Reaction of 4H-cyclopenta[2,1-b:3,4-b′]dithiophenes with NBS - A route toward 2H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-diones

Tetrahedron

Volumn 69, Issue 10, 2013, Pages 2260-2267

  Marin, Lidia ^a   Van Mierloo, Sarah ^a   Zhang, Yuexing ^b   Robeyns, Koen ^c   Champagne, Benoît ^b   Adriaensens, Peter ^a   Lutsen, Laurence ^a   Vanderzande, Dirk ^a   Maes, Wouter ^a  

^a HASSELT UNIVERSITY   (Belgium)

^b UNIVERSITY OF NAMUR   (Belgium)

^c UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

2H Cyclopenta 2,1 b:3,4 b dithiophene 2,6(4H) dione; 4H Cyclopenta 2,1 b:3,4 b dithiophene (CPDT); Bromination; Gibbs free energy calculations; Solvent effects

Indexed keywords

2,6(4H) DIONE 2H CYCLOPENTA[2,1 B:3,4 B']DITHIOPHENE 2,6(4H) DIONE DERATIVE; 4H CYCLOPENTA[2,1 B:3,4 B']DITHIOPHENE DERIVATIVE; CYCLOPENTADITHIOPHENE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CRYSTAL STRUCTURE; ENERGY; PRIORITY JOURNAL; REACTION TIME; X RAY CRYSTALLOGRAPHY;

EID: 84873414089     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.01.026     Document Type: Article

References (72)

