含不同杂原子共轭单元的有机光敏染料的超快发光动力学

doi:10.3866/PKU.WHXB201709082

摘要/Abstract

摘要：

系统研究了含有不同杂原子的共轭单元(联呋喃、联噻吩及联硒酚)的三种有机染料C210、C214和C216的超快发光动力学，双己氧基取代的三苯胺作为电子给体，氰基丙烯酸作为电子受体。详细考察了三种染料分别在不同媒介中的激发态动力学：四氢呋喃及甲苯溶液、聚甲基丙烯酸甲酯及聚苯乙烯聚合物薄膜、氧化铝及二氧化钛薄膜表面。发现在以上介质中都普遍存在动态斯托克斯位移现象，表明发生了非平衡激发态的分子内多步弛豫过程。由于扭转弛豫和电子注入过程之间的竞争作用，非平衡激发态的电子注入产率比平衡激发态的低得多。此外，由于激发态能量弛豫导致的能量损失，电子注入时间常数变化超过了一个数量级，这在未来的染料设计及器件发展中应进行控制。三种染料在平衡激发态处的电子注入效率相近，由于C210和C216加快的电子注入速率补足了它们较C214小的平衡激发态寿命。

关键词: 太阳电池, 激发态动力学, 有机染料, 超快光谱, 飞秒荧光上转换

Abstract:

The ultrafast photoluminescence dynamics of three organic dyes—C210, C214, and C216—with different conjugated linkers containing various heteroatoms, such as bifuran, bithiophene and biselenophene, in combination with dihexyloxy-substituted triphenylamine (TPA) as the electron donor and cyanoacrylic acid (CA) as the electron acceptor have been studied systematically. The excited-state dynamics of the three dyes were investigated in detail in different media: tetrahydrofuran (THF) and toluene (PhMe) solutions, polymethyl methacrylate (PMMA) and polystyrene (PS) polymer films, and the surfaces of alumina and titania films in contact with an ionic liquid composite electrolyte. These dyes were found to feature dynamic Stokes shifts in all the aforementioned media, indicating stepwise intramolecular relaxations of the non-equilibrium excited state. The electron injection yield was distinctly lower for the non-equilibrium excited state than the equilibrium excited states, which can be ascribed to the competition between torsional relaxation and electron injection. A broad time scale over one magnitude of order was presented for electron injection due to the great energy losses originating from the multiple torsional relaxations, which should be controlled for future dye design and device development. Moreover, despite the shorter lifetimes of the equilibrium excited states for C210 and C216 than C214, the electron injection yields of equilibrium excited states for all the dyes are comparable due to the accelerated electron injection rate.

Key words: Solar cells, Excited-state dynamics, Organic dyes, Ultrafast spectroscopy, Femtosecond fluorescence up-conversion

刘娇,霍继存,张敏,董献堆. 含不同杂原子共轭单元的有机光敏染料的超快发光动力学[J]. 物理化学学报, 2018, 34(4), 424-436. doi: 10.3866/PKU.WHXB201709082

Jiao LIU,Jicun HUO,Min ZHANG,Xiandui DONG. Ultrafast Photoluminescence Dynamics of Organic Photosensitizers with Conjugated Linkers Containing Different Heteroatoms[J]. Acta Phys. -Chim. Sin. 2018, 34(4), 424-436. doi: 10.3866/PKU.WHXB201709082

