Determination of HOMO levels of organic dyes in solid-state electrochemistry

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• 作者：Chunhe Yang (1)
  Aiwei Tang (1)
  Feng Teng (2)
  Kejian Jiang (3)
  
  1. Department of Chemistry ; School of Science ; Beijing Jiaotong University ; Beijing ; China
  2. Institute of Optoelectronic Technology ; School of Science ; Beijing Jiaotong University ; Beijing ; China
  3. Laboratory of New Materials ; Institute of Chemistry ; Chinese Academy of Sciences ; Beijing ; China
  
• 刊名：Journal of Solid State Electrochemistry
• 出版年：2015
• 出版时间：March 2015
• 年：2015
• 卷：19
• 期：3
• 页码：883-890
• 全文大小：1,990 KB
• 参考文献：1. O鈥橰egan, B, Gratzel, M (1991) A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO2 films. Nature 353: pp. 737-740 CrossRef
  2. Gratzel, M (2007) Photovoltaic and photoelectrochemical conversion of solar energy. Phil Trans R Soc A 365: pp. 993-1005 CrossRef
  3. Hamann, TW, Jensen, RA, Martinson, ABF, Ryswykac, H, Hupp, JT (2008) Advancing beyond current generation dye-sensitized solar cells. Energ Environ Sci 1: pp. 66-78 CrossRef
  4. Calogero, G, Marco, G, Caramori, S, Cazzanti, S, Argazzi, R, Bignozzi, C (2009) Natural dye senstizers for photoelectrochemical cells. Energ Environ Sci 2: pp. 1162-1172 CrossRef
  5. Meyer, G (2010) The 2010 Millennium technology grand prize: dye-sensitized solar cells. ACS Nano 4: pp. 4337-4343 CrossRef
  6. Yum J, Chen P, Gratzel M, Nazeeruddin M (2008) Recent developments in solid-state dye-sensitized solar cells. ChemSusChem 1(8鈥?):699鈥?07
  7. Li, B, Wang, L, Kang, B, Wang, P, Qiu, Y (2006) Review of recent progress in solid-state dye-sensitized solar cells. Sol Energ Mater Sol Cell 90: pp. 549-573 CrossRef
  8. Filipic, M, Berginc, M, Smole, F, Topic, M (2012) Analysis of electron recombination in dye-sensitized solar cell. Curr App Phys 12: pp. 238-246 CrossRef
  9. Jennings, J, Liu, Y, Wang, Q, Zakeeruddin, S, Gratzel, M (2011) The influence of dye structure on charge recombination in dye-sensitized solar cells. Phys Chem Chem Phys 13: pp. 6637-6648 CrossRef
  10. Clifford, J, Martinez-Ferrero, E, Viterisi, A, Palomares, E (2011) Sensitizer molecular structure-device efficiency relationship in dye sensitized solar cells. Chem Soc Rev 40: pp. 1635-1646 CrossRef
  11. Listorti, A, O鈥橰egan, B, Durrant, J (2011) Electron transfer dynamics in dye-sensitized solar cells. Chem Mater 23: pp. 3381-3399 CrossRef
  12. Peter, L, Duffy, N, Wang, R, Wijayantha, K (2002) Transport and interfacial transfer of electrons in dye-sensitized nanocrystalline solar cells. J Electroanal Chem 524: pp. 127-136 CrossRef
  13. Gratzel, M (2003) Dye-sensitized solar cells. J Photochem Photobio C: Photochem Rev 4: pp. 145-153 CrossRef
  14. Mulhern, K, Detty, M, Watson, D (2011) Aggregation-induced increase of the quantum yield of electron injection from chalcogenorhodamine dyes to TiO2. J Phys Chem C 115: pp. 6010-6018 CrossRef
  15. Ehret, A, Stuhl, L, Spitler, MT (2001) Spectral sensitization of TiO2 nanocrystalline electrodes with aggregated cyanine dyes. J Phys Chem B 105: pp. 9960-9965 CrossRef
  16. Kawasaki, M, Aoyama, S (2004) High efficiency photocurrent generation by two-dimensional mixed J-aggregates of cyanine dyes. Chem Commun 21: pp. 988-989 CrossRef
  17. Khazraji, AC, Hotchandani, S, Das, S, Kamat, PV (1999) Controlling dye (Merocyanine-540) aggregation on nanostructured TiO2 Films. An organized assembly approach for enhancing the efficiency of photosensitization. J Phys Chem B 103: pp. 4693-4700 CrossRef
