摘要
有机小分子太阳能电池材料是一类具有很大应用潜力的光伏材料,它具备了合成成本低,污染小,柔韧性好等诸多优点。同时,与聚合物材料相比又具有合成重复性好,容易提纯的优势。目前使用小分子给体材料的有机太阳能电池的光电转化效率大多在4%以下,而且与聚合物太阳能电池相比,对小分子BHJ结构电池尚缺乏系统的研究,新型材料稀少且效率相对较低。这也充分说明,发展新型有机太阳能电池小分子材料具有非常广泛的发展空间。因此设计合成溶解性、成膜性好,宽吸收,高电荷迁移率的小分子光伏材料成为我们研究的主要目标。
本论文先后使用了吡咯并吡咯烷酮结构(DPP)和1,3,5—均三嗪结构为中心来合成有机小分子光伏材料。
吡咯并吡咯烷酮结构(DPP)是由内酰胺构成的共轭平面双环结构,DPP类衍生物具有相对较低的HOMO、LUMO能级和较宽的吸收光谱。通过设计合成以DPP为核的共轭有机小分子可实现材料的宽吸收、高电荷传输性能。同时,通过在内酰胺结构的氮原子上引入烷基链可明显改善材料的溶解性及成膜性。本论文合成了三种以DPP为中心的有机小分子光伏材料,并且结合理论计算对三种材料的光物理与电化学性能进行了测试。三种材料的带隙宽度,LUMO与HOMO能级,吸收光谱范围都符合相应有机光伏材料的要求。其中D-A-D结构的小分子材料(DHFDPP)具有最好的成膜性,我们选择它作为光伏电池给体材料,通过溶液过程制备了本体异质结结构器件,对材料进行了初步的光伏性能测试,得到的能量转化效率为0.5%。器件的进一步优化还在进行中。
均三嗪结构是苯环上的1,3,5位碳原子被氮原子所取代的杂环芳烃,是一种强的吸电子基团,在配合物与光电材料方面有着广泛的应用,在太阳能电池领域研究较少。本论文使用2,4,6-三对甲酰基苯基-1,3,5-三嗪与对硝基苯乙氰为反应底物来合成小分子光伏材料。在合成反应底物2,4,6-三对甲酰基苯基-1,3,5-三嗪的过程中,发现使用Ni催化碳碳偶联反应可以在温和条件下合成均三嗪衍生物。因此本论文优化了这一合成方法,并合成了一系列的均三嗪衍生物。
Organic solar cells (OSCs) have attracted considerable interest due to their potential for large-scale, cost-effective and environmentally friendly power generation. In OSCs, small molecules (SMs) are of increasing interest due to their outstandingly high absorption coefficients and simple purification procedures in contrast to commonly used conjugated donor polymers, such as poly (3-hexylthiophene)(P3HT). However, most of the energy conversion efficiency obtained from the devices which used small molecule materials is in4%the following. Besides these, a small number of new materials and the lack of a systematic study of SMs research based on the bulk heterojunction (BHJ) concept are very obvious. That is to say the research of new small molecule materials for organic photovoltaic cells has very wide development space. So the main target of our research is to synthesize small molecule photovoltaic materials which have favourable solubility, wide absorption spectrum and high charge transfer efficiency.
In this article, we choose1,3,5-triazines and Diketopyrrolopyrrole (DPP) as the central structure to synthesize small molecule photovoltaic materials.
Diketopyrrolopyrrole (DPP) is a specific structure with two conjugate rings which is composed of the structures of lactams. The small molecules based on DPP have strong interaction because of the p-p functions. So the structure has low HOMO, LUMO and narrow energy band gap. Through the design and synthesis of small molecule materials based on DPP, we can synthesize the SMs which have wide absorption spectrum and high charge transfer efficiency. And by contecting the alkyl chain to the N atom in the structure of lactam, the solubility of the small molecule can be improved obviously. In this article, we have synthesized three small molecule photovoltaic materials based on DPP. And according to the theoretical calculation result, we have tested the HOMO, LUMO and the absorption spectrum of the materials, all of which meet the demand of being OSCs materials. Among the three small molecule materials, the structure of DHFDPP has the best ability of forming the film. So we used this material as the donor and made the solution-processed bulk heterojunction device. Then we tested the photovoltaic performance of the device and the energy conversion efficiency is0.5%, the work of optimizating the device is still in progress.