链接本文: https://www.whxb.pku.edu.cn/CN/10.3866/PKU.WHXB201709082

https://www.whxb.pku.edu.cn/CN/Y2018/V34/I4/424

参考文献

1	O'Regan B. C. ; Gr?tzel M. Nature 1991, 353, 737.
2	Mishra A. ; Fischer M. K. R. ; B?uerle P. Angew. Chem. Int. Ed. 2009, 48, 2474.
3	Imahori H. ; Umeyama T. ; Ito S. Acc. Chem. Res. 2009, 42, 1809.
4	Clifford J. N. ; Martínez-Ferrero E. ; Viterisi A. ; Palomares E. Chem. Soc. Rev. 2011, 40, 1635.
5	Wonneberger C. ; Li H. Adv. Mater. 2012, 24, 613.
6	Wu Y. ; Zhu W. Chem. Soc. Rev. 2013, 42, 2039.
7	Liang M. ; Chen J. Chem. Soc. Rev. 2013, 42, 3453.
8	Lin Y. Z. ; Huang C. H. ; Chang Y. J. ; Yeh C. W. ; Chin T. M. ; Chi K. M. ; Chou P. T. ; Watanabe M. ; Chow T. J. Tetrahedron 2014, 70, 262.
9	Li H. ; Yang Y. ; Hou Y. ; Tang R. ; Duan T. ; Chen J. ; Wang H. ; Han H. ; Peng T. ; Chen X. ; Li Q. ; Li Z. ACS Sustainable Chem. Eng. 2014, 2, 1776.
10	Kakiage K. ; Aoyama Y. ; Yano T. ; Oya K. ; Fujisawa J. I. ; Hanaya M. Chem. Commun. 2015, 51, 15894.
11	Yao Z. ; Zhang M. ; Li R. ; Yang L. ; Qiao Y. ; Wang P. Angew. Chem. Int. Ed. 2015, 127, 6092.
12	Yao Z. ; Wu H. ; Li Y. ; Wang J. ; Zhang J. ; Zhang M. ; Guo Y. ; Wang P. Energy Environ. Sci. 2015, 8, 3192.
13	Yao Z. ; Zhang M. ; Wu H. ; Yang L. ; Li R. ; Wang P. J. Am. Chem. Soc. 2015, 137, 3799.
14	Li H. ; Fang M. ; Xu T. ; Hou Y. ; Tang R. ; Chen J. ; Liu L. ; Han H. ; Peng T. ; Li Q. ; Li Z. Org. Chem. Front. 2016, 3, 233.
15	Yang L. ; Li Y. ; Chen S. ; Zhang J. ; Zhang M. ; Wang P. Acta Phys. -Chim. Sin. 2016, 32, 329.
15	杨林; 李阳; 陈淑; 张静; 张敏; 王鹏. 物理化学学报, 2016, 32, 329.
16	Weng X. L. ; Wang Y. ; Jia C. Y. ; Wan Z. Q. ; Chen X. M. ; Yao X. J. Acta Phys. -Chim. Sin. 2016, 32, 1990.
16	翁小龙; 王艳; 贾春阳; 万中全; 陈喜明; 姚小军. 物理化学学报, 2016, 32, 1990.
17	Xiao A. ; Lu H. ; Zhao Y. ; Luo G. G. Acta Phys. -Chim. Sin. 2016, 32, 2968.
17	肖岸; 卢辉; 赵阳; 骆耿耿. 物理化学学报, 2016, 32, 2968.
18	Li Z. G. ; Lu T. ; Gao H. ; Zhang Q. ; Li M. J. ; Ren W. ; Lu W. C. Acta Phys. -Chim. Sin. 2017, 33, 1789.
18	李重杲; 卢天; 高恒; 张庆; 李敏杰; 任伟; 陆文聪. 物理化学学报, 2017, 33, 1789.
19	Ren Y. ; Liu J. ; Zheng A. ; Dong X. ; Wang P. Adv. Sci. 2017, 1700099.
20	Rehm J. M. ; McLendon G. L. ; Nagasawa Y. ; Yoshihara K. ; Moser J. ; Gr?tzel M. J. Phys. Chem. 1996, 100, 9577.
21	Tachibana Y. ; Rubtsov I. V. ; Montanari I. ; Yoshihara K. ; Klug D. R. ; Durrant J. R. J. Photoch. Photobio. A 2001, 142, 215.
22	Luo L. ; Lo C. F. ; Lin C. Y. ; Chang I. J. ; Diau W. G. J. Phys. Chem. B 2006, 110, 410.
23	Martín C. ; Zió?ek M. ; Marchena M. ; Douhal A. J. Phys. Chem. C 2011, 115, 23183.
24	Adamo C. ; Jacquemin D. Chem. Soc. Rev. 2013, 42, 845.
25	Fakis M. ; Hrobárik P. ; Yushchenko O. ; SigmundováI. ; Koch M. ; Rosspeintner A. ; Stathatos E. ; Vauthey E. J. Phys. Chem. C 2014, 118, 28509.
26	Ai X. ; Guo J. ; Anderson N. A. ; Lian T. J. Phys. Chem. B 2004, 108, 12795.