  18. Pastore, M, Angelis, F (2009) Aggregation of organic dyes on TiO2 in dye-sensitized solar cells models: an ab initio investigation. ACS Nano 4: pp. 556-562 CrossRef
  19. Sayama, K, Tsukagoshi, S, Hara, K, Ohga, Y, Shinpou, A, Abe, Y, Suga, S, Arakawa, H (2002) Photoelectrochemical properties of J aggregates of benzothiazole merocyanine dyes on a nanostructured TiO2 film. J Phys Chem B 106: pp. 1363-1371 CrossRef
  20. Choi, H, Lee, JK, Song, KH, Song, K, Kanga, SO, Koa, J (2007) Synthesis of new julolidine dyes having bithiophene derivatives for solar cell. Tetrahedron 63: pp. 1553-1559 CrossRef
  21. Hagberg, DP, Edvinsson, T, Marinado, T, Boschloo, G, Hagfeldt, A, Sun, L (2006) A novel organic chromophore for dye-sensitized nanostructured solar cells. Chem Commun 4: pp. 2245-2247 CrossRef
  22. Thomas, KRJ, Hsu, Y-C, Lin, JT, Lee, K-M, Ho, K-C, Lai, C-H, Cheng, Y-M, Chou, P-T (2008) 2,3-Disubstituted thiophene-based organic dyes for solar cells. Chem Mater 20: pp. 1830-1840 CrossRef
  23. Kuang, K, Klein, C, Ito, S, Moser, J-E, Humphry-Baker, R, Zakeeruddin, SM, Gr盲tzel, M (2007) High molar extinction coefficient ion-coordinating ruthenium sensitizer for efficient and stable mesoscopic dye-sensitized solar cells. Adv Funct Mater 17: pp. 154-160 CrossRef
  24. D鈥橝ndrade, BW, Datta, S, Forrest, SR, Djurovich, P, Polikarpov, E, Thompson, ME (2005) Relationship between the ionization and oxidation potentials of molecular organic semiconductors. Org Electron 6: pp. 11-20 CrossRef
  25. Bach, U, Lupo, D, Comte, P, Moser, JE, Weiss枚rtel, F, Salbeck, H, Spreitzer, J, Gr盲tzel, M (1998) Solid-state dye-sensitized mesoporous TiO2 solar cells with high photon-to-electron conversion efficiencies. Nature 395: pp. 583-585 CrossRef
  26. Hodes, G, Cahen, D (2012) All-solid-state, semiconductor-sensitized nanoporous solar cells. Acc Chem Res 45: pp. 705-713 CrossRef
  27. Bandara, J, Weerasinghe, H (2006) Design of high-efficiency solid-state dye-sensitized solar cells using coupled dye mixtures. So Energ Mater Sol Cell 90: pp. 864-871 CrossRef
  28. Cappel, U, Smeigh, A, Plogmaker, S, Johansson, E, Rensmo, H, Hammarstrom, L, Hagfeldt, A, Boschloo, G (2011) Characterization of the interface properties and processes in solid state dye-sensitized solar cells employing a perylene sensitizer. J Phys Chem C 115: pp. 4345-4358 CrossRef
  29. Cha, S, Lee, Y, Kang, M, Kang, Y (2010) Correlation between ionic conductivity and cell performance in solid-state dye-sensitized solar cells employing polymer electrolyte. J Photochem Photobio A: Chem 211: pp. 193-196 CrossRef
  30. Nogueira, V, Longo, C, Nogueira, A, Soto-Oviedo, M, Paoli, M (2006) Solid-state dye-sensitized solar cell: improved performance and stability using a plasticized polymer electrolyte. J Photochem Photobio A: Chem 181: pp. 226-232 CrossRef
  31. Liu, Q, Jiang, K, Guan, B, Tang, Z, Pei, J, Song, Y (2011) A novel bulk heterojunction solar cell based on a donor鈥揳cceptor conjugated triphenylamine dye. Chem Commun 47: pp. 740-742 CrossRef
  32. Shang, H, Luo, Y, Guo, X, Huang, X, Zhan, X, Jiang, K, Meng, Q (2010) The effect of anchoring group number on the performance of dye-sensitized solar cells. Dye Pig 87: pp. 249-256 CrossRef
  33. Yang, CH, He, GF, Wang, RQ, Li, YF (1999) Solid-state electrochemical investigation of poly [2-methoxy, 5-(2鈥?ethyl-hexyloxy)-1,4-phenylene vinylene]. J Electroanal Chem 471: pp. 32-36 CrossRef
