Electron Acceptors Based on an All-Carbon Donor–Acceptor Copolymer†
Jessica L. Jellison
Department of Chemistry and Biochemistry, Southern Illinois University, Carbondale, IL (USA) http://www.kyleplunkett.com
Search for more papers by this authorChe-Hsiung Lee
Department of Chemistry and Biochemistry, Southern Illinois University, Carbondale, IL (USA) http://www.kyleplunkett.com
Search for more papers by this authorXinju Zhu
Department of Chemistry and Biochemistry, Southern Illinois University, Carbondale, IL (USA) http://www.kyleplunkett.com
Search for more papers by this authorJordan D. Wood
Department of Chemistry and Biochemistry, Southern Illinois University, Carbondale, IL (USA) http://www.kyleplunkett.com
Search for more papers by this authorCorresponding Author
Prof. Kyle N. Plunkett
Department of Chemistry and Biochemistry, Southern Illinois University, Carbondale, IL (USA) http://www.kyleplunkett.com
Department of Chemistry and Biochemistry, Southern Illinois University, Carbondale, IL (USA) http://www.kyleplunkett.comSearch for more papers by this authorJessica L. Jellison
Department of Chemistry and Biochemistry, Southern Illinois University, Carbondale, IL (USA) http://www.kyleplunkett.com
Search for more papers by this authorChe-Hsiung Lee
Department of Chemistry and Biochemistry, Southern Illinois University, Carbondale, IL (USA) http://www.kyleplunkett.com
Search for more papers by this authorXinju Zhu
Department of Chemistry and Biochemistry, Southern Illinois University, Carbondale, IL (USA) http://www.kyleplunkett.com
Search for more papers by this authorJordan D. Wood
Department of Chemistry and Biochemistry, Southern Illinois University, Carbondale, IL (USA) http://www.kyleplunkett.com
Search for more papers by this authorCorresponding Author
Prof. Kyle N. Plunkett
Department of Chemistry and Biochemistry, Southern Illinois University, Carbondale, IL (USA) http://www.kyleplunkett.com
Department of Chemistry and Biochemistry, Southern Illinois University, Carbondale, IL (USA) http://www.kyleplunkett.comSearch for more papers by this authorThis work was supported by startup funds and a seed grant provided by Southern Illinois University.
Graphical Abstract
The Sonogashira cross-coupling polymerization of a dibrominated cyclopenta[hi]aceanthrylene and a diethynylfluorene derivative produced a donor–acceptor copolymer composed solely of cyclopenta-fused polycyclic aromatic hydrocarbons. The resulting polymer displays low band gaps (<1.5 eV), dual absorption bands, and electron-accepting behavior as demonstrated through fluorescence quenching of poly(3-hexylthiophene).
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References
- 1E. E. Havinga, W. ten Hoeve, H. Wynberg, Synth. Met. 1993, 55, 299–306.
- 2aB. C. Thompson, J. M. J. Fréchet, Angew. Chem. 2008, 120, 62–82;
10.1002/ange.200702506 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 58–77;
- 2bM. Zhang, H. N. Tsao, W. Pisula, C. Yang, A. K. Mishra, K. Müllen, J. Am. Chem. Soc. 2007, 129, 3472–3473;
- 2cC. Li, M. Liu, N. G. Pschirer, M. Baumgarten, K. Müllen, Chem. Rev. 2010, 110, 6817–6855;
- 2dA. Facchetti, Chem. Mater. 2011, 23, 733–758.
- 3aC. J. Brabec, C. Winder, N. S. Sariciftci, J. C. Hummelen, A. Dhanabalan, P. A. van Hal, R. A. J. Janssen, Adv. Funct. Mater. 2002, 12, 709–712;
- 3bJ. Peet, J. Y. Kim, N. E. Coates, W. L. Ma, D. Moses, A. J. Heeger, G. C. Bazan, Nat. Mater. 2007, 6, 497–500.
- 4aA. Facchetti, M. Mushrush, M.-H. Yoon, G. R. Hutchison, M. A. Ratner, T. J. Marks, J. Am. Chem. Soc. 2004, 126, 13859–13874;
- 4bY. Wang, M. D. Watson, Macromolecules 2008, 41, 8643–8647.
- 5aX. Guo, F. S. Kim, S. A. Jenekhe, M. D. Watson, J. Am. Chem. Soc. 2009, 131, 7206–7207;
- 5bF. S. Kim, X. Guo, M. D. Watson, S. A. Jenekhe, Adv. Mater. 2010, 22, 478–482;
- 5cH. Yan, Z. Chen, Y. Zheng, C. Newman, J. R. Quinn, F. Dötz, M. Kastler, A. Facchetti, Nature 2009, 457, 679–686.