27	Fakis M. ; Stathatos E. ; Tsigaridas G. ; Giannetas V. ; Persephonis P. J. Phys. Chem. C 2011, 115, 13429.
28	Yang L. ; Chen S. ; Zhang J. ; Wang J. ; Zhang M. ; Dong X. ; Wang P. J. Mater. Chem. A 2017, 5, 3514.
29	Li Y. ; Wang J. ; Yuan Y. ; Zhang M. ; Dong X. ; Wang P. Phys. Chem. Chem. Phys. 2017, 19, 2549.
30	Chen S. ; Yang L. ; Zhang J. ; Yuan Y. ; Dong X. ; Wang P. ACS Photonics 2017, 4, 165.
31	Li R. ; Zhang M. ; Yan C. ; Yao Z. ; Zhang J. ; Wang P. ChemSusChem 2015, 8, 97.
32	Yang L. ; Yao Z. ; Liu J. ; Wang J. ; Wang P. ACS Appl. Mater. Inter. 2016, 8, 9839.
33	Shank C. V. Science 1986, 233, 1276.
34	Fleming G. R. ; van Grondelle R. Current opinion in structural biology: Femtosecond spectroscopy of photosynthetic lightharvesting systems Elsevier: Holland, 1997, Vol. 7, pp. 738- 748.
35	McCamant D. W. ; Kukura P. ; Mathies R. A. J. Phys. Chem. A 2003, 107, 8208.
36	Trotzky S. ; Hoyer T. ; Tuszynski W. ; Lienau C. ; Parisi J. J. Phys. D: Appl. Phys. 2009, 42, 055105.
37	Li R. ; Lv X. ; Shi D. ; Zhou D. ; Cheng Y. ; Zhang G. ; Wang P. J. Phys. Chem. C 2009, 113, 7469.
38	Wang P. ; Zakeeruddin S. M. ; Comte P. ; Charvet R. ; Humphry-Baker R. ; Gr?tzel M. J. Phys. Chem. B 2003, 107, 14336.
39	Liu J. ; Li R. ; Si X. ; Zhou D. ; Shi Y. ; Wang Y. ; Jing X. ; Wang P. Energy Environ. Sci. 2010, 3, 1924.
40	Cai N. ; Wang Y. ; Xu M. ; Fan Y. ; Li R. ; Zhang M. ; Wang P. Adv. Funct. Mater. 2013, 23, 1846.
41	Zhang J. ; Yao Z. ; Cai N. ; Yang L. ; Xu M. ; Li R. ; Zhang M. ; Dong X. ; Wang P. Energy Environ. Sci. 2013, 6, 1604.
42	Snellenburg J. J. ; Laptenok S. P. ; Seger R. ; Mullen K. M. ; van Stokkum I. H. M. J. Stat. Softw. 2012, 49, 1.
43	Lanzani G. ; Nisoli M. ; De Silvestri S. ; Tubino R. Chemical Physics Letters: Femtosecond vibrational and torsional energy redistribution in photoexcited oligothiophenes Elsevier: Holland 1996, Vol. 251, pp. 339- 345.
44	Glasbeek M. ; Zhang H. Chem. Rev. 2004, 104, 1929.
45	Amdursky N. ; Erez Y. ; Huppert D. Acc. Chem. Res. 2012, 45, 1548.
46	Nelson T. ; Fernandez-Alberti S. ; Roitberg A. E. ; Tretiak S. Acc. Chem. Res. 2014, 47, 1155.
47	Oliver T. A. A. ; Lewis N. H. C. ; Fleming G. R. Proc. Natl. Acad. Sci. U.S.A. 2014, 111, 10061.
48	Klymchenko A. S. ; Demchenko A. R. Methods in Enzymology: Chapter 3 Multiparametric Probing of Microenvironment with Solvatochromic Fluorescent Dyes Elsevier: Holland, 2008, Vol. 450, pp. 37- 58.
49	Shemesh D. ; Sobolewski A. L. ; Domcke W. Phys. Chem. Chem. Phys. 2010, 12, 4899.
50	Qian J. ; Brouwer A. M. Phys. Chem. Chem. Phys. 2010, 12, 12562.
51	O'Regan B. C. ; Durrant J. R. Acc. Chem. Res. 2009, 42, 1799.
52	Fabregat-Santiago F. ; Garcia-Belmonte G. ; Mora-Séro I. ; Bisquert J. Phys. Chem. Chem. Phys. 2011, 13, 9083.
53	Bisquert J. ChemPhysChem 2011, 12, 1633.

