journal article·2019-07Open access

Synthesis of a tetrazine–quaterthiophene copolymer and its optical, structural and photovoltaic properties

Astrid-Caroline Knall, Sebastian Franz Hoefler, Manuel Hollauf, Ferula Thaler, Sven Noesberger, Ilie Hanzu, Heike Ehmann, Mathias Hobisch, Stefan Spirk, Shuguang Wen, Renqiang Yang, Thomas Rath, Gregor Trimmel

Journal of Materials Science· Volume 54· Issue 13

Abstract

Herein, we report the synthesis of a novel, tetrazine-based conjugated polymer. Tetrazines have the benefit of being strong electron acceptors, while little steric hindrance is imposed on the flanking thiophene rings. Conversion of a suitably substituted nitrile precursor led to 3,6-bis(5-bromo-4-(2-octyldodecyl)thiophen-2-yl)-1,2,4,5-tetrazine (2OD-TTz). Palladium-catalyzed copolymerization of 2OD-TTz with a bithiophene monomer yielded an alternating tetrazine-quaterthiophene copolymer (PTz4T-2OD). The polymer PTz4T-2OD showed an optical band gap of 1.8 eV, a deep HOMO energy level of - 5.58 eV and good solubility. In combination with the non-fullerene acceptor ITIC-F, solar cells with power conversion efficiencies of up to 2.6% were obtained.
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OpenAlex topics: Organic Electronics and Photovoltaics · Conducting polymers and applications · Molecular Junctions and Nanostructures

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References (37)

