Browse > Article
http://dx.doi.org/10.9713/kcer.2011.49.1.095

Synthesis and Characterization of Phenylene-Thiophene-Thieno[3,4-b]pyrazine Oligomer  

Hwang, Mi-Lim (Division of Chemical Engineering, Chonbuk National University)
Li, Ji-Cheng (Division of Chemical Engineering, Chonbuk National University)
Seo, Eun-Ok (Division of Chemical Engineering, Chonbuk National University)
Lee, Soo-Hyoung (Division of Chemical Engineering, Chonbuk National University)
Lee, Youn-Sik (Division of Chemical Engineering, Chonbuk National University)
Publication Information
Korean Chemical Engineering Research / v.49, no.1, 2011 , pp. 95-100 More about this Journal
Abstract
During the development of low band-gap organic materials(p-type semiconducting organic compounds) for organic solar cells, an oligomer consisting of 2,5-dioctyloxyphenylene(OP), 3-hexylthiophene(HT), and 2,3-dimethylthieno[ 3,4-b]pyrazine(TP) as repeat units, oligo(OP-HT-TP), was synthesized. The oligomer was amorphous in nature in the temperature range studied, and well soluble in common organic solvents such as chloroform. The maximum absorption wavelength was 716 nm in solid state. The band-gap and HOMO/LUMO energy levels of oligo(OP-HT-TP) were measured to be 1.20 eV and -5.27/4.04 eV, respectively. However, the absorbance of the oligomer at maximum absorption wavelength was less than one fifth of that of poly(3-hexylthiophene) which has been most frequently used in fabrication of organic solar cells.
Keywords
3-hexylthiophene; Dioctyloxybenzene; 3,4-Dimethylthienopyrazine; Low Band-gap Oligomer; Organic Solar Cell;
Citations & Related Records
Times Cited By KSCI : 3  (Citation Analysis)
연도 인용수 순위
1 Dhanabalan, A., van Duren, J. K. J., van Hal, P. A., van Dongen, J. L. J. and Janssen, R. A. J., "Synthesis and Characterization of a Low Bandgap Conjugated Polymer for Bulk Heterojunction Photovoltaic Cells," Adv. Funct. Mater., 11(4), 255-262(2001).   DOI   ScienceOn
2 Schilinsky, P., Waldauf, C. and Brabec, C. J., "Recombination, Loss Analysis in Polythiophene Based Bulk Heterojunction Photodetectors," Appl. Phys. Lett., 87(20), 3885-3887(2002).
3 Reyes-Reyes, M., Kim, K. K. and Carroll, D. L., "High-efficiency Photovoltaic Devices Based on Annealed Poly(3-hexylthiophene) and 1-(3-methoxycarbonyl)-propyl-1-phenyl(6,6)C61 Blends," Appl. Phys. Lett., 87(8), 83506(2005).   DOI   ScienceOn
4 Ma, W., Yang, C., Gong, X., Lee, K. and Heeger, A. J., "Thermally Stable, Efficient Polymer Solar Cells with Nanoscale Control of the Interpenetrating Network Morphology," Adv. Funct. Mater., 15(10), 1617-1622(2005).   DOI   ScienceOn
5 Kim, J. Y., Kim, S. H., Lee, H. -H., Lee, K., Ma, W., Gong, X. and Heeger, A. J., "New Architecture for High-Efficiency Polymer Photovoltaic Cells Using Solution-Based Titanium Oxide as an Opticl Spacer," Adv. Mater., 18(5), 572-576(2006).   DOI   ScienceOn
6 Koetse, M. M., Sweelssen, J., Hoekerd, K. T., Schoo, H. F. M., Veenstra, S. C., Kroon, J. M., Yang, X. and Loos, J., "Efficient Polymer: Polymer Bulk Heterojunction Solar Cells," Appl. Phys. Lett., 88(8), 083504(2006).   DOI   ScienceOn
7 Xia, Y. J., Su, X. H., He, Z. C., Ren, X., Wu, H. B., Cao, Y. and Fan, D. W., "An Alternating Copolymer Derived from Indolo[3,2-b]carbazole and 4,7-Di(thieno[3,2-b]thien-2-yl)-2,1,3-benzothiadiazole for Photovoltaic Cells," Macromol. Rapid Commun., 31(14), 1287-1292(2010).   DOI   ScienceOn
