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

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

  • Corresponding author: ZHANG Min, zm2016@email.tjut.edu.cn DONG Xiandui, dxd@ciac.ac.cn
  • Received Date: 15 August 2017
    Revised Date: 4 September 2017
    Accepted Date: 4 September 2017
    Available Online: 8 April 2017

    Fund Project: the National Science Foundation of China 51473158the National Science Foundation of China 91233206The project was supported by the National Science Foundation of China (51473158, 91233206)

  • 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.
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    1. [1]

      O'Regan, B. C.; Grätzel, M. Nature 1991, 353, 737. doi: 10.1038/353737a0  doi: 10.1038/353737a0

    2. [2]

      Mishra, A.; Fischer, M. K. R.; Bäuerle, P. Angew. Chem. Int. Ed. 2009, 48, 2474. doi: 10.1002/anie.200804709  doi: 10.1002/anie.200804709

    3. [3]

      Imahori, H.; Umeyama, T.; Ito, S. Acc. Chem. Res. 2009, 42, 1809. doi: 10.1021/ar900034t  doi: 10.1021/ar900034t

    4. [4]

      Clifford, J. N.; Martínez-Ferrero, E.; Viterisi, A.; Palomares, E. Chem. Soc. Rev. 2011, 40, 1635. doi: 10.1039/B920664G  doi: 10.1039/B920664G

    5. [5]

      Wonneberger, C.; Li, H. Adv. Mater. 2012, 24, 613. doi: 10.1002/adma.201104447  doi: 10.1002/adma.201104447

    6. [6]

      Wu, Y.; Zhu, W. Chem. Soc. Rev. 2013, 42, 2039. doi: 10.1039/C2CS35346F  doi: 10.1039/C2CS35346F

    7. [7]

      Liang, M.; Chen, J. Chem. Soc. Rev., 2013, 42, 3453. doi: 10.1039/C3CS35372A  doi: 10.1039/C3CS35372A

    8. [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. doi: 10.1016/j.tet.2013.11.072  doi: 10.1016/j.tet.2013.11.072

    9. [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. doi: 10.1021/sc500234a  doi: 10.1021/sc500234a

    10. [10]

      Kakiage, K.; Aoyama, Y.; Yano, T.; Oya, K.; Fujisawa, J. I.; Hanaya, M. Chem. Commun. 2015, 51, 15894. doi: 10.1039/C5CC06759F  doi: 10.1039/C5CC06759F

    11. [11]

      Yao, Z.; Zhang, M.; Li, R.; Yang, L.; Qiao, Y.; Wang, P. Angew. Chem. Int. Ed. 2015, 127, 6092. doi: 10.1002/ange.201501195  doi: 10.1002/ange.201501195

    12. [12]

      Yao, Z.; Wu, H.; Li, Y.; Wang, J.; Zhang, J.; Zhang, M.; Guo, Y.; Wang, P. Energy Environ. Sci. 2015, 8, 3192. doi: 10.1039/C5EE02822A  doi: 10.1039/C5EE02822A

    13. [13]

      Yao, Z.; Zhang, M.; Wu, H.; Yang, L.; Li, R.; Wang, P. J. Am. Chem. Soc. 2015, 137, 3799. doi: 10.1021/jacs.5b01537  doi: 10.1021/jacs.5b01537

    14. [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. doi: 10.1039/C5QO00377F  doi: 10.1039/C5QO00377F

    15. [15]

      Yang, L.; Li, Y.; Chen, S.; Zhang, J.; Zhang, M.; Wang, P. Acta Phys. -Chim. Sin. 2016, 32, 329.  doi: 10.3866/PKU.WHXB201511031

    16. [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.  doi: 10.3866/PKU.WHXB201605031

    17. [17]

      Xiao, A.; Lu, H.; Zhao, Y.; Luo, G. G. Acta Phys. -Chim. Sin. 2016, 32, 2968.  doi: 10.3866/PKU.WHXB201609194

    18. [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.  doi: 10.3866/PKU.WHXB201705082

    19. [19]

