Tuning the Light Absorption of Donor–Acceptor Conjugated Polymers: Effects of Side Chains and ‘Spacer’ Units in Thieno[3,4-b]pyrazine-Fluorene Copolymers
Michael E. Mulholland A , Kristine L. Konkol A , Trent E. Anderson A , Ryan L. Schwiderski A and Seth C. Rasmussen A B
+ Author Affiliations
- Author Affiliations
A Department of Chemistry and Biochemistry, North Dakota State University, NDSU Department 2735, PO Box 6050, Fargo, ND 58108-6050, USA.
B Corresponding author. Email: seth.rasmussen@ndsu.edu
Australian Journal of Chemistry 68(11) 1759-1766 https://doi.org/10.1071/CH15241
Submitted: 2 May 2015 Accepted: 22 June 2015 Published: 21 July 2015
Abstract
Four donor–acceptor (D-A) copolymers of 2,3-difunctionalized thieno[3,4-b]pyrazine (TP) and 9,9-dioctylfluorene were prepared in order to illustrate the ability to tune the electronic and optical properties of TP-based D-A polymers by the choice of side chains on the TP unit. In addition, analogous polymers were prepared with and without thiophene spacer units in order to allow discussion of their effect on the material properties. This combination of effects allowed tuning of the band gap over the range of 1.6–2.1 eV. Full optical and electrochemical characterization is reported for all materials, as well as initial photovoltaic device data for representative materials.
References
[1] S. C. Rasmussen, in 100+ Years of Plastics: Leo Baekeland and Beyond (Eds E. T. Strom, S. C. Rasmussen) 2011, Ch. 10, pp. 147–163 (ACS Symposium Series, American Chemical Society: Washington, DC).[2] S. C. Rasmussen, Bull. Hist. Chem. 2014, 39, 64.
| 1:CAS:528:DC%2BC2cXhvFGjtrrL&md5=4fb219e9547ea96c3123a172059bbd9eCAS |
[3] S. C. Rasmussen, Bull. Hist. Chem. 2015, 40, in press
[4] R. McNeill, R. Siudak, J. H. Wardlaw, D. E. Weiss, Aust. J. Chem. 1963, 16, 1056.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF2cXjtFCltQ%3D%3D&md5=2538644bcf7cea62d5b5713a571a53fcCAS |
[5] B. A. Bolto, D. E. Weiss, Aust. J. Chem. 1963, 16, 1076.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF2cXks1Squg%3D%3D&md5=1f8bae2a36e5b56d3882a4e2a4581f16CAS |
[6] B. A. Bolto, R. McNeill, D. E. Weiss, Aust. J. Chem. 1963, 16, 1090.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF2cXks1Squw%3D%3D&md5=783b0318d61774b1e90ccf30154d9d09CAS |
[7] Handbook of Conducting Polymers, 3rd edn (Eds T. A. Skotheim, J. R. Reynolds) 2007 (CRC Press: Boca Raton, FL).
[8] Handbook of Thiophene-Based Materials (Eds I. F. Perepichka, D. F. Perepichka) 2009 (John Wiley & Sons: Hoboken, NJ).
[9] I. F. Perepichka, D. F. Perepichka, H. Meng, F. Wudl, Adv. Mater. 2005, 17, 2281.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtFCgsbnF&md5=c92c748981f972f18303b71f9669c726CAS |
[10] S. Günes, H. Neugebauer, N. S. Sariciftci, Chem. Rev. 2007, 107, 1324.