[1]	张明旭, 周琪森, 梅馨怡, 陈婧萱, 邱俊明, 李修志, 李霜, 于牧冰, 秦朝朝, 张晓亮. 贫PbI₂基体的胶体量子点固体用于高效红外太阳能电池[J]. 物理化学学报, 2023, 39(3): 2210002 -0 .
[2]	纪军, 刘新, 黄浩, 蒋皓然, 段明君, 刘本玉, 崔鹏, 李英峰, 李美成. 钙钛矿同质结太阳电池研究进展[J]. 物理化学学报, 2021, 37(4): 2008095 - .
[3]	魏珍, 李敏杰, 陆文聪. 应用于染料敏化太阳能电池的基于染料R6的含有不同吸电子基团的有机染料的理论研究[J]. 物理化学学报, 2021, 37(10): 1905084 - .
[4]	GUPTA Monika,闫东,沈福刚,徐建中,詹传郎. 苝二酰亚胺:有机膦盐基双组份共混电子传输层及其开路电压接近1.0 V的非富勒烯聚合物太阳电池[J]. 物理化学学报, 2019, 35(5): 496 -502 .
[5]	袁俊,刘晔,朱灿,沈平,万梅秀,冯柳柳,邹应萍. 基于侧链不对称喹喔啉聚合物的高效非富勒烯太阳电池[J]. 物理化学学报, 2018, 34(11): 1272 -1278 .
[6]	郑江波,陈智明,胡志诚,张杰,黄飞. 新型基于二氟苯并噻二唑和双噻吩丙烯腈共轭聚合物的设计、合成及光伏性能[J]. 物理化学学报, 2017, 33(8): 1635 -1643 .
[7]	陈军军,史成武,张正国,肖冠南,邵章朋,李楠楠. 4.81%光电转换效率的全固态致密PbS量子点薄膜敏化TiO₂纳米棒阵列太阳电池[J]. 物理化学学报, 2017, 33(10): 2029 -2034 .
[8]	陈海龙,边红涛,郑俊荣. 基于超快多维振动光谱技术解析分子体系的三维空间构型[J]. 物理化学学报, 2017, 33(1): 40 -62 .
[9]	晒旭霞,李丹,刘双双,李浩,王鸣魁. 钙钛矿太阳电池吸光层材料研究进展[J]. 物理化学学报, 2016, 32(9): 2159 -2170 .
[10]	刘晓灵,宋继梅,董纳,胡刚,杨捷,司维,李文慧. 鳞状BiOBr/Bi₂WO₆的合成及其吸附性能[J]. 物理化学学报, 2016, 32(7): 1844 -1850 .
[11]	张雪,韩洋,柴双志,胡南滔,杨志,耿会娟,魏浩. Cu₂ZnSn(S,Se)₄薄膜太阳电池研究进展[J]. 物理化学学报, 2016, 32(6): 1330 -1346 .
[12]	刘雪朋,孔凡太,陈汪超,于婷,郭福领,陈健,戴松元. 有机空穴传输材料在钙钛矿太阳电池中的应用[J]. 物理化学学报, 2016, 32(6): 1347 -1370 .
[13]	周立,朱俊,徐亚峰,邵志鹏,张旭辉,叶加久,黄阳,张昌能,戴松元. 绝缘氧化物包覆对钙钛矿太阳电池性能及界面电荷复合动力学的影响[J]. 物理化学学报, 2016, 32(5): 1207 -1213 .
[14]	王艳青,李龙,聂林辉,李楠楠,史成武. 两步沉积法制备Br或Cl掺杂的有机-无机杂化钙钛矿太阳电池[J]. 物理化学学报, 2016, 32(11): 2724 -2730 .
[15]	杨林,李阳,陈淑,张静,张敏,王鹏. 有机染料敏化太阳电池中激发态弛豫和电子注入的超快光谱研究[J]. 物理化学学报, 2016, 32(1): 329 -336 .