Effect of electron-withdrawing groups in conjugated bridges: molecular engineering of organic sensitizers for dyesensitized solar cells

Jie SHI; Zhaofei CHAI; Runli TANG; Huiyang LI; Hongwei HAN; Tianyou PENG; Qianqian LI; Zhen LI

doi:10.1007/s12200-016-0567-6

[1] O’Regan B, Gr tzel M. A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO2 films. Nature, 1991, 353(6346): 737–740

[2] Hagfeldt A, Boschloo G, Sun L, Kloo L, Pettersson H. Dyesensitized solar cells. Chemical Reviews, 2010, 110(11): 6595– 6663

[3] Hardin B E, Snaith H J, McGehee M D. The renaissance of dyesensitized solar cells. Nature Photonics, 2012, 6(3): 162–169

[4] Joly D, Pellejà L, Narbey S, Oswald F, Chiron J, Clifford J N, Palomares E, Demadrille R. A robust organic dye for dye sensitized solar cells based on iodine/iodide electrolytes combining high efficiency and outstanding stability. Scientific Reports, 2014, 4: 4033

[5] Joly D, Pellejà L, Narbey S, Oswald F, Meyer T, Kervella Y, Maldivi P, Clifford J N, Palomares E, Demadrille R. Metal-free organic sensitizers with narrow absorption in the visible for solar cells exceeding 10% efficiency. Energy & Environmental Science, 2015, 8(7): 2010–2018

[6] Kang X, Zhang J, O’Neil D, Rojas A J, Chen W, Szymanski P, Marder S R, El-Sayed M A. Effect of molecular structure perturbations on the performance of the D-A-p-A dye sensitized solar cells. Chemistry of Materials, 2014, 26(15): 4486–4493

[7] Cui Y,Wu Y, Lu X, Zhang X, Zhou G, Miapeh F B, Zhu W,Wang Z S. Incorporating benzotriazole moiety to construct D-A-p-A organic sensitizers for solar cells: significant enhancement of open-circuit photovoltage with long alkyl group. Chemistry of Materials, 2011, 23(19): 4394–4401

[8] Pei K, Wu Y, Islam A, Zhang Q, Han L, Tian H, Zhu W. Constructing high-efficiency D-A-π-A-featured solar cell sensitizers: a promising building block of 2,3-diphenylquinoxaline for antiaggregation and photostability. ACS Applied Materials & Interfaces, 2013, 5(11): 4986–4995

[9] Lu X, Feng Q, Lan T, Zhou G, Wang Z S. Molecular engineering of quinoxaline-based organic sensitizers for highly efficient and stable dye-sensitized solar cells. Chemistry of Materials, 2012, 24(16): 3179–3187

[10] Shi J, Chen J, Chai Z,Wang H, Tang R, Fan K,Wu M, Han H, Qin J, Peng T, Li Q, Li Z. High performance organic sensitizers based on 11,12-bis(hexyloxy) dibenzo[a,c]phenazine for dye-sensitized solar cells. Journal of Materials Chemistry, 2012, 22(36): 18830–18838

[11] Yang J, Ganesan P, Teuscher J, Moehl T, Kim Y J, Yi C, Comte P, Pei K, Holcombe T W, Nazeeruddin M K, Hua J, Zakeeruddin S M, Tian H, Gr tzel M. Influence of the donor size in D-π-A organic dyes for dye-sensitized solar cells. Journal of the American Chemical Society, 2014, 136(15): 5722–5730

[12] Li X, Hu Y, Sanchez-Molina I, Zhou Y, Yu F, Haque S A, Wu W, Hua J, Tian H, Robertson N. Insight into quinoxaline containing D- π-A dyes for dye-sensitized solar cells with cobalt and iodine based electrolytes: the effect of π-bridge on the HOMO energy level and photovoltaic performance. Journal of Materials Chemistry A, Materials for Energy and Sustainability, 2015, 3(43): 21733–21743

[13] Ying W, Guo F, Li J, Zhang Q,Wu W, Tian H, Hua J. Series of new D-A-π-A organic broadly absorbing sensitizers containing isoindigo unit for highly efficient dye-sensitized solar cells. ACS Applied Materials & Interfaces, 2012, 4(8): 4215–4224

[14] Zhu W, Wu Y, Wang S, Li W, Li X, Chen J, Wang Z, Tian H. Organic D-A-π-A solar cell sensitizers with improved stability and spectral response. Advanced Functional Materials, 2011, 21(4): 756–763

[15] Wu Y, Marszalek M, Zakeeruddin S M, Zhang Q, Tian H, Gr tzel M, Zhu W. High-conversion-efficiency organic dye-sensitized solar cells: molecular engineering on D-A-π-A featured organic indoline dyes. Energy & Environmental Science, 2012, 5(8): 8261–8272

[16] Wu Y, Zhu W. Organic sensitizers from D-π-A to D-A-π-A: effect of the internal electron-withdrawing units on molecular absorption, energy levels and photovoltaic performances. Chemical Society Reviews, 2013, 42(5): 2039–2058

[17] Eom Y K, Choi I T, Kang S H, Lee J, Kim J, Ju M J, Kim H K. Thieno[3, 2-b] benzothiophene derivative as a new π-bridge unit in D-π-A structural organic sensitizers with over

[18] 47% efficiency for dye-sensitized solar cells. Advanced Energy Materials, 2015, 5(15): 1500300