| Crossref | GoogleScholarGoogle Scholar | 17428026PubMed |
[11] A. C. Grimsdale, K. L. Chan, R. E. Martin, P. G. Jokisz, A. B. Holmes, Chem. Rev. 2009, 109, 897.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXit1emu7o%3D&md5=a3103f55d5246cc8671519c237bd6f9cCAS | 19228015PubMed |
[12] M. C. Scharber, N. S. Sariciftci, Prog. Polym. Sci. 2013, 38, 1929.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXovVWnu78%3D&md5=2d0efed00dae0977f5a177c5cc553949CAS | 24302787PubMed |
[13] C. B. Nielsen, I. McCulloch, Prog. Polym. Sci. 2013, 38, 2053.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXovVWntbw%3D&md5=507d2c294241eb811354ee56b2a4b730CAS |
[14] S. C. Rasmussen, S. J. Evenson, C. B. McCausland, Chem. Commun. 2015, 4528.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXhsFSnsr8%3D&md5=364cc69e07b2ec637701b02ea8f9c4f9CAS |
[15] D. M. de Leeuw, E. Cantatore, Mater. Sci. Semicond. Process. 2008, 11, 199.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXht1CrsbzI&md5=ecc5f4c7b71c103cdabeedfcffcb800cCAS |
[16] S. Logothetidis, A. Laskarakis, Eur. Phys. J. Appl. Phys. 2009, 46, 12502.
| Crossref | GoogleScholarGoogle Scholar |
[17] T. Sekitani, T. Someya, Adv. Mater. 2010, 22, 2228.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXmvVGnu78%3D&md5=81860785bd845f21ba03f70c9f9e5edcCAS | 20229571PubMed |
[18] J. Roncali, Chem. Rev. 1997, 97, 173.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXktFyktg%3D%3D&md5=5679c4644996539c83b2ceec6e069223CAS | 11848868PubMed |
[19] J. Roncali, Macromol. Rapid Commun. 2007, 28, 1761.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtVCmtrbO&md5=9257956c1eb77b2a387ea5546e70b73eCAS |
[20] S. C. Rasmussen, K. Ogawa, S. D. Rothstein, in Handbook of Organic Electronics and Photonics (Ed. H. S. Nalwa) 2008, Vol. 1, Ch. 1, pp. 1–50 (American Scientific Publishers: Stevenson Ranch, CA).
[21] S. C. Rasmussen, M. Pomerantz, in Handbook of Conducting Polymers, 3rd edn (Eds T. A. Skotheim, J. R. Reynolds) 2007, Vol. 1, Ch. 12, pp. 12-1–12-42 (CRC Press: Boca Raton, FL).
[22] S. C. Rasmussen, in Encyclopedia of Polymeric Nanomaterials (Eds K. Muellen, S. Kobayashi) 2015, pp. 1155–1166 (Springer: Heidelberg).
[23] S. C. Rasmussen, R. L. Schwiderski, M. E. Mulholland, Chem. Commun. 2011, 11394.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXht12jtbrI&md5=93010535a6701853796d807edf45b907CAS |
[24] M. E. Mulholland, R. L. Schwiderski, S. C. Rasmussen, Polym. Bull. 2012, 69, 291.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xislygt70%3D&md5=8c2c409062eac73b144e9abb94aeb531CAS |
[25] M. E. Mulholland, R. L. Schwiderski, S. J. Evenson, S. C. Rasmussen, Polym. Mater. Sci. Eng. 2012, 107, 36.
[26] R. L. Schwiderski, S. C. Rasmussen, Synth. Met. 2014, 193, 58.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXosVWkurs%3D&md5=3bd2ef1a1d7ac71380bc940826904507CAS |
[27] M. E. Mulholland, L. Wen, S. C. Rasmussen, Topol. Supramol. Polym. Sci. 2015, 2, 18.