Show source-provided references
1. Zhang S, Qin Y, Zhu J, Hou J (2018) Over 14% efficiency in polymer solar cells enabled by a chlorinated polymer donor. Adv Mater 30:180086810.1002/adma.201800868 ↗
2. Green MA, Hishikawa Y, Dunlop ED, Levi DH, Hohl-Ebinger J, Yoshita M, Ho-Baillie AWY (2019) Solar cell efficiency tables (Version 53). Prog Photovolt Res Appl 27:3–1210.1002/pip.3102 ↗
3. Yuan J, Zhang Y, Zhou L, Zhang G, Yip H-L, Lau TK, Lu X, Zhu C, Peng H, Johnson PA, Leclerc M, Cao Y, Ulanski J, Li Y, Zou Y (2019) Single-junction organic solar cell with over 15% efficiency using fused-ring acceptor with electron-deficient core. Joule. https://doi.org/10.1016/j.joule.2019.01.00410.1016/j.joule.2019.01.004 ↗
4. Meng L, Zhang Y, Wan X, Li C, Zhang X, Wang Y, Ke X, Xiao Z, Ding L, Xia R, Yip H-L, Cao Y, Chen Y (2018) Organic and solution-processed tandem solar cells with 17.3% efficiency. Science 361:1094–109810.1126/science.aat2612 ↗
5. Zhan C, Zhang X, Yao J (2015) New advances in non-fullerene acceptor based organic solar cells. RSC Adv 5:93002–9302610.1039/C5RA17715D ↗
6. Liang N, Jiang W, Hou J, Wang Z (2017) New developments in non-fullerene small molecule acceptors for polymer solar cells. Mater Chem Front 1:1291–130310.1039/C6QM00247A ↗
7. Chen W, Zhang Q (2017) Recent progress in non-fullerene small molecule acceptors in organic solar cells (OSCs). J Mater Chem C 5:1275–130210.1039/C6TC05066B ↗
8. Li S, Liu W, Li C-Z, Shi M, Chen H (2017) Efficient organic solar cells with non-fullerene acceptors. Small 13:170112010.1002/smll.201701120 ↗
9. Wadsworth A, Moser M, Marks A, Little MS, Gasparini N, Brabec CJ, Baran D, McCulloch I (2019) Critical review of the molecular design progress in non-fullerene electron acceptors towards commercially viable organic solar cells. Chem Soc Rev 48:1596–1625. https://doi.org/10.1039/c7cs00892a)10.1039/C7CS00892A ↗
10. Holliday S, Ashraf RS, Nielsen CB, Kirkus M, Röhr JA, Tan C-H, Collado-Fregoso E, Knall A-C, Durrant JR, Nelson J, McCulloch I (2015) A rhodanine flanked nonfullerene acceptor for solution-processed organic photovoltaics. J Am Chem Soc 137:898–90410.1021/ja5110602 ↗
11. Kuzmich A, Padula D, Ma H, Troisi A (2017) Trends in the electronic and geometric structure of non-fullerene based acceptors for organic solar cells. Energy Environ Sci 10:395–40110.1039/C6EE03654F ↗
12. Zhao W, Qian D, Zhang S, Li S, Inganäs O, Gao F, Hou J (2016) Fullerene-free polymer solar cells with over 11% efficiency and excellent thermal stability. Adv Mater 28:4734–473910.1002/adma.201600281 ↗
13. Han G, Guo Y, Ning L, Yi Y (2019) Improving the electron mobility of ITIC by end-group modulation: the role of fluorination and π-extension. Sol RRL 3:180025110.1002/solr.201800251 ↗
14. Wen S, Li Y, Rath T, Li Y, Wu Y, Bao X, Han L, Ehmann H, Trimmel G, Zhang Y, Yang R (2019) A benzobis(thiazole)-based copolymer for highly efficient non-fullerene polymer solar cells. Chem Mater 31:919–92610.1021/acs.chemmater.8b04265 ↗
15. Knall A-C, Slugovc C (2013) Inverse electron demand Diels–Alder (iEDDA)-initiated conjugation: a (high) potential click chemistry scheme. Chem Soc Rev 42:5131–514210.1039/c3cs60049a ↗
16. Liu Y, Zhao J, Li Z, Mu J, Ma W, Hu H, Jiang K, Lin H, Ade H, Yan H (2014) Aggregation and morphology control enables multiple cases of high-efficiency polymer solar cells. Nat Commun 5:529310.1038/ncomms6293 ↗
17. Zhang G, Xia R, Chen Z, Xiao J, Zhao X, Liu S, Yip H-L, Cao Y (2018) Overcoming space-charge effect for efficient thick-film non-fullerene organic solar cells. Adv Energy Mater 8:180160910.1002/aenm.201801609 ↗
18. Suman, Bagui A, Gupta V, Maurya KK, Singh SP (2016) High-performance non-fullerene acceptor derived from diathiafulvalene wings for solution-processed organic photovoltaics. J Phys Chem C 120:24615–2462210.1021/acs.jpcc.6b07778 ↗
19. Li Z, Ding J (2011) Bisfuran-s-tetrazine-based conjugated polymers: synthesis, characterization, and photovoltaic properties. Macromol Chem Phys 212:2260–226710.1002/macp.201100358 ↗
