Citation: Yan Jianfeng, Zhang Ruiqi, Yuan Ye, Yuan Yaofeng. 4, 4'-Dimethoxy-triphenylamine Conjugated Azobenzene Photochromic Switches:Synthesis, Electrochemical and Photoisomerization Studies[J]. Chinese Journal of Organic Chemistry, ;2019, 39(7): 2009-2017. doi: 10.6023/cjoc201902015 shu

4, 4'-Dimethoxy-triphenylamine Conjugated Azobenzene Photochromic Switches:Synthesis, Electrochemical and Photoisomerization Studies

Yan Jianfeng ^a ,
Zhang Ruiqi ^a ,
Yuan Ye ^a ,
Yuan Yaofeng ^a,b,,

a.
College of Chemistry, Fuzhou University, Fuzhou 350116
b.
State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002

Corresponding author: Yuan Yaofeng, yaofeng_yuan@fzu.edu.cn
Received Date: 18 February 2019
Revised Date: 10 March 2019
Available Online: 21 July 2019
Fund Project: the National Natural Science Foundation of China 21772023Project supported by the National Natural Science Foundation of China (No. 21772023), the Research Fund for the State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences (No. 20180020) and the Valuable Instrument and Equipment Open Test Fund of Fuzhou University (No. 2018T006)the Research Fund for the State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences 20180020the Valuable Instrument and Equipment Open Test Fund of Fuzhou University 2018T006

Figures(13)

