Photoluminescence; Thiophene

Indexed keywords

DICHROISM; IONIC STRENGTH; PHOTOLUMINESCENCE; THIOPHENE;

CHARGE MOBILITY; DINUCLEOTIDES; INTERMOLECULAR NUCLEOBASE; QUATERTHIOPHENE;

NUCLEOTIDES;

ADENOSINE; NUCLEOTIDE; THIOPHENE DERIVATIVE; THYMIDINE; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROCHEMISTRY; HYDROGEN BOND; LUMINESCENCE; METHODOLOGY; PHOTOCHEMISTRY; SOLUBILITY; STEREOISOMERISM; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

ADENOSINE; ELECTROCHEMISTRY; HYDROGEN BONDING; LUMINESCENCE; LUMINESCENT MEASUREMENTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NUCLEOTIDES; PHOTOCHEMISTRY; SOLUBILITY; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM; THIOPHENES; THYMIDINE; WATER;

EID: 38149030793     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700950     Document Type: Article

References (53)

1. a) A. R. Murphy, J. M. Fréchet, Chem. Rev. 2007, 107, 1066-1096;
2. b) M. H. Yoon, A. Facchetti, C. E. Stern, T. J. Marks, J. Am. Chem. Soc. 2006, 128, 5792-5801;
3. c) H. Sirringhaus, Adv. Mater. 2005, 17, 2411;
4. d) G. Barbarella, M. Melucci, G. Sotgiu, Adv. Mater. 2005, 17, 1581-1593.
5. a) H. A. Ho, M. Béra-Abérem, M. Leclerc, Chem. Eur. J. 2005, 11, 1718-1724;
6. b) A. Herland, P. Björk, K. P. R. Nillson, J. D. Olsson, P. Åsberg, P. Konradsson, P. Hammarström, O. Inganäs, Adv. Mater. 2005, 17, 1466-1471;
7. c) H. A. Ho, K. Dorè, M. Boissinot, M. G. Bergeron, R. M. Tanguay, D. Boudreau, M. Leclerc, J. Am. Chem. Soc. 2005, 127, 12673-12676;
8. d) K. Peter, R. Nilsson, O. Inganas, Nat. Mater. 2003, 2, 419-424.
9. a) B. Liu, G. C. Bazan, Chem. Mater 2004, 16, 4467-4476;
10. b) H. A. Ho, M. Boissinot, M. G. Bergeron, G. Corbeil, K. Doré, D. Boudreau, M. Leclerc, Angew. Chem. 2002, 114, 1618-1621;
11. Angew. Chem. Int. Ed. 2002, 41, 1548-1551,;
12. Angew. Chem. Int. Ed. 2002, 41, 1548-1551,.
13. a) F. E. Alemdaroglu, A. Herrmann, Org. Biomol. Chem., 2007, 5, 1311-1320;
14. b) K. Tanaka, M. Shionoya, Chem. Prod. Chem. Letters 2006, 35, 694-699;
15. c) F. D. Lewis, H. Zhu, P. Daublain, T. Fiebig, M. Raytchev, Q. Wang, V. Shafirovich, J. Am. Chem. Soc. 2006, 128, 791-800;
16. d) K. V. Gothelf, T. H. LaBean, Org. Biomol. Chem. 2005, 3, 4023-4037;
17. e) F. J. M. Hoeben, E. W. Meijer, A. P. H. J Schenning, Chem. Rev. 2005, 105, 1491-1546;
18. f) E. Katz, I. Willner, Angew. Chem. 2004, 116, 6166-6235;
19. Angew. Chem. Int. Ed. 2004, 43, 6042-6108,;
20. g) M. A. Abdalla, J. Bayer, J. O. Radler, K. Müllen, Angew. Chem. 2004, 116, 4057-4060;
21. Angew. Chem. Int. Ed. 2004, 43, 3967-3970,.
22. a) Y. Tang, F. He, M. Yu, F. Feng, L. An, H. Sun, S. Wang, Y. Li, D. Zhu, Macromol. Rapid Commun. 2006, 27, 389-392;
23. b) A. Ono, Macromol. Chem. Phys. 2006, 207, 1629-1632;
24. c) P. Bäuerle, A. Emge. Adv. Mater. 1998, 10, 324-330.
25. a) C. D. Dimitrakopoulos, P. R. L. Malenfant, Adv. Mater. 2002, 14, 99-117;
26. b) H. E. Katz, J. G. Laquindanum, A. Lovinger, J. Chemother, J. Chem. Mater. 1998, 10, 633-638;