[19] Wu Y, Zhu W H, Zakeeruddin S M, Gr tzel M. Insight into D-A-π- A structured sensitizers: a promising route to highly efficient and stable dye-sensitized solar cells. ACS Applied Materials & Interfaces, 2015, 7(18): 9307–9318

[20] Chai Z, Wu M, Fang M, Wan S, Xu T, Tang R, Xie Y, Mei A, Han H, Li Q, Li Z. Similar or totally different: the adjustment of the twist conformation through minor structural modification, and dramatically improved performance for dye-sensitized solar cell. Advanced Energy Materials, 2015, 5(18): 1500846

[21] Haid S, Marszalek M, Mishra A, Wielopolski M, Teuscher J, Moser J E, Humphry-Baker R, Zakeeruddin S M, Gr tzel M, B uerle P. Significant improvement of dye-sensitized solar cell performance by small structural modification in π-conjugated donor-acceptor dyes. Advanced Functional Materials, 2012, 22(6): 1291–1302

[22] Yen Y S, Chou H H, Chen Y C, Hsu C Y, Lin J T. Recent developments in molecule-based organic materials for dye-sensitized solar cells. Journal of Materials Chemistry, 2012, 22(18): 8734–8747

[23] Liang M, Chen J. Arylamine organic dyes for dye-sensitized solar cells. Chemical Society Reviews, 2013, 42(8): 3453–3488

[24] Koumura N, Wang Z S, Mori S, Miyashita M, Suzuki E, Hara K. Alkyl-functionalized organic dyes for efficient molecular photovoltaics. Journal of the American Chemical Society, 2006, 128(44): 14256–14257

[25] Yamamoto T, Sugiyama K, Kushida T, Inoue T, Kanbara T. Preparation of new electron-accepting π-conjugated polyquinoxalines. Chemical and electrochemical reduction, electrically conducting properties, and use in light-emitting diodes. Journal of the American Chemical Society, 1996, 118(16): 3930–3937

[26] Blouin N, Michaud A, Gendron D, Wakim S, Blair E, Neagu-Plesu R, Belletête M, Durocher G, Tao Y, Leclerc M. Toward a rational design of poly(2,7-carbazole) derivatives for solar cells. Journal of the American Chemical Society, 2008, 130(2): 732–742

[27] Li H, Yang Y, Hou Y, Tang R, Duan T, Chen J, Wang H, Han H, Peng T, Chen X, Li Q, Li Z. Organic sensitizers featuring 9,10- diaryl-substituted anthracene unit. ACS Sustainable Chemistry & Engineering, 2014, 2(7): 1776–1784

[28] Li Q, Shi J, Li H, Li S, Zhong C, Guo F, Peng M, Hua J, Qin J, Li Z. Novel pyrrole-based dyes for dye-sensitized solar cells: from rodshape to “H” type. Journal of Materials Chemistry, 2012, 22(14): 6689–6696

[29] Li H, Hou Y, Yang Y, Tang R, Chen J, Wang H, Han H, Peng T, Li Q, Li Z. Attempt to improve the performance of pyrrole-containing dyes in dye sensitized solar cells by adjusting isolation groups. ACS Applied Materials & Interfaces, 2013, 5(23): 12469–12477

[30] Frisch G W T M J, Schlegel H B, Scuseria G E, Robb M A, Cheeseman J R, Scalmani G, Barone V, Mennucci B, Petersson G A, Nakatsuji H, Caricato M, Li X, Hratchian H P, Izmaylov A F, Bloino J, Zheng G, Sonnenberg J L, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery J A Jr, Peralta J E, Ogliaro F, Bearpark M, Heyd J J, Brothers E, Kudin K N, Staroverov V N, Kobayashi R, Normand J, Raghavachari K, Rendell A,Burant J C, Iyengar S S, Tomasi J, Cossi M, Rega N, Millam J M, Klene M, Knox J E, Cross J B, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann R E, Yazyev O, Austin A J, Cammi R, Pomelli C, Ochterski J W, Martin R L, Morokuma K, Zakrzewski V G, Voth G A, Salvador P, Dannenberg J J, Dapprich S, Daniels A D, Farkas , Foresman J B, Ortiz J V, Cioslowski J, Fox D J. Gaussian, Inc., Wallingford CT. 2009

[31] Salvatori P, Marotta G, Cinti A, Anselmi C, Mosconi E, De Angelis F. Supramolecular interactions of chenodeoxycholic acid increase the efficiency of dye-sensitized solar cells based on a cobalt electrolyte. Journal of Physical Chemistry C, 2013, 117(8): 3874– 3887

[32] Tang J, Hua J, Wu W, Li J, Jin Z, Long Y, Tian H. New starburst sensitizer with carbazole antennas for efficient and stable dyesensitized solar cells. Energy & Environmental Science, 2010, 3 (11): 1736–1745

[33] Wang Q, Moser J E, Gr tzel M. Electrochemical impedance spectroscopic analysis of dye-sensitized solar cells. Journal of Physical Chemistry B, 2005, 109(31): 14945–14953

[34] Adachi M, Sakamoto M, Jiu J, Ogata Y, Isoda S. Determination of parameters of electron transport in dye-sensitized solar cells using electrochemical impedance spectroscopy. Journal of Physical Chemistry B, 2006, 110(28): 13872–13880