Three azobenzenes 4~6 conjugated with 4, 4'-dimethoxy-triphenylamine redox center have been synthesized by palladium-catalyzed Sonogashira coupling reactions in moderate yield after column chromatographic purification. They are all stable when exposed in air and moisture in both the solid and solution state. The ¹H NMR spectra of 4~6 showned that the azobenzene groups are in the trans configuration. The UV/Vis spectra of the target molecule were studied. The UV/Vis absorption bands of 4~6 are less clearly separated, which is similar to those for aminoazobenzen or pseudostilbene. The absorption bands at the π→π^* band of 4 and 6 are redshifted, due to the strong electronic interaction between the azobenzene unit and the para-triphenylamine unit, which results in the formation of a longer conjugation system than the corresponding meta isomers. Electrochemical and spectroelectrochemical studies indicate excellent redox reversibility of these compounds. Significant spectra change upon the process of redox makes these compounds have potential applications of electrochemical switching. Among the derivatives, compound 4 exhibits the highest cis form (45%) in the photostationary state (PSS) upon light irradiation at 435 nm. The photoisomerization studies indicate that the photochemistry properties is strongly influenced by the substituted position of the triphenylamine moiety. Photoisomerization studies showed that these compounds have fast photoisomerization rate due to the higher photoisomerization quantum yield, which is an order of magnitude larger than that of ferrocenyl (ethynyl) azobenzenes. Both compounds 4 and 6 exhibit excellent fatigue resistance and reversibility under several repeated reversible isomerization cycles. The cis-to-trans photoisomerization of 4 can be not only achieved by irradiation at UV lignt, but also realized by a more efficient way of change the state of redox center. Our study will provide a good basis for research in design new type of multiple-response molecular switches.
- triphenylamine,
- azobenzene,
- photoisomerization,
- redox
1. [1]
  (a) Klajn, R.; Stoddart, J. F.; Grzybowski, B. A. Chem. Soc. Rev. 2010, 39(6), 2203.
  (b) Natali, M.; Giordani, S. Chem. Soc. Rev. 2012, 41(10), 4010.
  (c) Bleger, D.; Hecht, S., Angew. Chem., Int. Ed. 2015, 54(39), 11338.
2. [2]
3. [3]
  (a) Sakamoto, A.; Hirooka, A.; Namiki, K.; Kurihara, M.; Murata, M.; Sugimoto, M.; Nishihara, H. Inorg. Chem. 2005, 44, 7547.
  (b) Kume, S.; Nishihara, H. Metal-based Photoswitches Derived from Photoisomerization Photofunctional Transition Metal Complexes, Ed.: Yam, V., Springer Berlin/Heidelberg, 2007, Vol. 123, p. 79.
  (c) Bianchi, A.; Delgado-Pinar, E.; García-España, E.; Giorgi, C.; Pina, F. Coord. Chem. Rev. 2013, 260, 156.
  (d) Moustafa, M. E.; McCready, M. S.; Puddephatt, R. J. Organometallics 2013, 32, 2552.
  (e) Samanta, A.; Ravoo, B. J. Chem. Eur. J. 2014, 20, 4966.
4. [4]
  (a) Maciejewski, A.; Jaworska-Augustyniak, A.; Szeluga, Z.; Wojtczak, J.; Karolczak, J. Chem. Phys. Lett. 1988, 153, 227.
  (b) Kikuchi, M.; Kikuchi, K.; Kokubun, H. Bull. Chem. Soc. Jpn. 1974, 47, 1331.
  (c) Farmilo, A.; Wilkinson, F. Chem. Phys. Lett. 1975, 34, 575.
  (d) Lee, E. J.; Wrighton, M. S. J. Am. Chem. Soc. 1991, 113, 8562.
  (e) Fery-Forgues, S.; Delavaux-Nicot, B. J. Photochem. Photobiol., A 2000, 132, 137.
5. [5]
  Sakamoto, R.; Kume, S.; Nishihara, H. Chem. Eur. J. 2008, 14(23), 6978.
6. [6]
  (a) Seo, E. T.; Nelson, R. F.; Fritsch, J. M.; Marcoux, L. S.; Leedy, D. W.; Adams, R. N. J. Am. Chem. Soc. 1966, 88, 3498.
  (b) Reynolds, R.; Line, L. L.; Nelson, R. F. J. Am. Chem. Soc. 1974, 96(4), 1087.
7. [7]
  Gritzner, G.; Kuta, J. Pure Appl. Chem. 1984, 56(4), 461. doi: 10.1351/pac198456040461
8. [8]
  Dei, D. K.; Lund, B. R.; Wu, J.; Simon, D.; Ware, T.; Voit, W. E.; MacFarlane, D.; Liff, S. M.; Smith, D. W. ACS Macro Lett. 2012, 2, 35.
9. [9]
  Tanino, T.; Yoshikawa, S.; Ujike, T.; Nagahama, D.; Moriwaki, K.; Takahashi, T.; Kotani, Y.; Nakano, H.; Shirota, Y. J. Mater. Chem. 2007, 17, 4953. doi: 10.1039/b711542c
10. [10]
  (a) Blevins, A. A.; Blanchard, G. J. J. Phys. Chem. B 2004, 108, 4962.
  (b) Rau, H. In Photochromism, Ed.: Dürr, H.; Bouas-Laurent, H., Elsevier Science, Amsterdam, 2003, p. 165.
11. [11]
12. [12]
  (a) Moustafa, M. E.; McCready, M. S.; Puddephatt, R. J. Organometallics 2012, 31, 6262.
  (b) Wazzan, N. A.; Richardson, P. R.; Jones, A. C. Photochem. Photobiol. Sci. 2010, 9, 968.
13. [13]
  Yan, J.-F.; Lin, D.-Q.; Wang, X.-G.; Wu, K.-Q.; Xie, L.-L.; Yuan, Y.-F., Chem. Asian J. 2015, 10, 614. doi: 10.1002/asia.201403327
14. [14]
  Horie, M.; Sakano, T.; Osakada, K.; Nakao, H. Organometallics 2004, 23, 18. doi: 10.1021/om034163i
15. [15]
  Asano, T.; Okada, T.; Shinkai, S.; Shigematsu, K.; Kusano, Y.; Manabe, O. J. Am. Chem. Soc. 1981, 103, 5161. doi: 10.1021/ja00407a034
16. [16]
  (a) Helmut, K. In CRC Handbook of Organic Photochemistry and Photobiology, Vols. 1& 2, CRC Press, Boca Raton, 2003.
  (b) Yager, K. G.; Barrett, C. J. In Intelligent Materials, Chapter 17, The Royal Society of Chemistry, Cambridge, 2008, p. 424.
  (c) García-Amorós, J.; Velasco, D. Beilstein J. Org. Chem. 2012, 8, 1003.
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