| Crossref | GoogleScholarGoogle Scholar |
[28] L. Wen, J. P. Nietfeld, C. M. Amb, S. C. Rasmussen, Synth. Met. 2009, 159, 2299.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsV2itrfN&md5=eb7f9252f2bf297770d834fe34f913b4CAS |
[29] F. Wudl, M. Kobayashi, A. J. Heeger, J. Org. Chem. 1984, 49, 3382.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2cXltFWmsrg%3D&md5=a88df953b0948a52c6d7ee60ded2d0c9CAS |
[30] M. Kobayashi, N. Colaneri, M. Boysel, F. Wudl, A. J. Heeger, J. Chem. Phys. 1985, 82, 5717.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2MXkvFKqsLw%3D&md5=f32a2ccfa7ba730fcc79f0038ceac2bdCAS |
[31] E. E. Havinga, W. ten Hoeve, H. Wynberg, Polym. Bull. 1992, 29, 119.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK38XmtlCltrk%3D&md5=41b2b4d7edce0e70f165f0b1ec506ee2CAS |
[32] E. E. Havinga, W. ten Hoeve, H. Wynberg, Synth. Met. 1993, 55, 299.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXjtFOmsA%3D%3D&md5=91d3adc31c6586b70f502b0670a825e9CAS |
[33] L. Wen, J. P. Nietfeld, C. M. Amb, S. C. Rasmussen, J. Org. Chem. 2008, 73, 8529.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXht1WlsbjE&md5=9f443b3ec92c5b69c556d8be3c8c884cCAS | 18839993PubMed |
[34] R. L. Schwiderski, S. C. Rasmussen, J. Org. Chem. 2013, 78, 5453.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXnvFyit78%3D&md5=7119b49d4685d24be0255d89a9fb2c2bCAS | 23692204PubMed |
[35] E. Bundgaard, F. C. Krebs, Sol. Energy Mater. Sol. Cells 2007, 91, 954.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXkslChtb0%3D&md5=106c8f3af1f8119f12acaa4249f677a2CAS |
[36] Y.-J. Cheng, S.-H. Yang, C.-S. Hsu, Chem. Rev. 2009, 109, 5868.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtF2ltb3M&md5=356e7a374f173dbdb22fa8e0802c0703CAS | 19785455PubMed |
[37] E. Perzon, X. Wang, F. Zhang, W. Mammo, J. L. Delgado, P. de la Cruz, O. Inganas, F. Langa, M. R. Andersson, Synth. Met. 2005, 154, 53.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXpvVynu7o%3D&md5=f3ef32b03ed4e7081ff88073b648c4d8CAS |
[38] F. Zhang, E. Perzon, X. Wang, W. Mammo, M. R. Andersson, O. Inganas, Adv. Funct. Mater. 2005, 15, 745.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXktlSktLY%3D&md5=67ba19081fe8a20062a33aaefb1ff574CAS |
[39] S. Admassie, O. Inganas, W. Mammo, E. Perzon, M. R. Andersson, Synth. Met. 2006, 156, 614.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XltVWhsLo%3D&md5=596d46d088947b452bed43eb285a1203CAS |
[40] Y. Zhu, R. D. Champion, S. A. Jenekhe, Macromolecules 2006, 39, 8721.
[41] R. S. Ashraf, H. Hoppe, M. Shahid, G. Gobsch, S. Sensfuss, E. Klemm, J. Polym. Sci. Part A: Polym. Chem. 2006, 44, 6952.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtlCnt77K&md5=f8f1d264357c55ccbf932c37bce93d05CAS |
[42] W.-C. Wu, C.-L. Liu, W.-C. Chen, Polymer 2006, 47, 527.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XktFOlug%3D%3D&md5=e2654feffcfda5c4a3c88e2b461a96abCAS |
[43] C.-C. Kuo, C.-H. Lin, W.-C. Chen, Macromolecules 2007, 40, 6959.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXptFSmtr8%3D&md5=eff31a4cfba122f5df48c073d845a11cCAS |
[44] W.-Y. Lee, K.-F. Cheng, T.-F. Wang, C.-C. Chueh, W.-C. Chen, C.-S. Tuan, J.-L. Lin, Macromol. Chem. Phys. 2007, 208, 1919.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtVCmtr%2FN&md5=b38880d124c746075e3da114425ba19eCAS |
[45] T. A. Bull, L. S. C. Pingree, S. A. Jenekhe, D. S. Ginger, C. K. Luscombe, ACS Nano 2009, 3, 627.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXitFKisrY%3D&md5=e6484909e1b81cd3b6f9d26a0858b876CAS | 19228011PubMed |
[46] M. Helgesen, F. C. Krebs, Macromolecules 2010, 43, 1253.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhvVGmtg%3D%3D&md5=567920bdb3e1bfcc2019820c4c6a2da8CAS |
[47] E. Zhou, J. Cong, S. Yamakawa, Q. Wei, M. Nakamura, K. Tajima, C. Yang, K. Hashimoto, Macromolecules 2010, 43, 2873.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXit1Ohs7k%3D&md5=158806a628186087f929a4d8e3f48aa0CAS |
[48] C.-Y. Chao, H. Lim, C.-H. Chao, Polymer Prepr. 2010, 51, 715.
