Browse > Article
http://dx.doi.org/10.5012/jkcs.2016.60.1.21

Synthesis and Characterization of New Push-Pull Chromophores Containing BF2-Azopyrrole Derivatives  

Ko, HayeMin (Department of Bio-Nano Chemistry, Wonkwang University)
Publication Information
Abstract
Novel push-pull chromophores containing 5’-(4-(bis(9,9-dimethyl-9H-fluoren-2-yl)aniline (bisDMFA) as a donor and phenylazo-methylpyrrolyl-boron difluoride (PhAPy-BF2) as an acceptor were designed and synthesized by the Knoevenagel condensation reaction for organic solar cells. Various electron withdrawing moieties were effectively introduced using 2,4-dimethyl-1H-pyrrole to afford new asymmetric BF2-azopyrrole molecules that were characterized by UV-vis spectroscopy and cyclic voltammetry measurements.
Keywords
Organic solar cell; Asymmetric BF2-azopyrrole molecules;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Robertson, N. Angew. Chem. 2006, 118, 2398   DOI
2 Nielsen, T. D.; Cruickshank, C.; Foged, S.; Thorsen, J.; Krebs, F. C. Sol. Energy Mater. Sol. Cells. 2010, 94, 1553.   DOI
3 Krebs, F. C.; Norrman, K. ACS Appl. Mater. Interfaces.2010, 2, 877.
4 Mikroyannidis, J. A.; Kabanakis, A. N.; Tsagkournos, D. V.; Balraju, P.; Sharma, G. D. J. Mater. Chem. 2010, 20, 6464.   DOI
5 Chen, L. M.; Hong, Z. R.; Li, G.; Yang,Y. Adv. Mater. 2009, 21, 1434.   DOI
6 Domercq, B.; Grasso, C.; Maldonado, J. L.; Halik, M.; Barlow, S.; Marder, S. R.; Kippelen, B. J. Phys. Chem. B, 2004, 108, 8647.   DOI
7 Sun, Y.; Rohde, D.; Liu, Y.; Wan, L.; Wang, Y.; Wu, W.; Di, C.; Yu, G.; Zhu, D. J. Mater. Chem. 2006, 16, 4499.   DOI
8 Mikroyannidis, J. A.; Sharma, G. D.; Sharma, S. S.; Vijay,Y. K. J. Phys. Chem. C 2010, 114, 1520.   DOI
9 Mikroyannidisa,J. A.; Royd, M. S.; Sharma, G. D. J. Power Sources 2010,195, 5391.   DOI
10 Law, K. Y. Chem. Rev. 1993, 93, 449.   DOI
11 Ko, H. M.; Choi, H.; Paek, S.; Kim, K.; Song, K.; Lee, J. K.; Ko, J. J. Mater. Chem. 2011, 21, 7248.   DOI
12 Kim, S.; Lee, J. K.; Kang, S. O.; Ko, J.; Yum, J. H.; Fantacci, S.; Angelis, F. D.; Censo, D. D.; Nazeeruddin, M. D.; Gratzel, M. J. Am. Chem. Soc. 2006, 128, 16701.   DOI
13 Kim, S.; Choi, H.; Kim, D.; Song, K.; Kang, S. O.; Ko, J. Tetrahedron 2007, 63, 9206.   DOI
14 Rousseau, T.; Cravino, A.; Ripaud, E.; Leriche, P.; Rihn, S.; Nicola, A. D.; Ziesselb, R.; Roncali, J. Chem. Commun. 2010, 46, 5082.   DOI
15 Ziessel, R.; Ulrich, G.; Harriman, A.; Alamiry, M. A. H.; Stewart, B.; Retailleau, P. Chem. Eur. J. 2009, 15, 1359.   DOI