- 6L. Gao, W. Senevirathna, G. Sauvé, Org. Lett. 2011, 13, 5354–5357.
- 7J. D. Wood, J. L. Jellison, A. D. Finke, L. Wang, K. N. Plunkett, J. Am. Chem. Soc. 2012, 134, 15783–15789.
- 8aB. D. Steinberg, E. A. Jackson, A. S. Filatov, A. Wakamiya, M. A. Petrukhina, L. T. Scott, J. Am. Chem. Soc. 2009, 131, 10537–10545;
- 8bA. Ayalon, A. Sygula, P.-C. Cheng, M. Rabinovitz, P. W. Rabideau, L. T. Scott, Science 1994, 265, 1065–1067.
- 9aH. Reisch, U. Wiesler, U. Scherf, N. Tuytuylkov, Macromolecules 1996, 29, 8204–8210;
- 9bE. J. Meijer, D. M. De Leeuw, S. Setayesh, E. V. Veenendaal, B.-H. Huisman, P. W. M. Blom, J. C. Hummelen, U. Scherf, T. M. Klapwijk, Nat. Mater. 2003, 2, 678–682.
- 10aA. R. Mohebbi, J. Yuen, J. Fan, C. Munoz, M. F. Wang, R. S. Shirazi, J. Seifter, F. Wudl, Adv. Mater. 2011, 23, 4644–4648;
- 10bA. R. Mohebbi, F. Wudl, Chem. Eur. J. 2011, 17, 2642–2646.
- 11L. T. Scott, M. S. Bratcher, S. Hagen, J. Am. Chem. Soc. 1996, 118, 8743–8744.
- 12H. A. Wegner, L. T. Scott, A. de Meijere, J. Org. Chem. 2003, 68, 883–887.
- 13aD. T. Chase, B. D. Rose, S. P. McClintock, L. N. Zakharov, M. M. Haley, Angew. Chem. 2011, 123, 1159–1162; Angew. Chem. Int. Ed. 2011, 50, 1127–1130;
- 13bD. T. Chase, A. G. Fix, B. D. Rose, C. D. Weber, S. Nobusue, C. E. Stockwell, L. N. Zakharov, M. C. Lonergan, M. M. Haley, Angew. Chem. 2011, 123, 11299–11302;
10.1002/ange.201104797 Google ScholarAngew. Chem. Int. Ed. 2011, 50, 11103–11106;
- 13cF. G. Brunetti, A. Varotto, N. A. Batara, F. Wudl, Chem. Eur. J. 2011, 17, 8604–8608.
- 14aT. Kawase, A. Konishi, Y. Hirao, K. Matsumoto, H. Kurata, T. Kubo, Chem. Eur. J. 2009, 15, 2653–2661;
- 14bM. Saito, M. Nakamura, T. Tajima, Chem. Eur. J. 2008, 14, 6062–6068.
- 15aH. Dang, M. A. Garcia-Garibay, J. Am. Chem. Soc. 2001, 123, 355–356;
- 15bH. Dang, M. Levitus, M. A. Garcia-Garibay, J. Am. Chem. Soc. 2002, 124, 136–143;
- 15cC. L. Eversloh, Y. Avlasevich, C. Li, K. Müllen, Chem. Eur. J. 2011, 17, 12756–12762;
- 15dH. Xia, D. Liu, X. Xu, Q. Miao, Chem. Commun. 2012, DOI: .
- 16T. Okamoto, Z. Bao, J. Am. Chem. Soc. 2007, 129, 10308–10309.
- 17P. M. Beaujuge, C. M. Amb, J. R. Reynolds, Acc. Chem. Res. 2010, 43, 1396–1407.
- 18aG. Sonmez, C. K. F. Shen, Y. Rubin, F. Wudl, Angew. Chem. 2004, 116, 1524–1528;
10.1002/ange.200352910 Google ScholarAngew. Chem. Int. Ed. 2004, 43, 1498–1502;
- 18bG. Sonmez, H. B. Sonmez, C. K. F. Shen, R. W. Jost, Y. Rubin, F. Wudl, Macromolecules 2005, 38, 669–675.
- 19B. F. Plummer, M. J. Hopkinson, J. H. Zoeller, J. Am. Chem. Soc. 1979, 101, 6779–6781.
- 20aS. A. Jenekhe, L. Lu, M. M. Alam, Macromolecules 2001, 34, 7315–7324;
- 20bG. L. Gibson, T. M. McCormick, D. S. Seferos, J. Am. Chem. Soc. 2012, 134, 539–547.