The structure of triazines is a strong electron withdrawing group. The derivatives of the triazines have been widely used in many respects, such as metal complexes, liquid crystal materials and organic photoelectronic materials. But few articles have reported the OSCs materials based on triazines. So we use the2,4,6-tris(4-formyl radical)benyl-1,3,5-triazines and the nitrophenyl acetonitrile as the raw materials to synthesize the small molecule OSCs materials. In the progress of synthesizing the2,4,6-tris(4-formyl radical)benyl-1,3,5-triazines, we found that the derives of1,3,5-triazines can be synthesized thourgh the Ni catalyst reactions under mild conditions. So we have optimizated the synthesis method and synthesized a series of derives based on1,3,5-triazines.
引文
[1]Mishra, A.; Bauerle, P., Small Molecule Organic Semiconductors on the Move:Promises for Future Solar Energy Technology [J]. Angewandte Chemie International Edition 2012,51 (9),2020-2067
[2]Dou, L.; You, J.; Yang, J.; Chen, C.-C.; He, Y.; SeiichiroMurase; Moriarty, T. Emery, K.; Li, G.; Yang, Y., Tandem polymer solar cells featuring a spectrally matched low-bandgap polymer[J]. Nature photonics 2012,6,180-185
[3]Tamayo, A. B.; Tantiwiwat, M.; Walker, B.; Nguyen, T.-Q., Design, Synthesis, and Self-assembly of Oligothiophene Derivatives with a Diketopyrrolopyrrole Core [J]. Journal of Physical Chemistry C 2008,112,15543-15552
[4]Habas, S. E.; Platt, H. A. S.; Hest, M. F. A. M. v.; Ginley, D. S., Low-Cost Inorganic Solar Cells:From Ink To Printed Device[J]. Chemical Reviews 2010,110,6571-6594
[5]. Li, G.; Zhu, R.; Yang, Y., Polymer solar cells [J]. nature photonics 2012,6,153-161
[6]Tamayo, A. B.; Tantiwiwat, M.; Walker, B.; Nguyen, T.-Q., Design, Synthesis, and Self-assembly of Oligothiophene Derivatives with a Diketopyrrolopyrrole Core [J]. Journal of Physical Chemistry C 2008,112,15543-15552
[7]Walker, B.; Tamayo, A. B.; Dang, X.-D.; Zalar, P.; Seo, J. H.; Garcia, A.; Tantiwiwat, M.; Nguyen, T.-Q., Nanoscale Phase Separation and High Photovoltaic Efficiency in Solution-Processed, Small-Molecule Bulk Heterojunction Solar Cells[J]. Advanced Functional Materials 2009,19 (19),3063-3069
[8]Fitzner, R.; Reinold, E.; Mishra, A.; Mena-Osteritz, E.; Ziehlke, H.; Korner, C. Leo, K., Dicyanovinyl-Substituted Oligothiophenes:Structure-Property Relationships and Application in Vacuum-Processed Small-Molecule Organic Solar Cells. Advanced Functional Materials 2011,21,897-910
[9]Sun, X.; Zhou, Y.; Wu, W.; Liu, Y.; Tian, W.; Yu, G., X-Shaped Oligothiophenes as a New Class of Electron Donors for Bulk-Heterojunction Solar Cells[J]. Journal of Physical Chemistry B 2006,110,7702-7707
[10]Jeong, B.-S.; Choi, H.; Cho, N.; Min Ko, H.; Lim, W.; Song, K.; Kwan Lee, J.; Ko, J., Molecular engineering of Diketopyrrolopyrrole-based photosensitizer for solution processed small molecule bulk heterojunction solar cells[J]. Solar Energy Materials and Solar Cells 2011,95 (7),1731-1740
[11]Koehorst, R. B. M.; Boschloo, G. K.; Savenije, T. J.; Goossens, A.; Schaafsma, T. J., Spectral Sensitization of TiO2 Substrates by Monolayers of Porphyrin HeterodimersLj]. Journal of Physical Chemistry B 2000,104,2371-2377