8 Mikroyannidis, J. A., Kabanakis, A. N., Balraju, P., Sharma, G. D., "Enhanced Performance of Bulk Heterojunction Solar Cells Using Novel Alternating Phenylenevinylene Copolymers of Low Band Gap with Cyanovinylene 4-Nitrophenyls," Macromolecules, 43(13), 5544-5553(2010).   DOI   ScienceOn
9 Liang, Y. Y., Xu, Z., Xia, J. B., Tsai, S. -T., Wu, Y., Li, G., Ray, C. and Yu, L., "For the Bright Future-Bulk Heterojunction Polymer Solar Cells with Power Conversion Efficiency of 7.4%," Adv. Mater., 22(20), E135-E138(2010).   DOI   ScienceOn
10 Li, J.-C., Seo, E.-O., Lee, S.-H. and Lee, Y.-S., "Synthesis and Characterization of An Alternating Copolymer Consisting of N-(2-ethylhexyl)carbazole and 2,3-dimethylthieno[3,4-b]pyrazine units," Macromol. Res., 18(3), 304-307(2010).   DOI   ScienceOn
11 Li, J.-C., Hwang, M.-L., Lee, E.-W., Lee, S.-H., Yu, S.-C. and Lee, Y.-S., "Synthesis and Characterization of N-(2-ethylhexyl)carbazole-2,3-bis(4-fluorophenyl))thieno[3,4-b]pyrazine Copolymer," Bull. Korean Chem. Soc., 31(7), 2073-2076(2010).   DOI   ScienceOn
12 Karsten, B. P., Viani, L., Gierschner, J., Cornil, J. and Janssen, R. A. J., "An Oligomer Study on Small Band Gap Polymers," J. Phys. Chem. A., 112(43), 10764-10773(2008).   DOI   ScienceOn
13 Winzenberg, K. N., Kemppinen, P., Fanchini, G., Bown, M., Collis, G. E., Forsyth, C. M., Hegedus, K., Singh, Th. B. and Watkins, S. E., "Dibenzo[b,def]chrysene Derivatives: Solution-Processable Small Molecules that Deliver High Power-Conversion Efficiencies in Bulk Heterojunction Solar Cells," Chem. Mater., 21(24), 5701-5703(2009).   DOI   ScienceOn
14 Moses, D., Dogariu, A. and Heeger, A. J., "Ultrafast Detection of Charged Photocarriers in Conjugated Polymers," Physical Review B., 61(14), 9373-9379(2000).   DOI   ScienceOn
15 Li, J.-C., Kim, S.-J., Lee, S. H., Zong, K. K. and Lee, Y.-S., "Synthesis and Characterization of a Thiophene-benzothiadiazole Copolymer," Macromol. Res., 17(5), 356-360(2009).   DOI   ScienceOn
16 Aubert, P.-H., Knipper, M., Groenendaal, L., Lutsen, L., Manca, J., Vanderzande, D., "Copolymers of 3,4-Ethylenedioxythiophene and of Pyridine Alterated with Fluorene or Phenylene Units: Synthesis, Optical Properties, and Devices," Macromolecules, 37(11), 4087-4098(2004).   DOI   ScienceOn
17 Li, J.-C., Seo, E.-O., Lee, S.-H. and Lee, Y.-S., "Synthesis and Characterization of an Alternating Copolymer Consisting of N-(2-ethylhexyl)carbazole and 2,3-dimethylthieno[3,4-b]pyrazine units," Macromol. Res., 18(3), 304-307(2010).   DOI   ScienceOn
18 Zhu, Y., Rabindranath, A. R., Beyerlein, T. and Tieke, B., "Highly Luminescent 1,4-Diketo-3,6-diphenylpyrrolo[3,4-c]pyrrole-(DPP-) Based Conjugated Polymers Prepared Upon Suzuki Coupling," Macromolecules, 40(19), 6981-6989(2007).   DOI   ScienceOn
19 Zoombelt, A. P., Fonrodona, M., Turbiez, M. G. R., Wienk, M. M. and Janssen, R. A. J., "Synthesis and Photovoltaic Performance of a Series of Small Band Gap Polymers," J. Mater. Chem., 19(30), 5336-5342(2009).   DOI   ScienceOn
20 Kim, J. Y., Lee, K. H., Coates, N. E., Moses, D. and Nguyen, T.-Q., Dante, M. and Heeger, A. J., "Efficient Tandem Polymer Solar Cells Fabricated by All-Solution Processing," Science, 317(5835), 222-225(2007).   DOI   ScienceOn