16 Blom, P. W. M.; de Jong, M. J. M.; van Munster, M. G. Phys. Rev. B 1997, 55, R656.   DOI
17 Blom, P. W. M.; Mihailetchi, V. D.; Koster, L. J. A.; Markov, D. E. Adv. Mater. 2007, 19, 1551.   DOI
18 Angew. Chem. Int. Ed. 2006, 45, 2338.   DOI
19 Krebs, F. C.; Tromholt, T.; Jørgensen, M. Nanoscale. 2010, 2, 873.   DOI
20 Bundgaard, E.; Hagemann, O.; Manceau, M.; Jørgensen, M.; Krebs, F. C.; Macromolecules 2010, 43, 8115.   DOI
21 Krebs, F. C.; Fyenbo, J.; Jørgensen, M. J. Mater. Chem. 2010, 20, 8994.   DOI
22 Walker, B.; Kim, C.; Nguyen, T.-Q. Chem. Mater. 2011, 23, 470.   DOI
23 Krebs, F. C.; Gevorgyan, S. A.; Alstrup, J. J. Mater. Chem. 2009, 19, 5442.   DOI
24 Lloyd, M. T.; Anthony, J. E.; Malliaras, G. G. Mater. Today 2007, 10, 34.
25 Kippelen, B.; Bredas, J.-L. Energy Environ. Sci. 2009, 2, 251.   DOI
26 Krebs, F. C.; Nielsen, T. D.; Fyenbo, J.; Wadstrøm, M.; Pedersen, M. S. Energy Environ. Sci. 2010, 3, 512.
27 Roncali, J. Acc. Chem. Res. 2009, 42, 1719.   DOI
28 Li, W.; Du, C.; Li, F.; Zhou, Y.; Fahlman, M.; Bo, Z.; Zhang, F. Chem. Mater. 2009, 21, 5327.   DOI
29 Lloyd, M. T.; Mayer, A. C.; Subramanian, S.; Mourey, D. A.; Herman, D. J.; Bapat, A. V.; Anthony, J. E.; Malliaras, G. G. J. Am. Chem. Soc. 2007, 129, 9144.   DOI
30 Marrocchi, A.; Silvestri, F.; Seri, M.; Facchetti, A.; Taticchi, A.; Marks, T. J. Chem. Commun. 2009, 45, 1380.
31 Bruckstummer, H.; Kronenberg, N. M.; Gsanger, M.; Stolte, M.; Meerholz, K.; Wurthner, F. J. Mater. Chem. 2010, 20, 240.   DOI
32 Kronenberg, N. M.; Deppisch, M.; Wurthner, F.; Lademann, H. W. A.; Deing, K.; Meerholz, K. Chem. Commun. 2008, 44, 6489.
33 Ma, C. Q.; Fonrodona, M.; Schikora, M. C.; Wienk, M. M.; Janssen, R. A. J.; Bauerle, P. Adv. Funct. Mater. 2008, 18, 3323.   DOI
34 Silvestri, F.; Irwin, M. D.; Beverina, L.; Facchetti, A.; Pagani, G. A.; Marks, T. J. J. Am. Chem. Soc. 2008, 130, 17640.   DOI
35 Mayerhoffer, U.; Deing, K.; Gruß, K.; Braunschweig, H.; Meerholz, K.; Wurthner, F. Angew. Chem. Int. Ed. 2009, 48, 8776.   DOI
36 Lincker, F.; Delbosc, N.; Bailly, S.; DeBettignies, R.; Billon, M.; Pron, A.; Demadrille, R. Adv. Funct. Mater. 2008, 18, 3444.   DOI
37 Liu, Y.; Wan, X.; Yin, B.; Zhou, J.; Long, G.; Yin, S.; Chen, Y. J. Mater. Chem. 2010, 20, 2464.   DOI
38 Velusamy, M.; Huang, J.-H.; Hsu, Y. C.; Chou, H. H.; Ho, K. C.; Wu, P. L.; Chang, W. H.; Lin, J.T.; Chu, C. W. Org. Lett. 2009, 11, 4898.   DOI
39 Xue, L. L.; He, J. T.; Gu, X.; Yang, Z. F.; Xu, B.;Tian, W. J. J. Phys. Chem. C 2009, 113, 12911.
40 Mikroyannidis, J. A.; Stylianakis, M. M.; Suresh, P.; Balraju, P.; Sharma, G. D. Org. Electron. 2009, 10, 1320.   DOI
41 Zhang, W.; Tse, S. C.; Lu, J.; Tao, Y.; Wong, M. S. J. Mater. Chem. 2010, 20, 2182.   DOI
42 Yang, Y.; Zhang, J.; Zhou, Y.; Zhao, G.; He, C.; Li, Y.; Andersson, M.; Inganas, O.; Zhang, F. J. Phys. Chem. C 2010, 114, 3701.   DOI
43 Zhao, X.; Piliego, C.; Kim, B. S.; Poulsen, D. A.; Ma, B.; Unruh, D. A.; Frechet, J. M. J. Chem. Mater. 2010, 22, 2325.   DOI
44 Tamayo, A. B.; Walker, B.; Nguyen, T. Q. J. Phys. Chem. C 2008, 112, 11545.   DOI
45 Tamayo, A. B.; Dang, X. D.; Walker, B.; Seo, J.; Kent, T.; Nguyen, T. Q. Appl. Phys. Lett. 2009, 94, 103301.   DOI
46 Walker, B.; Tamayo, A. B.; Dang, X. D.; Zalar, P.; Seo, J. H.; Garcia, A.; Tantiwiwat, M.; Nguyen, T. Q. Adv. Funct. Mater. 2009, 19, 3063.   DOI
47 Rousseau, T.; Cravino, A.; Bura, T.; Ulrich, G.; Ziessel, R.; Roncali, J. Chem. Commun. 2009, 45, 1673.
48 Benstead, M.; Mehl, G. H.; Boyle, R. W. Tetrahedron 2011, 67, 3573.   DOI
49 Kim, B.; Ma, B.; Donuru, V. R.; Liuc, H.; Frechet, J. M. J. Chem. Commun. 2010, 46, 4148.   DOI
50 Kılıcoglu, T.; Ocak, Y. S. Microelectron. Eng. 2011, 88, 150.   DOI
51 Collado, D.; Casado, J.; Gonzalez, S. R.; Navarrete, J. T. L.; Suau, R.; Perez-Inestrosa, E.; Pappenfus, T. M.; Raposo, M. M. M. Chem. Eur. J. 2011, 17, 498.   DOI
52 Zhao, H.; Wang, B.; Liao, J.; Wang, H.; Tan, G. Tetrahedron Lett. 2013, 54, 6019.   DOI
53 Tsujimoto, K.; Ogasawara, R.; Fujiwara, H. Tetrahedron Lett. 2013, 54, 1251.   DOI