[12]Xia, P. F.; Feng, X. J.; Lu, J.; Movileanu, R.; Tao, Y.; Baribeau, J.-M.; Wong, M. S., Triarylamino and Tricyanovinyl End-Capped Oligothiophenes with Reduced Optical Gap for Photovoltaic App li cat ions [J]. Journal of Physical Chemistry C 2008, 112,16714-16720
[13]Silvestri, F.; Irwin, M. D.; Beverina, L.; Facchetti, A.; Pagani, G. A.; Marks, T. J., Efficient Squaraine-Based Solution Processable Bulk-Heterojunction Solar Cells[J]. Journal of the American Chemical Society 2008,130,17640-17641
[14]Wang, S.; Mayo, E. I.; Perez, M. D.; Griffe, L.; Wei, G.; Djurovich, P. I.; Forrest, S. R.; Thompson, M. E., High efficiency organic photovoltaic cells based on a vapor deposited squaraine donor[J]. Applied Physics Letters 2009,94 (23),233304
[15]Wienk, M. M.; Turbiez, M.; Gilot, J.; Janssen, R. A. J., Narrow-Bandgap Diketo - Pyrrolo - Pyrrole Polymer Solar Cells:The Effect of Processing on the Performance[J]. Advanced Materials 2008,20 (13),2556-2560
[16]Norrman, K.; Madsen, M. V.; Gevorgyan, S. A.; Krebs, F. C., Degradation Patterns in Water and Oxygen of an Inverted Polymer Solar Cell[J]. Journal of the American Chemical Society 2010,132,16883-16892
[17]Wong, W.-Y.; Wang, X.-Z.; He, Z.; Chan, K.-K.; Djuris ˇ ic, A. B.; Cheung, K.-Y. Yip, C.-T.; Ng, A. M.-C.; Xi, Y. Y.; Mak, C. S. K.; Chan, W.-K., Tuning the Absorption, Charge Transport Properties, and Solar Cell Efficiency with the Number of Thienyl Rings in Platinum-Containing Poly(aryleneethynylene)s[J]. Journal of the American Chemical Society 2007,129,14372-14380
[18](a) Qu, S.; Wang, B.; Guo, F.; Li, J.; Wu, W.; Kong, C.; Long, Y.; Hua, J., New diketo-pyrrolo-pyrrole (DPP) sensitizer containing a furan moiety for efficient and stable dye-sensitized solar cells[J]. Dyes and Pigments 2012,92,1384-1394; (b) Warnan, J.; Favereau, L.; Pellegrin, Y.; Blart, E.; Jacquemin, D.; Odobel, F. A compact diketopyrrolopyrrole dye as efficient sensitizer in titanium dioxide dye-sensitized solar cells[J]. Journal of Photochemistry and Photobiology A: Chemistry 2011,226,7; (c) Qu, S.; Wu, W.; Hua, J.; Kong, C.; Long, Y.; Tian, H. New Diketopyrrolopyrrole (DPP) Dyes for Efficient Dye-Sensitized Solar Cells [J]. Journal of Physical Chemistry C 2010,114,1343-1349; (d) Guo, F.; SanyinQu; WenjunWu; JingLi; WeijiangYing; JianliHua, Synthesis andphotovoltaicperformanceofnewdiketopyrrolopyrrole(DPP)dyes for dye-sensitized solarcells[J]. Synthetic Metals 2010,160,1767-1773
[19]Hagberg, D. P.; Yum, J.-H.; Lee, H.; Angelis, F. D.; Marinado T.; Karlsson, K. M.; Humphry-Baker, R.; Sun, L.; Hagfeldt, A.; Gratzel, M.; Nazeeruddin, M. K. Molecular Engineering of Organic Sensitizers for Dye-Sensitized Solar Cell Applications[J]. Journal of the American Chemical Society 2008,130,6259-6266
[20]Modelli, A.; Jones, D.; Pshenichnyuk, S. A., Electron Attachment to Dye-Sensitized Solar Cell Components:Rhodanine and Rhodanine-3-acetic Acid[J]. Journal of Physical Chemistry C 2010,114,1725-1732
