Citation: Peng Peizhen, Li Jing, Hou Bin, Xin Hanshen, Cheng Tanyu, Gao Xike. Design, Synthesis and Properties of Indacenodithiophene Derivatives End-Capped with Azulene[J]. Chinese Journal of Organic Chemistry, ;2020, 40(11): 3916-3924. doi: 10.6023/cjoc202005014 shu

Design, Synthesis and Properties of Indacenodithiophene Derivatives End-Capped with Azulene

Peng Peizhen ^a,b ,
Li Jing ^b ,
Hou Bin ^b ,
Xin Hanshen ^b ,
Cheng Tanyu ^a,, ,
Gao Xike ^b,,

a.
College of Chemistry and Materials Science, Shanghai Normal University, Shanghai 200234
b.
Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Corresponding author: Cheng Tanyu, tycheng@shnu.edu.cn Gao Xike, gaoxk@mail.sioc.ac.cn
Received Date: 6 May 2020
Revised Date: 22 May 2020
Available Online: 29 May 2020
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21522209, 21790362), and the Science and Technology Commission of Shanghai Municipality (Nos. 19XD1424700, 18JC1410600)the National Natural Science Foundation of China 21790362the Science and Technology Commission of Shanghai Municipality 19XD1424700the Science and Technology Commission of Shanghai Municipality 18JC1410600the National Natural Science Foundation of China 21522209

Figures(9)