27. c) R. S. Becker, J. Seixas de Melo, A. L. Maçanita, F. Elisei F. J. Phys. Chem. 1996, 100, 18683-18695;
28. d) D. Grebner, M. Helbig, S. Rentsch, J. Phys. Chem. 1995, 99, 16991-16998.
29. a) Y. Kanemitsu, K. Suzuki, Y. Masumoto, Phys. Rev. B 1994, 50, 2301-2305;
30. b) R. S. Becker, J. Seixas de Melo, A. L. Maçanita, F. Elisei, J. Phys. Chem. 1996, 100, 18683-18695;
31. c) M. Melucci, G. Barbarella, M. Zambianchi, P. Di Pietro, A. Bongini, J. Org. Chem. 2004, 69, 4821-4828;
32. d) M. Melucci, G. Barbarella, G. Sotgiu, J. Org. Chem. 2002, 67, 8877-8884.
33. a) D. G. Whitten, Acc. Chem. Res. 1993, 26, 502-509;
34. b) O. Henze, W. J. Feast, F. Gardebien, P. Jonkheijm, R. Lazzaroni, P. Leclère, E. W. Meijer, A. P. H. J. Schenning, J. Am. Chem. Soc. 2006, 128, 5923-5929;
35. c) F. Meinardi, M. Cerminara, S. Blumstengel, A. Sassella, A. Borghesi, R. Tubino, Phys. Rev. B 2003, 67, 184205-1-6;
36. d) M. Melucci, G. Barbarella, M. Gazzano, M. Cavallini, F. Biscarini, A. Bongini, F. Piccinelli, M. Monari, M. Bandini, A. Umani-Ronchi, P. Biscarini, Chem. Eur. J. 2006, 12, 7304-7312.
37. a) Circular Dicroism, (Eds.: N. Berova, K. Nakanishi, R. W. Woody), Wiley, New York, 2000;
38. b) Circular Dichroic Spectroscopy, (Eds.: N. Harada, K. Nakanishi), Oxford University Press, Oxford, 1983.
39. F. D. Lewis, L. Zhang, X. Liu, X. Zuo, D. M. Tiede, H. Long, G. C. Schaz, J. Am. Chem. Soc. 2005, 127, 14445-14453.
40. H. W. Jun, S. E. Paramonov, J. D. Hartgerin, Soft Matter 2006, 2, 177-181.
41. K. Ohdan, K. Fujii, M. Yanase, T. Takaha, T. Kuriki, Biocatal. Biotransform. 2006, 24, 77-81.
42. D. R. Lamb, Electrical Conduction Mechanisms in Thin Insulating Films, Methuen, London, 1967.
43. M. A. Lamport, P. Mark, Current Injection in Solids, Academic Press, New York, 1970.
44. P. Jonkheijm, N. Stutzmann, Z. Chen, D. M. de Leeuw, E. W. Meijer, A. P. H. J Schenning, A. P. H. J., F. Würthner, J. Am. Chem. Soc. 2006, 128, 9535-9540.
45. a) A. Acocella, A. Venturini, F. Zerbetto, J. Am. Chem. Soc. 2004, 126, 2362-2367;
46. b) J. Scott, P. A. Weiner, D. A.; Kollman, U. Case, J. Comput. Chem. 1990, 11, 440-467;
47. c) C. Singh, C. Ghio, G. Alagona, S. Profeta, P. Weiner, J. Am. Chem. Soc. 1984, 106, 765-784;
48. d) W. Clark Still, A. Tempczyk, R. C. Hawley, T. Hendrickson, J. Am. Chem. Soc. 1990, 112, 6127-6129.
49. Nucleic Acids. Structures, Properties and Functions (Eds.: V. A. Bloomfield, D. Crothers, I. Tinoco), University Science Books, Sausalito, CA, 2000.
50. F. D. Lewis, L. Zhang, X. Liu, X. Zuo, D. M. Tiede, H. Long, G. C. Schaz, J. Am. Chem. Soc. 2005, 127, 14445-14453.
51. M. Cirilli, F. Bachechi, G. Ughetto, F. P. Colonna, M. L. Capobianco, J. Mol. Biol. 1993, 230, 878-889.
52. J. E. Marugg, M. Tromp, P. Jhuran, C. F. Hoyng, G. A. van der Marel, J. H. van Boom, Tetrahedron 1984, 40, 73-78.
53. F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem. 1990, 11, 440-467.