[21](a) Wienk, M. M.; Turbiez, M.; Gilot, J.; Janssen, R. A. J., Narrow-Bandgap Diketo-Pyrrolo-Pyrrole Polymer Solar Cells:The Effect of Processing on the Performance[J]. Advanced Materials 2008,20,5; (b) Bijleveld, J. C.; Zoombelt, A. P.; Mathijssen, S. G. J.; Wienk, M. M.; Turbiez, M.; Leeuw, D. M. d.; Janssen, R. A. J., Poly(diketopyrrolopyrrole-terthiophene) for Ambipolar Logic and Photovoltaics[J]. Journal of the American Chemical Society 2009,131,2; (c) Chao-YingYu; Chih-PingChen; Shu-HuaChan; Gue-WuuHwang, Thiophene/Phenylene/Thiophene-Based Low-Bandgap Conjugated Polymers for Efficient Near-Infrared Photovoltaic Applications [J]. Chemistry of Materials 2009, 21,8; (d) Liang, Y.; Feng, D.; Wu, Y.; Tsai, S.-T.; Li, G.; Ray, C.; Yu, L., Highly Efficient Solar Cell Polymers Developed via Fine-Tuning of Structural and Electronic Properties [J]. J. AM. CHEM. SOC 2009,131,8; (e) Zhang, G.; Liu, K. Fan, H.; Li, Y.; Zhan, X.; Li, Y.; Yang, M., The photovoltaic behaviors of PPV-and PPE-type conjugated polymers featured with diketopyrrolopyrrole (DPP) units [J]. Synthetic Metals 2009,159,5; (f) Zhou, E.; Yamakawa, S.; Tajima, K.; Yang, C. Hashimoto, K., Synthesis and Photovoltaic Properties of Diketopyrrolopyrrole-Based Donor-Acceptor Copolymers[J]. Chemistry of Materials 2009,21,4055-4061
[22]Chabinyc, M. L.; Toney, M. F.; Kline, R. J.; McCulloch, I.; Heeney, M., X-ray Scattering Study of Thin Films of Poly(2,5-bis(3-alkylthiophen-2-yl) thieno [3,2-b] thiophene) [J]. Journal of the American Chemical Society 2007,129, 3226-3237
[23]Shen, P.; Sang, G.; Lu, J.; Zhao, B.; Wan, M.; Zou, Y.; Li, Y.; Tan, S., Effect of 3D π-π Stacking on Photovoltaic and Electroluminescent Properties in Triphenylamine-containing Poly(p-phenylenevinylene) Derivatives[J]. Macromolecules 2008,41,5716-5722
[24](a) Blouin, N.; Michaud, A.; Gendron, D.; Wakim, S.; Blair, E.; Neagu-Plesu, R. te, M. B.; Durocher, G.; Tao, Y.; Leclerc, M., Toward a Rational Design of Poly(2,7-Carbazole) Derivatives for Solar Cells[J]. Journal of the American Chemical Society 2008,130,11; (b) Jurchescu,O. D.; Baas, J.; Palstra, T. T. M., Effect of impurities on the mobility of single crystal pentacene[J]. Applied Physics Letters 2004,84 (16),3061; (c) Karpe, S.; Cravino, A.; Frere, P.; Allain, M.; Mabon, G.; Roncali, J.,3D π-Conjugated Oligothiophenes Based on Sterically Twisted Bithiophene Nodes[J]. Advanced Functional Materials 2007,17 (7), 1163-1171; (d) Seo, J. H.; Park, D. S.; Cho, S. W.; Kim, C. Y.; Jang, W. C.; Whang, C. N.; Yoo, K. H.; Chang, G. S.; Pedersen, T.; Moewes, A.; Chae, K. H.; Cho, S. J., Buffer layer effect on the structural and electrical properties of rubrene-based organic thin-film transistors[J]. Applied Physics Letters 2006,89 (16),163505; (e) Takeya, J.; Yamagishi, M.; Tominari, Y.; Hirahara, R.; Nakazawa, Y.; Nishikawa, T.; Kawase, T.; Shimoda, T.; Ogawa, S., Very high-mobility organic single-crystal transistors with in-crystal conduction channels[J]. Applied Physics Letters 2007,90 (10),102120
[25]Lloyd, M. T.; Mayer, A. C.; Subramanian, S.; Mourey, D. A.; Herman, D. J.; Bapat, A. V.; Anthony, J. E.; Malliaras, G. G., Efficient Solution-Processed Photovoltaic Cells Based on an Anthradithiophene/Fullerene Blend [J]. Journal of the American Chemical Society 2007,129,9144-9149
[26]Kronenberg, N. M.; Deppisch, M.; Wurthner, F.; Lademann, H. W. A.; Deing, K. Meerholz, K., Bulk heterojunction organic solar cells based on merocyanine colorants[J]. Chemical Communications 2008,48,6489-6491
[27]Reyes-Reyes, M.; Kim, K.; Dewald, J.; pez-Sandoval, R. n. L.; Avadhanula, A. Curran, S.; Carroll, D. L., Meso-Structure Formation for Enhanced Organic Photovoltaic Cells[J]. Organic letters 2005,7,5749-5753
