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

Abstract

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

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

References

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]	Qiuju Liang, Yinxia Chang, Chaowei Liang, Haolei Zhu, Zibin Guo, Jiangang Liu. Application of Crystallization Kinetics Strategy in Morphology Control of Solar Cells based on Nonfullerene Blends [J]. Acta Phys. -Chim. Sin., 2023, 39(7): 2212006-0.
[2]	Zhen Wei, Minjie Li, Wencong Lu. Theoretical Study of High-Efficiency Organic Dyes with Different Electron-Withdrawing Groups Based on R6 toward Dye-Sensitized Solar Cells [J]. Acta Phys. -Chim. Sin., 2021, 37(10): 1905084-.
[3]	Rui CHEN,Wei WANG,Tongle BU,Zhiliang KU,Jie ZHONG,Yong PENG,Shengqiang XIAO,Wei YOU,Fuzhi HUANG,Yibing CHENG,Zhengyi FU. Low-Cost Fullerene Derivative as an Efficient Electron Transport Layer for Planar Perovskite Solar Cells [J]. Acta Phys. -Chim. Sin., 2019, 35(4): 401-407.
[4]	Fangbin LIU,Jun LIU,Lixiang WANG. An Organoboron Compound with a Thienyl Substituent as an Electron Acceptor for Organic Solar Cells [J]. Acta Phys. -Chim. Sin., 2019, 35(3): 251-256.
[5]	Yang YANG,Xiu JIANG,Xiaowei ZHAN,Xingguo CHEN. Designing an Organic Acceptor with Unsymmetrical Structure Based on Rhodanine and Thiazolidine-2, 4-dione Units to Study the Structure–Property Relationship [J]. Acta Phys. -Chim. Sin., 2019, 35(3): 257-267.
[6]	Qingqing XU,Chunmei CHANG,Wanbin LI,Bing GUO,Xia GUO,Maojie ZHANG. Non-Fullerene Polymer Solar Cells Based on a New Polythiophene Derivative as Donor [J]. Acta Phys. -Chim. Sin., 2019, 35(3): 268-274.
[7]	Guoxiao JIA,Shaoqing ZHANG,Liyan YANG,Chang HE,Huili FAN,Jianhui HOU. Development of Benzodithiophene-Based A-D-A Small Molecules with Different Acceptor End Groups for Efficient Organic Solar Cells [J]. Acta Phys. -Chim. Sin., 2019, 35(1): 76-83.
[8]	Chiaki TOMINAGA,Dailo HIKOSOU,Issey OSAKA,Hideya KAWASAK. Ag₇(MBISA)₆ Nanoclusters Conjugated with Quinacrine for FRET-Enhanced Photodynamic Activity under Visible Light Irradiation [J]. Acta Phys. -Chim. Sin., 2018, 34(7): 805-811.
[9]	Shichao ZHOU,Guitao FENG,Dongdong XIA,Cheng LI,Yonggang WU,Weiwei LI. Star-Shaped Electron Acceptor based on Naphthalenediimide-Porphyrin for Non-Fullerene Organic Solar Cells [J]. Acta Phys. -Chim. Sin., 2018, 34(4): 344-347.
[10]	Jie HAN,Qiuju LIANG,Yi QU,Jiangang LIU,Yanchun HAN. Morphology Control of Non-fullerene Blend Systems Based on Perylene [J]. Acta Phys. -Chim. Sin., 2018, 34(4): 391-406.
[11]	Ping HE,Fanglong YUAN,Zifei WANG,Zhanao TAN,Louzhen FAN. Growing Carbon Quantum Dots for Optoelectronic Devices [J]. Acta Phys. -Chim. Sin., 2018, 34(11): 1250-1263.
[12]	Xia GUO,Qunping FAN,Chaohua CUI,Zhiguo ZHANG,Maojie ZHANG. Wide Bandgap Random Terpolymers for High Efficiency Halogen-Free Solvent Processed Polymer Solar Cells [J]. Acta Phys. -Chim. Sin., 2018, 34(11): 1279-1285.
[13]	Jun YUAN,Ye LIU,Can ZHU,Ping SHEN,Meixiu WAN,Liuliu FENG,Yingping ZOU. Asymmetric Quinoxaline-Based Polymer for High Efficiency Non-Fullerene Solar Cells [J]. Acta Phys. -Chim. Sin., 2018, 34(11): 1272-1278.
[14]	Jing ZHANG,Youjun HE,Jie MIN. Recent Progress in Hybrid Perovskite Solar Cells Based on p-Type Small Molecules as Hole Transporting Materials [J]. Acta Phys. -Chim. Sin., 2018, 34(11): 1221-1238.
[15]	Li-Gang XU, Wei QIU, Run-Feng CHEN, Hong-Mei ZHANG, Wei HUANG. Application of ZnO Electrode Buffer Layer in Perovskite Solar Cells [J]. Acta Physico-Chimica Sinica, 2018, 34(1): 36-48.

Ultrafast Photoluminescence Dynamics of Organic Photosensitizers with Conjugated Linkers Containing Different Heteroatoms

RichHTML

PDF

Like

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Metrics

Recommended 0