20. Baek M-J, Jang W, Lee S-H, Lee Y-S (2012) Synthesis of new alternating conjugated copolymers consisting of tetrazine/carbazole or tetrazine/fluorene derivatives along with thiophene spacers for photovoltaic applications. Synth Met 161:2785–279110.1016/j.synthmet.2011.10.020 ↗
21. Li Z, Ding J, Song N, Lu J, Tao Y (2010) Development of a new s-tetrazine-based copolymer for efficient solar cells. J Am Chem Soc 132:13160–1316110.1021/ja106052e ↗
22. Li Z, Ding J, Song N, Du X, Zhou J, Lu J, Tao Y (2011) Alternating copolymers of dithienyl-s-tetrazine and cyclopentadithiophene for organic photovoltaic applications. Chem Mater 23:1977–198410.1021/cm200330c ↗
23. Wen S, Dong Q, Cheng W, Li P, Xu B, Tian W (2012) A benzo[1,2-b:4,5-b′]dithiophene-based copolymer with deep HOMO level for efficient polymer solar cells. Sol Energy Mater Sol Cells 100:239–24510.1016/j.solmat.2012.01.025 ↗
24. Cheng W, Wu Z, Wen S, Xu B, Li H, Zhu F, Tian W (2013) Donor–acceptor copolymers incorporating polybenzo [1,2-b:4,5-b′] dithiophene and tetrazine for high open circuit voltage polymer solar cells. Org Electron 14:2124–213110.1016/j.orgel.2013.05.015 ↗
25. Ding J, Song N, Li Z (2010) Synthesis, characterization and photovoltaic applications of a low band gap polymer based on s-tetrazine and dithienosilole. Chem Commun 46:8668–867010.1039/c0cc02766a ↗
26. Yang F, Li C, Lai W, Zhang A, Huang H, Li W (2017) Halogenated conjugated molecules for ambipolar field-effect transistors and non-fullerene organic solar cells. Mater Chem Front 1:1389–139510.1039/C7QM00025A ↗
27. Steckler TT, Henriksson P, Mollinger S, Lundin A, Salleo A, Andersson MR (2014) Very low band gap thiadiazoloquinoxaline donor–acceptor polymers as multi-tool conjugated polymers. J Am Chem Soc 136:1190–119310.1021/ja410527n ↗
28. Quinton C, Alain-Rizzo V, Dumas-Verdes C, Clavier G, Vignau L, Audebert P (2015) Triphenylamine/tetrazine based π-conjugated systems as molecular donors for organic solar cells. New J Chem 39:9700–971310.1039/C5NJ02097B ↗
29. Quinton C, Chi S-H, Dumas-Verdes C, Audebert P, Clavier G, Perry JW, Alain-Rizzo V (2015) Novel s-tetrazine-based dyes with enhanced two-photon absorption cross-sections. J Mater Chem C 3:8351–835710.1039/C5TC00531K ↗
30. Fulmer GR, Miller AJM, Sherden NH, Gottlieb HE, Nudelman A, Stoltz BM, Bercaw JE, Goldberg KI (2010) NMR chemical shifts of trace impurities: common laboratory solvents, organics, and gases in deuterated solvents relevant to the organometallic chemist. Organometallics 29:2176–217910.1021/om100106e ↗
31. Gritzner G (1990) Polarographic half-wave potentials of cations in nonaqueous solvents. Pure Appl Chem 62:1839–185810.1351/pac199062091839 ↗
32. Liu C, Wang K, Hu X, Yang Y, Hsu CH, Zhang W, Xiao S, Gong X, Cao Y (2013) Molecular weight effect on the efficiency of polymer solar cells. ACS Appl Mater Interfaces 5:12163–1216710.1021/am404157t ↗
33. Sun Y, Seo JH, Takacs CJ, Seifter J, Heeger AJ (2011) Inverted polymer solar cells integrated with a low-temperature-annealed sol–gel-derived ZnO film as an electron transport layer. Adv Mater 23:1679–168310.1002/adma.201004301 ↗
34. Knall AC, Jones AOF, Kunert B, Resel R, Reishofer D, Zach PW, Kirkus M, McCulloch I, Rath T (2017) Synthesis of a conjugated pyrrolopyridazinedione–benzodithiophene (PPD–BDT) copolymer and its application in organic and hybrid solar cells. Monatsh Chem 148:855–86210.1007/s00706-017-1949-1 ↗
35. Brouwer F, Alma J, Valkenier H, Voortman TP, Hillebrand J, Chiechi RC, Hummelen JC (2011) Using bis(pinacolato)diboron to improve the quality of regioregular conjugated co-polymers. J Mater Chem 21:1582–159210.1039/C0JM02359K ↗
36. Hoefler SF, Rath T, Pastukhova N, Pavlica E, Scheunemann D, Wilken S, Kunert B, Resel R, Hobisch M, Xiao S, Bratina G, Trimmel G (2018) The effect of polymer molecular weight on the performance of PTB7-Th:O-IDTBR non-fullerene organic solar cells. J Mater Chem A 6:9506–951610.1039/C8TA02467G ↗
37. Ashraf RS, Schroeder BC, Bronstein HA, Huang Z, Thomas S, Kline RJ, Brabec CJ, Rannou P, Anthopoulos TD, Durrant JR, McCulloch I (2013) The influence of polymer purification on photovoltaic device performance of a series of indacenodithiophene donor polymers. Adv Mater 25:2029–203410.1002/adma.201300027 ↗