[28]Tamayo, A. B.; Tantiwiwat, M.; Walker, B.; Nguyen, T.-Q., Design, Synthesis, and Self-assembly of Oligothiophene Derivatives with a Diketopyrrolopyrrole Core[J]. Journal of Physical Chemistry C 2008,112,15543-15552
[29]Wicklein, A.; Ghosh, S.; Sommer, M.; rthner, F. W.; Thelakkat, M., Self-Assembly of Semiconductor Organogelator Nanowires for Photoinduced Charge SeparationQ]. ACS NANO 2009,3,1107-1114
[30]Lee,O. P.; Yiu, A. T.; Beaujuge, P. M.; Woo, C. H.; Holcombe, T. W.; Millstone, J. E.; Douglas, J. D.; Chen, M. S.; Frechet, J. M. J., Efficient Small Molecule Bulk Heterojunction Solar Cells with High Fill Factors via Pyrene-Directed Molecular Self-Assembly[J]. Advanced Materials 2011,23 (45),5359-5363
[31]Wu, Z.; Li, A.; Fan, B.; Xue, F.; Adachi, C.; Ouyang, J., Phenanthrene-functionalized 3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-diones as donor molecules for solution-processed organic photovoltaic cells[J]. Solar Energy Materials and Solar Cells 2011,95 (8),2516-2523
[32]Dennler, G.; Scharber, M. C.; Ameri, T.; Denk, P.; Forberich, K.; ChristophWaldauf; Brabec, C. J., Design Rules for Donors in Bulk-Heterojunction Tandem Solar Cells-Towards 15%Energy-Conversion Efficiency[J]. advanced materials 2008,20, 579-584
[33]Burckstummer, H.; Kronenberg, N. M.; Gsanger, M.; Stolte, M.; Meerholz, K. Wurthner, F., Tailored merocyanine dyes for solution-processed BHJ solar cells[J]. Journal of Materials Chemistry 2010,20,240-244
[34]Silvestri, F.; Irwin, M. D.; Beverina, L.; Facchetti, A.; Pagani, G. A.; Marks, T. J., Efficient Squaraine-Based Solution Processable Bulk-Heterojunction Solar Cells[J]. Journal of the American Chemical Society 2008,130,17640-17641
[35]Huo, L.; Hou, J.; Chen, H.-Y.; Zhang, S.; Jiang, Y.; Chen, T. L.; Yang, Y., Bandgap and Molecular Level Control of the Low-Bandgap Polymers Based on 3,6-Dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione toward Highly Efficient Polymer Solar Cells[J]. Macromolecules 2009,42,6564-6571
[36]Marrocchi, A.; Silvestri, F.; Seri, M.; Facchetti, A.; Taticchi, A.; Marks, T. J., Conjugated anthracene derivatives as donor materials for bulk heterojunction solar cells:olefinic versus acetylenic spacers [J]. Chemical Communications 2009, (11),1380-1390
[37]Sun, X.; Zhou, Y.; Wu, W.; Liu, Y.; Tian, W.; Yu, G.; Qiu, W.; Chen, S.; Zhu, D., X-Shaped Oligothiophenes as a New Class of Electron Donors for Bulk-Heterojunction Solar Cells [J]. Journal of Physical Chemistry B 2006,110,7702-7707
[38]Wu, G.; Zhao, G.; He, C.; Zhang, J.; He, Q.; Chen, X.; Li, Y., Synthesis and photovoltaic properties of a star-shaped molecule with triphenylamine as core and benzo[1,2,5]thiadiazol vinylene as arms[J]. Solar Energy Materials and Solar Cells 2009,93 (1),108-113
[39]Shu, W.; Valiyaveettil, S., Intramolecular hydrogen bond assisted planarization and self-assembly of simple disc-shaped molecules in mesophasesElectronic supplementary information (ESI) available:synthetic procedures for compounds 1-3 and crystallographic details for 3[J]. Chemical Communications 2002, (13), 1350-1351
[40]. Leriche, P.; Piron, F.; Ripaud, E.; Frere, P.; Allain, M.; Roncali, J., Star-shaped triazine-thiophene conjugated systems[J]. Tetrahedron Letters 2009,50 (40), 5673-5676.