1. S. Günes, H. Neugebauer, and N.S. Sariciftci Chem. Rev. 107 2007 1324 1338
2. J. Nelson Mater. Today 14 2011 462 470
3. R. Søndergaard, M. Hösel, D. Angmo, T.T. Larsen-Olsen, and F.C. Krebs Mater. Today 15 2012 36 49
4. P. Kumar, and S. Chand Prog. Photovoltaics 20 2012 377 415
5. G. Li, R. Zhu, and Y. Yang Nat. Photonics 6 2012 153 161
6. M. Jørgensen, K. Norrman, S.A. Gevorgyan, T. Tromholt, B. Andreasen, and F.C. Krebs Adv. Mater. 24 2012 580 612
7. L.J.A. Koster, S.E. Shaheen, and J.C. Hummelen Adv. Energy Mater. 2 2012 1246 1253
8. N. Espinosa, M. Hosel, D. Angmo, and F.C. Krebs Energy Environ. Sci. 5 2012 5117 5132
9. E. Bundgaard, and F.C. Krebs Sol. Energy Mater. Sol. Cells 91 2007 954 985
10. R. Po, M. Maggini, and N. Camaioni J. Phys. Chem. C 114 2009 695 706
11. C.J. Brabec, S. Gowrisanker, J.J.M. Halls, D. Laird, S. Jia, and S.P. Williams Adv. Mater. 22 2010 3839 3856
12. P.-L.T. Boudreault, A. Najari, and M. Leclerc Chem. Mater. 23 2010 456 469
13. A.J. Heeger Chem. Soc. Rev. 39 2010 2354 2371
14. J.L. Delgado, P.-A. Bouit, S. Filippone, M.A. Herranz, and N. Martin Chem. Commun. 2010 4853 4865
15. B. Thompson, P. Khlyabich, B. Burkhart, A. Aviles, A. Rudenko, G. Shultz, F. Christi, and L. Mangubat Green 1 2011 29 54
16. A. Mishra, and P. Bäuerle Angew. Chem., Int. Ed. 51 2012 2020 2067
17. H. Zhou, L. Yang, and W. You Macromolecules 45 2012 607 632
18. R.L. Uy, S.C. Price, and W. You Macromol. Rapid Commun. 33 2012 1162 1177
19. L. Bian, E. Zhu, J. Tang, W. Tang, and F. Zhang Prog. Polym. Sci. 37 2012 1292 1331
20. Y. Liang, and L. Yu Acc. Chem. Res. 43 2010 1227 1236
21. S. Hellstrom, L.J. Lindgren, Y. Zhou, F. Zhang, O. Inganas, and M.R. Andersson Polym. Chem. 1 2010 1272 1280
22. H. Bronstein, Z. Chen, R.S. Ashraf, W. Zhang, J. Du, J.R. Durrant, P. Shakya Tuladhar, K. Song, S.E. Watkins, Y. Geerts, M.M. Wienk, R.A.J. Janssen, T. Anthopoulos, H. Sirringhaus, M. Heeney, and I. McCulloch J. Am. Chem. Soc. 133 2011 3272 3275
23. J. Sun, Y. Zhu, X. Xu, L. Lan, L. Zhang, P. Cai, J. Chen, J. Peng, and Y. Cao J. Phys. Chem. C 116 2012 14188 14198
24. D. Mühlbacher, M. Scharber, M. Morana, Z. Zhu, D. Waller, R. Gaudiana, and C. Brabec Adv. Mater. 18 2006 2884 2889
25. J. Peet, J.Y. Kim, N.E. Coates, W.L. Ma, D. Moses, A.J. Heeger, and G.C. Bazan Nat. Mater. 6 2007 497 500
26. C. Soci, I.W. Hwang, D. Moses, Z. Zhu, D. Waller, R. Gaudiana, C.J. Brabec, and A.J. Heeger Adv. Funct. Mater. 17 2007 632 636
27. M. Lenes, M. Morana, C.J. Brabec, and P.W.M. Blom Adv. Funct. Mater. 19 2009 1106 1111
28. C.-H. Hsieh, Y.-J. Cheng, P.-J. Li, C.-H. Chen, M. Dubosc, R.-M. Liang, and C.-S. Hsu J. Am. Chem. Soc. 132 2010 4887 4893
29. P. Boland, K. Lee, and G. Namkoong Sol. Energy Mater. Sol. Cells 94 2010 915 920
30. A. Teichler, R. Eckardt, S. Hoeppener, C. Friebe, J. Perelaer, A. Senes, M. Morana, C.J. Brabec, and U.S. Schubert Adv. Energy Mater. 1 2011 105 114
31. K.F. Jeltsch, M. Schädel, J.-B. Bonekamp, P. Niyamakom, F. Rauscher, H.W.A. Lademann, I. Dumsch, S. Allard, U. Scherf, and K. Meerholz Adv. Funct. Mater. 22 2012 397 404
32. M. Horie, J. Kettle, C.-Y. Yu, L.A. Majewski, S.-W. Chang, J. Kirkpatrick, S.M. Tuladhar, J. Nelson, B.R. Saunders, and M.L. Turner J. Mater. Chem. 22 2012 381 389
33. P. Willot, L. De Cremer, and G. Koeckelberghs Macromol. Chem. Phys. 213 2012 1216 1224
34. A.D. Schlüter J. Polym. Sci., Part A: Polym. Chem. 39 2001 1533 1556
35. M. Zhang, H.N. Tsao, W. Pisula, C. Yang, A.K. Mishra, and K. Müllen J. Am. Chem. Soc. 129 2007 3472 3473
36. J. Murage, J.W. Eddy, J.R. Zimbalist, T.B. McIntyre, Z.R. Wagner, and F.E. Goodson Macromolecules 41 2008 7330 7338