      Ren, Y.; Liu, J.; Zheng, A.; Dong, X.; Wang, P. Adv. Sci. 2017, 1700099. doi: 10.1002/advs.201700099  doi: 10.1002/advs.201700099

    20. [20]

      Rehm, J. M.; McLendon, G. L.; Nagasawa, Y.; Yoshihara, K.; Moser, J.; Grätzel, M. J. Phys. Chem. 1996, 100, 9577. doi: 10.1021/jp960155m  doi: 10.1021/jp960155m

    21. [21]

      Tachibana, Y.; Rubtsov, I. V.; Montanari, I.; Yoshihara, K.; Klug, D. R.; Durrant, J. R. J. Photoch. Photobio. A 2001, 142, 215. doi: 10.1016/S1010-6030(01)00516-0  doi: 10.1016/S1010-6030(01)00516-0

    22. [22]

      Luo, L.; Lo, C. F.; Lin, C. Y.; Chang, I. J.; Diau, W. G. J. Phys. Chem. B 2006, 110, 410. doi: 10.1021/jp055365q  doi: 10.1021/jp055365q

    23. [23]

      Martín, C.; Ziółek, M.; Marchena, M.; Douhal, A. J. Phys. Chem. C 2011, 115, 23183. doi: 10.1021/jp203489u  doi: 10.1021/jp203489u

    24. [24]

      Adamo, C.; Jacquemin, D. Chem. Soc. Rev. 2013, 42, 845. doi: 10.1039/C2CS35394F  doi: 10.1039/C2CS35394F

    25. [25]

      Fakis, M.; Hrobárik, P.; Yushchenko, O.; Sigmundová, I.; Koch, M.; Rosspeintner, A.; Stathatos, E.; Vauthey, E. J. Phys. Chem. C 2014, 118, 28509. doi: 10.1021/jp509971q  doi: 10.1021/jp509971q

    26. [26]

      Ai, X.; Guo, J.; Anderson, N. A.; Lian, T. J. Phys. Chem. B 2004, 108, 12795. doi: 10.1021/jp0483977  doi: 10.1021/jp0483977

    27. [27]

      Fakis, M.; Stathatos, E.; Tsigaridas, G.; Giannetas, V.; Persephonis, P. J. Phys. Chem. C 2011, 115, 13429. doi: 10.1021/jp201143n  doi: 10.1021/jp201143n

    28. [28]

      Yang, L.; Chen, S.; Zhang, J.; Wang, J.; Zhang, M.; Dong, X.; Wang, P. J. Mater. Chem. A 2017, 5, 3514. doi: 10.1039/C6TA10506H  doi: 10.1039/C6TA10506H

    29. [29]

      Li, Y.; Wang, J.; Yuan, Y.; Zhang, M.; Dong, X.; Wang, P. Phys. Chem. Chem. Phys. 2017, 19, 2549. doi: 10.1039/C6CP07916D.  doi: 10.1039/C6CP07916D

    30. [30]

      Chen, S.; Yang, L.; Zhang, J.; Yuan, Y.; Dong, X.; Wang, P. ACS Photonics 2017, 4, 165. doi: 10.1021/acsphotonics.6b00772  doi: 10.1021/acsphotonics.6b00772

    31. [31]

      Li, R.; Zhang, M.; Yan, C.; Yao, Z.; Zhang, J.; Wang, P. ChemSusChem 2015, 8, 97. doi: 10.1002/cssc.201402806  doi: 10.1002/cssc.201402806

    32. [32]

      Yang, L.; Yao, Z.; Liu, J.; Wang, J.; Wang, P. ACS Appl. Mater. Inter. 2016, 8, 9839. doi: 10.1021/acsami.6b02075  doi: 10.1021/acsami.6b02075

    33. [33]

      Shank, C. V. Science 1986, 233, 1276. doi: 10.1126/Science.233.4770.1276  doi: 10.1126/Science.233.4770.1276

    34. [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. [35]

      McCamant, D. W.; Kukura, P.; Mathies, R. A. J. Phys. Chem. A2003, 107, 8208. doi: 10.1021/jp030147n  doi: 10.1021/jp030147n

    36. [36]