| 1:CAS:528:DC%2BC3cXhtlygur7J&md5=6e0de5e9ea63d9efc27ec7d8ab7b6f01CAS |
[49] W.-Y. Lee, K.-F. Cheng, T.-F. Wang, W.-C. Chen, F.-Y. Tsai, Thin Solid Films 2010, 518, 2119.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXmslKlsQ%3D%3D&md5=ef7622bdce909905c2689edc5ab92eb9CAS |
[50] H. Aoki, J. Kakuta, T. Yamaguchi, S. Nitahara, S. Ito, Polym. J. 2011, 43, 937.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhsVagur7J&md5=3b434705a88d99a95ea26639d65b971eCAS |
[51] N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXoslGiurg%3D&md5=2dbde3727f92da4d6bcdec200714546cCAS |
[52] Y.-J. Cheng, T.-Y. Luh, J. Organomet. Chem. 2004, 689, 4137.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhtVWgt7nM&md5=043fbfde831b63bb82f27fd7966321f3CAS |
[53] N. Blouin, A. Michaud, M. Leclerc, Adv. Mater. 2007, 19, 2295.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtFSktrfO&md5=d48203e9db750893469fc1230ae564d4CAS |
[54] Y. Zou, D. Gendron, R. Badrou-Aïch, A. Najari, Y. Tao, M. Leclerc, Macromolecules 2009, 42, 2891.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXjvFKrsLc%3D&md5=1d5b2d3de99d9bbb1012b1e9f2976425CAS |
[55] L. Wen, C. L. Heth, S. C. Rasmussen, Phys. Chem. Chem. Phys. 2014, 16, 7231.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXkvVGms7Y%3D&md5=1283eaedc9264d5301840fe6dc36087cCAS | 24608186PubMed |
[56] C. M. Cardona, W. Li, A. E. Kaifer, D. Stockdale, G. C. Bazan, Adv. Mater. 2011, 23, 2367.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXms1Sku7o%3D&md5=e6631d5e9b7dc713eb6c58e1a8ceec46CAS | 21462372PubMed |
[57] L. Pandey, C. Risko, J. E. Norton, J.-L. Brédas, Macromolecules 2012, 45, 6405.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtFWhsL7L&md5=8477a12dc0f79f976de5b043dfce55ccCAS |
[58] S. C. Rasmussen, J. C. Pickens, J. E. Hutchison, Chem. Mater. 1998, 10, 1990.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXktFWjsbg%3D&md5=ec11f0f0c8eed7bf558c8b674e756be3CAS |
[59] S. Y. Cho, A. C. Grimsdale, D. J. Jones, S. E. Watkins, A. B. Holmes, J. Am. Chem. Soc. 2007, 129, 11910.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXpvFOhsr0%3D&md5=d5e1b1216d928ebadc4175603dbfd3f0CAS | 17824613PubMed |
[60] D. D. Kenning, K. A. Mitchell, T. R. Calhoun, M. R. Funfar, D. J. Sattler, S. C. Rasmussen, J. Org. Chem. 2002, 67, 9073.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XoslCjsL8%3D&md5=f1773b9d24f21cb8f8f935a0786bc9dcCAS | 12467431PubMed |
[61] P. Anuragudom, P. P. Newaz, S. Phanichphant, T. R. Lee, Macromolecules 2006, 39, 3494.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28Xjs1Gmsrw%3D&md5=7c3dbd6a2f3706d0c6a6564edc6cd171CAS |
[62] C. Kitamura, S. Tanaka, Y. Yamashita, Chem. Mater. 1996, 8, 570.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XlvVCjtg%3D%3D&md5=6a0e8a02db28b233eac200947879b1aeCAS |