  34. Frisch, MJ, Trucks, GW, Schlegel, HB, Scuseria, GE, Robb, MA, Cheeseman, JR, Scalmani, G, Barone, V, Mennucci, B, Petersson, GA, Nakatsuji, H, Caricato, M, Li, X, Hratchian, HP, Izmaylov, AF, Bloino, J, Zheng, G, Sonnenberg, JL, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Vreven, T, Montgomery, JA, Peralta, JE, Ogliaro, F, Bearpark, M, Heyd, JJ, Brothers, E, Kudin, KN, Staroverov, VN, Kobayashi, R, Normand, J, Raghavachari, K, Rendell, A, Burant, JC, Iyengar, SS, Tomasi, J, Cossi, M, Rega, N, Millam, JM, Klene, M, Knox, JE, Cross, JB, Bakken, V, Adamo, C, Jaramillo, J, Gomperts, RE, Stratmann, O, Yazyev, AJ, Austin, R, Cammi, C, Pomelli, JW, Ochterski, R, Martin, RL, Morokuma, K, Zakrzewski, VG, Voth, GA, Salvador, P, Dannenberg, JJ, Dapprich, S, Daniels, AD, Farkas, O, Foresman, JB, Ortiz, JV, Cioslowski, J, Fox, DJ (2009) Gaussian 09w, version 7.0. Gaussian, Inc, Wallingford
  35. Yang, C, Tang, A, Teng, F (2013) The solid-state electrochemistry of CdS and Cu (I)-doped CdS nanocrystals. J Electrochem Soc 160: pp. H121-H125 CrossRef
  36. Sonmez, G, Meng, H, Wudl, F (2004) Organic polymeric electrochromic devices: polychromism with very high coloration efficiency. Chem Mater 16: pp. 574-580 CrossRef
  37. Marchesi, LFQP, Simoes, FR, Pocrifka, LA, Pereira, EC (2011) Investigation of polypyrrole degradation using electrochemical impedance spectroscopy. J Phys Chem B 115: pp. 9570-9575 CrossRef
  38. Karlsson, C, Jamstorp, E, Stromme, M, Sjodin, M (2012) Computational electrochemistry study of 16 isoindole-4,7-diones as candidates for organic cathode materials. J Phys Chem C 116: pp. 3793-3801 CrossRef
  39. Karthikeyan, CS, Wietasch, H, Thelakkat, M (2007) Highly efficient solid-state dye-sensitized TiO2 solar cells using donor-antenna dyes capable of multistep charge-transfer cascades. Adv Mater 19: pp. 1091-1095 CrossRef
  40. Haque, SA, Handa, S, Peter, K, Palomares, E, Thelakkat, M, Durrant, JR (2005) Supermolecular control of charge transfer in dye-sensitized nanocrystalline TiO2 films: towards a quantitative structure鈥揻unction relationship. Angew Chem Int Ed 44: pp. 5740-5744 CrossRef
  41. Wang, M, Xu, M, Shi, D, Li, R, Gao, F, Zhang, G, Yi, Z, Humphry-Baker, R, Wang, P, Zakeeruddin, SM, Gr盲tzel, M (2008) High-performance liquid and solid dye-sensitized solar cells based on a novel metal-free organic sensitizer. Adv Mater 20: pp. 4460-4463 CrossRef
  42. Abe, T, Fukuda, H, Iriyama, Y, Ogumi, Z (2004) Solvated Li-ion transfer at interface between graphite and electrolyte. J Electrochem Soc 151: pp. A1120-A1123 CrossRef
  43. Cai, K, Mu, W, Zhang, Q, Jin, Z, Wang, D (2010) Study on the application of N, N鈥?1,4-diethyl, triethylene, and diamine tetrafluoroborate in supercapacitors. Electrochem Solid Stat Lett 13: pp. A147-A149 CrossRef
  44. Hoshikawa, T, Ikebe, T, Kikuchi, R, Eguchi, K (2006) Effects of electrolyte in dye-sensitized solar cells and evaluation by impedance spectroscopy. Electrochim Acta 51: pp. 5286-5294 CrossRef
  45. Wang, M, Moon, S, Zhou, D, Formal, F, Cevey-Ha, N, Humphry-Baker, R, Gratzel, C, Wang, P, Zakeeruddin, S, Gratzel, M (2010) Enhanced-light-harvesting amphiphilic ruthenium dye for efficient solid-state dye-sensitized solar cells. Adv Funct Mater 20: pp. 1821-1826 CrossRef
  46. Namutdinova, G, Sensfuss, S, Schrodner, M, Hinsch, A, Sastrawan, R, Gerhard, D, Himmler, S, Wasserscheid, P (2006) Quasi-solid state polymer electrolytes for dye-sensitized solar cells: effect of the electrolyte components variation on the triiodide ion diffusion properties and charge-transfer resistance at platinum electrode. Solid State Ionics 177: pp. 3141-3146 CrossRef