      Trotzky, S.; Hoyer, T.; Tuszynski, W.; Lienau, C.; Parisi, J. J. Phys. D: Appl. Phys. 2009, 42, 055105. doi: 10.1088/0022-3727/42/5/055105  doi: 10.1088/0022-3727/42/5/055105

    37. [37]

      Li, R.; Lv, X.; Shi, D.; Zhou, D.; Cheng, Y.; Zhang, G.; Wang, P. J. Phys. Chem. C 2009, 113, 7469. doi: 10.1021/jp900972v  doi: 10.1021/jp900972v

    38. [38]

      Wang, P.; Zakeeruddin, S. M.; Comte, P.; Charvet, R.; Humphry-Baker, R.; Grätzel, M. J. Phys. Chem. B 2003, 107, 14336. doi: 10.1021/jp0365965  doi: 10.1021/jp0365965

    39. [39]

      Liu, J.; Li, R.; Si, X.; Zhou, D.; Shi, Y.; Wang, Y.; Jing, X.; Wang, P. Energy Environ. Sci. 2010, 3, 1924. doi: 10.1021/jp0365965  doi: 10.1021/jp0365965

    40. [40]

      Cai, N.; Wang, Y.; Xu, M.; Fan, Y.; Li, R.; Zhang, M.; Wang, P. Adv. Funct. Mater. 2013, 23, 1846. doi: 10.1002/adfm.201202562  doi: 10.1002/adfm.201202562

    41. [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. doi: 10.1039/C3EE40375K  doi: 10.1039/C3EE40375K

    42. [42]

      Snellenburg, J. J.; Laptenok, S. P.; Seger, R.; Mullen, K. M.; van Stokkum, I. H. M.; J. Stat. Softw. 2012, 49, 1. doi: 10.18637/jss.v049.i03  doi: 10.18637/jss.v049.i03

    43. [43]

      Lanzani G., Nisoli M., De Silvestri S., Tubino R.. Chemical Physics Letters: Femtosecond vibrational and torsional energy redistribution in photoexcited oligothiophenes[J]. Elsevier: Holland, 1996,Vol. 251:pp. 339-345.

    44. [44]

      Glasbeek, M.; Zhang, H. Chem. Rev. 2004, 104, 1929. doi: 10.1021/cr0206723  doi: 10.1021/cr0206723

    45. [45]

      Amdursky, N.; Erez, Y.; Huppert, D. Acc. Chem. Res. 2012, 45, 1548. doi: 10.1021/ar300053p  doi: 10.1021/ar300053p

    46. [46]

      Nelson, T.; Fernandez-Alberti, S.; Roitberg, A. E.; Tretiak, S. Acc. Chem. Res. 2014, 47, 1155. doi: 10.1021/ar400263p  doi: 10.1021/ar400263p

    47. [47]

      Oliver, T. A. A.; Lewis, N. H. C.; Fleming, G. R. Proc. Natl. Acad. Sci. U.S.A. 2014, 111, 10061. doi: 10.1073/pnas.1409207111  doi: 10.1073/pnas.1409207111

    48. [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. [49]

      Shemesh, D.; Sobolewski, A. L.; Domcke, W. Phys. Chem. Chem. Phys. 2010, 12, 4899. doi: 10.1039/B927024H  doi: 10.1039/B927024H

    50. [50]

      Qian, J.; Brouwer, A. M. Phys. Chem. Chem. Phys. 2010, 12, 12562. doi: 10.1039/C003419C  doi: 10.1039/C003419C

    51. [51]

      O'Regan, B. C.; Durrant, J. R. Acc. Chem. Res. 2009, 42, 1799. doi: 10.1021/ar900145z  doi: 10.1021/ar900145z

    52. [52]

      Fabregat-Santiago, F.; Garcia-Belmonte, G.; Mora-Séro, I.; Bisquert, J. Phys. Chem. Chem. Phys. 2011, 13, 9083. doi: 10.1039/C0CP02249G  doi: 10.1039/C0CP02249G

    53. [53]

      Bisquert, J. ChemPhysChem 2011, 12, 1633. doi: 10.1002/cphc.201100248  doi: 10.1002/cphc.201100248

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