37. J.C. Bijleveld, M. Shahid, J. Gilot, M.M. Wienk, and R.A.J. Janssen Adv. Funct. Mater. 19 2009 3262 3270
38. J. Kettle, M. Horie, L.A. Majewski, B.R. Saunders, S. Tuladhar, J. Nelson, and M.L. Turner Sol. Energy Mater. Sol. Cells 95 2011 2186 2193
39. S. Kowalski, S. Allard, and U. Scherf ACS Macro Lett. 1 2012 465 468
40. Y. Zhang, J. Zou, C.-C. Cheuh, H.-L. Yip, and A.K.Y. Jen Macromolecules 45 2012 5427 5435
41. K. Pilgram, M. Zupan, and R. Skiles J. Heterocycl. Chem. 7 1970 629 633
42. U. Asawapiron, and U. Scherf Macromol. Rapid Commun. 22 2001 746 749
43. P. Coppo, D.C. Cupertino, S.G. Yeates, and M.L. Turner Macromolecules 36 2003 2705 2711
44. S. Gronowitz, J.E. Skramstad, and B. Erikksson Arkiv för kemi 21 1963 335 341
45. S. Gronowitz, J.E. Skramstad, and B. Erikksson Arkiv för kemi 28 1967 99 107
46. H. Wynberg, and A. Kraak J. Org. Chem. 29 1964 2455 2457
47. A. Kraak, A.K. Wiersema, P. Jordens, and H. Wynberg Tetrahedron 24 1968 3381 3398
48. P. Lucas, N.E. Mehdi, H.A. Ho, D. Bélanger, and L. Breau Synthesis 2000 1253 1258
49. J.Z. Brzeziński, and J.R. Reynolds Synthesis 2002 1053 1056
50. S. Van Mierloo, P.J. Adriaensens, W. Maes, L. Lutsen, T.J. Cleij, E. Botek, B. Champagne, and D.J. Vanderzande J. Org. Chem. 75 2010 7202 7209
51. S. Van Mierloo, J. Kesters, A. Hadipour, M.-J. Spijkman, N. Van den Brande, J. D'Haen, G. Van Assche, D.M. de Leeuw, T. Aernouts, J. Manca, L. Lutsen, D. Vanderzande, and W. Maes Chem. Mater. 24 2012 587 593
52. L. Marin, Y. Zhang, K. Robeyns, B. Champagne, P. Adriaensens, L. Lutsen, D. Vanderzande, D. Bevk, and W. Maes Tetrahedron Lett. 54 2013 526 529
53. R.C. Coffin, J. Peet, J. Rogers, and G.C. Bazan Nat. Chem. 1 2009 657 661
54. H.H. Wasserman, and J.L. Ives Tetrahedron 37 1981 1825 1852
55. T. Caronna, M. Forte, M. Catellani, and S.V. Meille Chem. Mater. 9 1997 991 995
56. S. Gronowitz, and G.L. Borgen Acta Chem. Scand. 19 1965 1180 1184
57. L.T. Lin, and H. Hart J. Org. Chem. 47 1982 3570 3571
58. T. Agostinelli, M. Caironi, D. Natali, M. Sampietro, G. Dassa, E.V. Canesi, C. Bertarelli, G. Zerbi, J. Cabanillas-Gonzalez, S. De Silvestri, and G. Lanzani J. Appl. Phys. 104 2008 114508
59. S. Di Motta, F. Negri, D. Fazzi, C. Castiglioni, and E.V. Canesi J. Phys. Chem. Lett. 1 2010 3334 3339
60. M.-Y. Chang, and C.-H. Lin J. Chin. Chem. Soc. 58 2011 853 856
61. T. Chonan, and K. Takahashi Bull. Chem. Soc. Jpn. 77 2004 1487 1497
62. N. Cai, S.-J. Moon, L. Cevey-Ha, T. Moehl, R. Humphry-Baker, P. Wang, S.M. Zakeeruddin, and M. Grätzel Nano. Lett. 11 2011 1452 1456
63. D. Xu, S. Wang, Z. Shen, C. Xia, and W. Sun Org. Biomol. Chem. 10 2012 2730 2732
64. H. Diliën, L. Marin, E. Botek, B. Champagne, V. Lemaur, D. Beljonne, R. Lazzaroni, T.J. Cleij, W. Maes, L. Lutsen, D. Vanderzande, and P.J. Adriaensens J. Phys. Chem. B 115 2011 12040 12050
65. M. Frenklach, and D. Clary Ind. Eng. Chem. Fundam. 22 1983 433 436
66. E.J. Corey, and M. Ishiguro Tetrahedron Lett. 20 1979 2745 2748
67. D.R. Lide CRC Handbook of Chemistry and Physics: A Ready-reference of Chemical and Physical Data 85th ed. 2004 CRC LLC Boca Raton
68. H. Paulussen, B. Ottenbourgs, D. Vanderzande, P. Adriaensens, and J. Gelan Polymer 38 1997 5221 5225
69. C.A. Mills, D.M. Taylor, P.J. Murphy, C. Dalton, G.W. Jones, L.M. Hall, and A.V. Hughes Synth. Met. 102 1999 1000 1001
70. F.G. Brunetti, X. Gong, M. Tong, A.J. Heeger, and F. Wudl Angew. Chem., Int. Ed. 49 2010 532 536
71. Q. Wu, R. Li, W. Hong, H. Li, X. Gao, and D. Zhu Chem. Mater. 23 2011 3138 3140
72. M.J.T.G.W. Frisch, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N.J. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox Gaussian 09, Revision A.1 Wallingford CT 2009