A NOVEL ACRYLONITRILE DERIVATIVE HAVING PHOTOVOLTAIC PERFORMANCE

Abstract

A new acrylonitrile derivative 3 (BPCPFA) which offer potential application as organic solar cell material was synthesized with three steps. The structures of the molecules synthesized in these steps were characterized using various spectral analyses. BPCPFA was investigated as an electron acceptor molecule in next generation organic solar cells. Theoretical prediction and experimental studies for photovoltaic performance were performed. Based on these results, it is concluded that BPCPFA with extended conjugated system has good and promising photovoltaic performance with Voc value as 0.96 V.

Keywords

• Conjugated systems,nitriles,organic solar cells,photovoltaics

References

1. Bloking J, T,Han X,Higgs A, T,Kastrop J, P,Pandey L,Norton J, E,Risko C,Chen C, E,Brédas J,L,McGehee M, D, Sellinger A. Solution-processed organic solar cells with power conversion efficiencies of 2.5% using benzothiadiazole/ımide-based acceptors. Chemistry of Materials. 2011; 23: 5484−5490.DOI: 10.1021/cm203111k.
2. Gunes S, Neugebauer H, Sariciftci N, S. Conjugated polymer-based organic solar cells. Chemical Reviews. 2007; 107: 1324–1338. DOI:10.1021/cr050149z.
3. Brabec C J, Gowrisanker S, Halls J J M, Laird D, Jia S, Williams S, P. Polymer-fullerene bulk-heterojunction solar cells. Advanced Materials. 2010; 22: 3839–3856. DOI:10.1002/adma.200903697.
4. Linac Y, and Zhan X. Non-fullerene acceptors for organic photovoltaics: an emerging horizon. Materials Horizons. 2014; 1: 470-488. DOI: 10.1039/c4mh00042k.
5. Babu D, D, Gachumale S, R, Anandan S, Adhikari A, V. New D-π-A type indole based chromogens for DSSC: design, synthesis and performance studies. Dyes and Pigment. 2015; 112: 183–191. DOI:10.1016/j.dyepig.2014.07.006.
6. Liang Y, Xu Z, Xia J, Tsai S, T, Wu Y, Li G, Ray C, Yu L. For the bright future-bulk heterojunction polymer solar cells with power conversion efficiency of 7.4%. Advanced Energy Materials.2010; 22: 135–138. DOI: 10.1002/adma.200903528.
7. Kazici M, Bozar S, Aydin-Yuksel S, Ongul F, Gokce H, Gunes S, Yorur-Goreci C. Nanotechnology theoretical and experimental investigations of a 2-(4-chlorophenyl)-3-{[5-(2-cyano-2- phenylethenyl)]furan-2-yl}acrylonitrile molecule as a potential acceptor in organic solar cells. Nanotechnology. 2016; 27: 234003 (9pp). DOI:10.1088/0957-4484/27/23/234003.
8. Eftaiha A F, Sun J-P, Hill I, G, Welch G, C. Recent advances of non-fullerene, small molecular acceptors for solution processed bulk heterojunction solar cells. Journal of Materials Chemistry A. 2014; 2: 1201–1213. DOI: 10.1039/C3TA14236A.

9. Mishra A, Bäuerle P. Small molecule organic semiconductors on the move: promises for future solar energy technology. Angewandte Chemie International Edition. 2012;51: 2020–2067. DOI:10.1002/anie.201102326.
10. Lu S-Li, Yang M-J, Bai F-L. Synthesis, Electrochemical, and Optical Properties of a Novel PPV/PPE Block-Copolymer. Macromolecular Rapid Communications. 2004; 25: 968-971. DOI:10.1002/marc.200400004.
11. Xu Y, Zhang H, Li F, Shen F, Wang H, Li X, Yu Y, Ma Y. Supramolecular interaction-induced self-assembly of organic molecules into ultra-long tubular crystals with wave guiding and amplified spontaneous emission. Journal of Materials Chemistry. 2012; 22: 1592–1597. DOI: 10.1039/C1JM14815J.
12. Nagamatsu S, Oku S, Kuramoto K, Moriguchi T, Takashima W, Okauchi T, Hayase S. Long-Tetm Air Stable n-Channel Organic Thin-Film Transistors Using 2,5Difluoro-1,4-phenylene-bis{2-[4-(trifluoromethyl)phenyl]acrylonitrie}.Applied Materials and Interfaces. 2014; 6: 3847–3852. DOI: 10.1021/am.404549e.
13. Ying A, Wang L, Qiu F, Hu H, Yang J. Magnetic nanoparticle supported amine: an efficient and environmental benign catalyst for versatile Knoevenagel condensation under ultrasound irradiation. Comptes Rendus Chimie. 2015; 18: 223–232. DOI:10.1016/j.crci.2014.05.012.
14. Yang C, Chen H, Chuang Y, Wu C, Chen C, Liao S, Wang T. Characteristic of triphenylamine-based dyes with multiple acceptors in application of dye-sentized solar cells. Journal of Power Sources. 2009; 188: 627-634. DOI:10.1016/j.powsour.2008.12.026.
15. Becke A, D. Densityfunctional thermochemistry: III. The role of exact exchange. Journal of Chemical Physics. 1993; 98: 5648–5652. http://dx.doi.org/10.1063/1.464913.
16. Karthighaa S, Kalainathana S, Raob K.U.M, Hamadac F, Yamadad M, Kondoe Y. Synthesis, growth, structural, optical, luminescence, surface and HOMO LUMO analysis of 2-[2-(4-cholro-phenyl)-vinyl]-1-methylquinolinium naphthalene-2-sulfonate organic single crystals grown by a slow evaporation technique. Journal of Crystal Growth. 2016 ; 436 :113-124. doi:10.1016/j.jcrysgro.2015.11.028.
17. Kim B. G, Ma Xiao, Chen C, Ie Y, Coir E.W, Hashemi H, Aso Y, Green P.F, Kieffer J, Kim J. Energy Level Modulation of HOMO, LUMO, and Band-Gap in Conjugated Polymers for Organic Photovoltaic Applications. Advanced Functional Materials.2013; 23: 439–445.
18. DOI: 10.1002/adfm.201201385.
19. Xie X, H, Shen W, He R, X, Li M. A density functional study of furofuran polymers as potential materials for polymer solar cells. Bulletin Korean Chemical Society 2013; 34: 2995–3004. DOI: 10.5012/bkcs.2013.34.10.2995.
20. Scharber M C. On the Efficiency Limit of Conjugated Polymer:Fullerene-Based Bulk Heterojunction Solar Cells. Advanced Materials. 2016; 28 : 1994–2001. DOI: 10.1002/adma.201504914.
21. Elumalai N. K, and Ashraf U. Open circuit voltage of organic solar cells: an in-depth review Energy and Environmental Science. 2016 ; 9 : 391-410. DOI: 10.1039/c5ee02871j.