[41](a) Esteruelas, M. A.; Fernandez, I.; Herrera, A.; Martin-Ortiz, M. Martinez-Alvarez, R.; Olivan, M.; Onate, E.; Sierra, M. A.; Valencia, M., Multiple C-H Bond Activation of Phenyl-Substituted Pyrimidines and Triazines Promoted by an Osmium Polyhydride:Formation of Osmapolycycles with Three, Five, and Eight Fused Rings[J]. Organometallics 2010,29 (4),976-986; (b) Aragoni, M. C.; Arca, M.; Crespo, M.; Devillanova, F. A.; Hursthouse, M. B.; Huth, S. L.; Isaia, F. Lippolis, V.; Verani, G., Investigation on the reactivity of dithiophosphonato/dithiophosphato NiII complexes towards 2,4,6-tris-2-pyridyl-1,3,5-triazine:developments and new perspectives[J]. Dalton Transactions 2009, (14),2510-2523
[42]Zou, L.; Liu, Z.; Yan, X.; Liu, Y.; Fu, Y.; Liu, J.:Huang, Z.; Chen, X.; Qin, J., Star-Shaped D-π-A Molecules Containing a 2,4,6-Tri (thiophen-2-yl)-1,3,5-triazine Unit:Synthesis and Two-Photon Absorption Properties[J]. European Journal of Organic Chemistry 2009,2009 (32), 5587-5593
[43]Omer, K. M.; Ku, S.-Y.; Chen, Y.-C.; Wong, K.-T.; Bard, A. J., Electrochemical Behavior and Electrogenerated Chemiluminescence of Star-Shaped D-A Compounds with 1,3,5-Triazine Core and Substituted Fluorene Arms[J]. Journal of the American Chemical Society 2010,132,10944-10952
[44]Tamayo, A. B.; Dang, X.-D.; Walker, B.; Seo, J.; Kent, T.; Nguyen, T.-Q., A low band gap, solution processable oligothiophene with a dialkylated Diketopyrrolopyrrole chromophore for use in bulk heterojunction solar cells [J]. Applied Physics Letters 2009,94 (103301),4
[45]Jeong, B.-S.; HyunbongChoi; NaraCho; HayeMinKo; WoocherlLim; KihyungSong; KwanLee, J.; JaejungKo, Molecular engineering of Diketopyrrolopyrrole-based photo sensitizer for solution processed small molecule bulk heterojunction solar cells[J]. Solar Energy Materials & Solar Cells 2011,95,1731-1740
[46]Walker, B.; Tamayo, A. B.; Dang, X.-D.; Zalar, P.; Seo, J. H.:Garcia, A. Tantiwiwat, M.; Nguyen, T.-Q., Nanoscale Phase Separation and High Photovoltaic Efficiency in Solution-Processed, Small-Molecule Bulk Heterojunction Solar Cells[J]. Advanced Functional Materials 2009,19,3063-3069
[47]Sonar, P.; Ng, G.-M.; Lin, T. T.; Dodabalapur, A.; Chen, Z.-K., Solution processable low bandgap diketopyrrolopyrrole (DPP) based derivatives:novel acceptors for organic solar cells[J]. Journal of Materials Chemistry 2010,20, 3626-3636
[48]. Sonar, P.; Ng, G.-M.; Lin, T. T.; Dodabalapur, A.; Chen, Z.-K., Solution processable low bandgap diketopyrrolopyrrole (DPP) based derivatives:novel acceptors for organic solar cells[J]. Journal of Materials Chemistry 2010,20 (18), 3626-3636.
[49]Loser, S.; Bruns, C. J.; Miyauchi, H.; Ortiz, R. o. P.; Facchetti, A.; Stupp, S. 1.; Marks, T. J., A Naphthodithiophene-Diketopyrrolopyrrole Donor Molecule for Efficient Solution-Processed Solar Cells[J]. Journal of the American Chemical Society 2011,133 (21),8142-8145
[50]Aragoni, M. C.; Arca, M.; Crespo, M.; Devillanova, F. A.; Hursthouse, M. B.; Huth, S. L.; Isaia, F.; Lippolis, V.; Verani, G., Investigation on the reactivity of dithiophosphonato/dithiophosphato NiII complexes towards 2,4,6-tris-2-pyridyl-1,3,5-triazine:developments and new perspectives[J]. Dalton Transactions 2009, (14),2510-2520
[51]Santoni, M.-P.; Medlycott, E. A.; Hanan, G. S.; Hasenknopf, B.; Proust, A.; Nastasi, F.; Campagna, S.; Chiorboli, C.; Argazzi, R.; Scandola, F., Photoinduced energy transfer in a rod-like dinuclear Ru(Ⅱ) complex containing bis-pyridyl-1,3,5-triazine ligands[J]. Dalton Transactions 2009,3964-3970
[52]Hisamatsu, Y.; Aihara, H., Diverse dimerization of molecular tweezers with a 2,4,6-triphenyl-1,3,5-triazine spacer in the solid state[J]. Chemical Communications 2010,46 (27),4902-4904