Two isomers of azulene and indacenodithiophene (IDT)-based compounds 1 and 2 were designed and synthesized, according to the different connections of azulene unit with IDT through its electron-rich five-membered ring and the electron-deficient seven-membered ring, respectively. The UV-Vis spectra, electrochemical properties and proton-responsive properties of 1 and 2 were studied. Compounds 1 and 2 show obviously different physicochemical properties and device performance of organic field-effect transistors (OFET). Both compounds 1 and 2 have reversible proton response characteristics. The end absorption peaks of these two compounds are between 400 and 600 nm before protonation. With the addition of trifluoroacetic acid (TFA), the absorption peaks are red shifted to 550~850 nm. When they are protonated fully (TFA volume ratio is about 1%), they are red shifted about 200 and 177 nm, respectively. The color of compounds 1 and 2 in dichloromethane solution before protonation is red after the adequate protonation. It turned to blue and returned to its original color after the addition of triethylamine. OFET thin film devices of 1 and 2 showed an order of magnitude difference, with hole mobilities of 4.14×10^-3 and 1.05×10^-5 cm²·V^-1·s^-1, respectively. The different connections of IDT and azulene units through the electronic rich five-membered ring and the electronic deficient seven-membered ring of azulene greatly affect the materials' device performance as well as their physicochemical properties, providing valuable insights for developing azulene-based novel organic functional molecules.
- azulene,
- indacenodithiophene,
- isomer,
- organic field effect transistors
1. [1]
  Lemal, D. M.; Goldman, G. D. J. Chem. Educ. 1988, 65, 923. doi: 10.1021/ed065p923
2. [2]
  (a) Michl, J.; Thulstrup, E. W. Tetrahedron 1976, 32, 205.
  (b) Dong, J.; Zhang, H. Chin. Chem. Lett. 2016, 27, 1097.
  (c) Ou, L.; Zhou, Y.; Wu, B.; Zhu, L. Chin. Chem. Lett. 2019, 30, 1903.
3. [3]
  (a) Cristian, L.; Sasaki, I.; Lacroix, P. G.; Donnadieu, B.; Asselberghs, I.; Clays, K.; Razus, A. C. Chem. Mater. 2004, 16, 3543.
  (b) Migalska-Zalas, A.; El kouari, Y.; Touhtouh, S. Opt. Mater. 2012, 34, 1639.
  (e) Wang, X.; Ng, J. K.-P.; Jia, P.; Lin, T.; Cho, C. M.; Xu, J.; Lu, X.; He, C. Macromolecules 2009, 42, 5534.
4. [4]
  (a) Yamaguchi, Y.; Maruya, Y.; Katagiri, H.; Nakayama, K.-I.; Ohba, Y. Org. Lett. 2012, 14, 2316.
  (b) Yamaguchi, Y.; Ogawa, K.; Nakayama, K.-I.; Ohba, Y.; Katagiri, H. J. Am. Chem. Soc. 2013, 135, 19095.
  (c) Yamaguchi, Y.; Takubo, M.; Ogawa, K.; Nakayama, K.-I.; Koganezawa, T.; Katagiri, H. J. Am. Chem. Soc. 2016, 138, 1133.
  (d) Xin, H.; Li, J.; Ge, C.; Yang, X.; Xue, T.; Gao, X. Mater. Chem. Front. 2018, 2, 975.
  (e) Xin, H.; Ge, C.; Jiao, X.; Yang, X.; Rundel, K.; McNeill, C. R.; Gao, X. Angew. Chem. Int. Ed. 2018, 57, 1322.
  (f) Xin, H.; Ge, C.; Gao, H.; Yang, X.; Gao, X. Chem. Sci. 2016, 7, 6701.
5. [5]
  (a) Xia, J.; Capozzi, B.; Wei, S.; Strange, M.; Batra, A.; Moreno, J. R.; Amir, R. J.; Amir, E.; Solomon, G. C.; Venkataraman, L. Nano Lett. 2014, 14, 2941.
  (b) Schwarz, F.; Koch, M.; Kastlunger, G.; Berke, H.; Stadler, R.; Venkatesan, K.; Lortscher, E. Angew. Chem. Int. Ed. 2016, 55, 11781.
  (c) Yang, G.; Sara, S.; Liu, Z.; Li, X.; Hatef, S.; Tan, Z.; Li, R.; Zheng, J.; Dong, X.; Liu, J.; Yang, Y.; Shi, J.; Xiao, Z; Zhang, G.; Colin, L.; Hong, W.; Zhang, D. Chem. Sci. 2017, 8, 7505.
  (d) Cai, S.; Deng, W.; Huang, F.; Chen, L.; Tang, C.; He, W.; Long, S.; Li, R.; Tan, Z.; Liu, J.; Xiao, Z.; Zhang, D.; Hong, W. Angew. Chem. Int. Ed. 2019, 58, 1.
  (e) Huang, C.; Jevric, M.; Borges, A.; Olsen, S. T.; Hamill, J. M.; Zheng, J.-T.; Yang, Y.; Rudnev, A.; Baghernejad, M.; Broekmann, P.; Petersen, A. U.; Wandlowski, T.; Mikkelsen, K. V.; Solomon, G. C.; Brøndsted Nielsen, M.; Hong, W. Nat. Commun. 2017, 8, 15436.
6. [6]
  Puodziukynaite, E.; Wang, H. W.; Lawrence, J.; Wise, A. J.; Rus-sell, T. P.; Barnes, M. D.; Emrick, T. J. Am. Chem. Soc. 2014, 136, 11043. doi: 10.1021/ja504670k
7. [7]
  Zhou, Y.; Zhuang, Y.; Li, X.; Hans, A.; Yu, L.; Ding, J.; Zhu, L. Chem. Eur. J. 2017, 23, 7642. doi: 10.1002/chem.201700947
8. [8]
  (a) Wang, X.; Ng, J. K.-P.; Jia, P.; Lin, T.; Cho, C. M.; Xu, J.; Lu, X.; He, C. Macromolecules 2009, 42, 5534.
  (b) Tsurui, K.; Murai, M.; Ku, S.-Y.; Hawker, C. J.; Robb, M. J. Adv. Funct. Mater. 2014, 24, 7338.
9. [9]
  Xin, H.; Ge, C.; Fu, L.; Yang, X.; Gao, X. Chin. J. Org. Chem. 2017, 37, 711(in Chinese).
10. [10]
  Ran, H.; Duan, X.; Zheng, R.; Xie, F.; Chen, L.; Zhao, Z.; Han, R.; Lei, Z.; Hu, J. ACS Appl. Mater. Interfaces 2020, 12, 23225. doi: 10.1021/acsami.0c04552
11. [11]
  Zhai, W..; Zhou, E. Chin. J. Org. Chem. 2016, 36, 2786(in Chinese).
12. [12]
  (a) Lin, Y.; He, Q.; Zhao, F.; Huo, L.; Mai, J.; Lu, X.; Su, C.; Li, T.; Wang, Y.; Zhu, J.; Sun, Y.; Wang, C.; Zhan, X. J. Am. Chem. Soc. 2016, 138, 2973.
  (b) Cai, L. P.; Moehl, T.; Moon, S. J.; Decoppet, J. D.; Robin, H. B.; Xue, Z. S.; Liu, B.; Zakeeruddin, S. M.; Grätzel, M. Org. Lett. 2014, 16, 106.
13. [13]
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