  47. Premalal, E, Dematage, N, Kumara, G, Rajapakse, R, Shimomura, M, Murakami, K, Konno, A (2012) Preparation of structurally modified, conductivity enhanced-p-CuSCN and its application in dye-sensitized solid-state solar cells. J Power Sources 203: pp. 288-296 CrossRef
  48. Cornil, J, Karzazi, Y, Bredas, JL (2002) Negative differential resistance in phenylene ethynylene oligomers. J Am Chem Soc 124: pp. 3516-3517 CrossRef
  49. Xie, XN, Wang, J, Loh, KP, Wee, SAT (2009) Aggregates-induced dynamic negative differential resistance in conducting organic films. App Phys Lett 95: pp. 203302 CrossRef
  50. Majumder, C, Briere, T, Mizuseki, H, Kawazoe, Y (2002) Molecular resistance in a molecular diode: a case study of the substituted phenylethynyl oligomer. J Phys Chem A 106: pp. 7911-7914 CrossRef
  51. Emberly, EG, Kirczenow, G (2001) Current-driven conformational changes, charging, and negative differential resistance in molecular wires. Phys Rev B 64: pp. 125318 CrossRef
  52. Kratochvilova, I, Kocirik, M, Zambova, A, Mbindyo, J, Mallouk, TE, Mayer, TS (2002) Room temperature negative differential resistance in molecular nanowires. J Mater Chem 12: pp. 2927-2930 CrossRef
  53. Li, J, Tang, A, Li, X, Cao, Y, Wang, M, Ning, Y, Lv, L, Lu, Q, Lu, Y, Hu, Y, Hou, Y, Teng, F (2014) Negative differential resistance and carrier transport of electrically bistable devices based on poly(N-vinylcarbazole)-silver sulfide composites. Nanoscale Res Lett 9: pp. 128 CrossRef
  54. Li, Y, Cao, Y, Gao, J, Wang, D, Yu, G, Heeger, AJ (1999) Electrochemical properties of luminescent polymers and polymer light-emitting electrochemical cells. Synth Met 99: pp. 243-248 CrossRef
  55. Yang, C, Tang, A, Li, X, Jiang, K, Teng, F (2013) Electrochemical evaluation of the frontier orbitals of organic dyes in aqueous electrolyte. Electrochim Acta 102: pp. 108-112 CrossRef
  56. Takacs, CJ, Sun, Y, Welch, GC, Perez, LA, Liu, X, Wen, W, Bazan, GC, Heeger, AJ (2012) Solar cell efficiency, self-assembly, and dipole鈥揹ipole interactions of isomorphic narrow-band-gap molecules. J Am Chem Soc 134: pp. 16597-16606 CrossRef
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Physical Chemistry
  Analytical Chemistry
  Industrial Chemistry and Chemical Engineering
  Characterization and Evaluation Materials
  Condensed Matter
  Electronic and Computer Engineering
  
• 出版者：Springer Berlin / Heidelberg
• ISSN：1433-0768

文摘

The solid-state electrochemistry of organic dyes, TT(2-cyano-3-(4-hexyl-5-dimethyltriphenylamine-thien-2-yl)acrylic acid), TTNa(2-cyano-3-(4-hexyl-5-dimethyltriphenylamine-thien-2-yl)acrylic acid sodium salt), and TS(2-[5-(4-hexyl-5-dimethyltriphenylamine-thien-2-yl)methylene-4-oxo-2-thioxothiazolidin-3-yl]acetic acid), was investigated. The redox processes of the solid dyes are electrochemically quasi-reversible. The electrochemical oxidation behaviors of these dye are similar because of the identical donor moieties and the highest occupied molecular orbital (HOMO) distribution in the dyes as revealed by density functional theory (DFT) calculation. The AC impedance spectra show that the dye film shows negative differential resistance characteristics in the high-frequency range and finite diffusion responses in the low-frequency range at higher potentials, which indicates the nonlinear charge transport and limited diffusion of counterions in the solid-state film. The onset oxidation potential of the solid dyes in the cyclic voltammetry does not affected by the ion diffusion. The cyclic voltammetry can be employed to derive reliable HOMO and lowest unoccupied molecular orbital (LUMO) levels of the solid dyes.