Citation: Hou Bin, Li Jing, Xin Hanshen, Yang Xiaodi, Gao Honglei, Peng Peizhen, Gao Xike. Design, Synthesis and Field Effect Characteristics of Diazulene Diimides Bridged by Aromatic Group[J]. Acta Chimica Sinica, ;2020, 78(8): 788-796. doi: 10.6023/A20050161 shu

Design, Synthesis and Field Effect Characteristics of Diazulene Diimides Bridged by Aromatic Group

Hou Bin ^a ,
Li Jing ^a ,
Xin Hanshen ^a ,
Yang Xiaodi ^b,, ,
Gao Honglei ^a,, ,
Peng Peizhen ^a ,
Gao Xike ^a

a.
Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China
b.
Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China

Corresponding author: Yang Xiaodi, yangxiaodi@shutcm.edu.cn; gaoxk@mail.sioc.ac.cn Gao Honglei, gaoxk@mail.sioc.ac.cn
Received Date: 11 May 2020
Available Online: 10 June 2020
Fund Project: the Science and Technology Commission of Shanghai Municipality 18JC1410600the Science and Technology Commission of Shanghai Municipality 19XD1424700Project 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 National Natural Science Foundation of China 21522209

Figures(6)

Azulene, a bicyclic nonbenzenoid aromatic hydrocarbon, shows completely different physicochemical properties compared with its isomeric naphthalene. Herein, we made use of the diverse reactivity of each position on azulene to design a new synthetic strategy for azulene-based diimides bridged by phenyl or thieno[3, 2-b]thiophenyl group, 2-(azulen-2'-yl)-5-(azulen-2''-yl)benzene-1, 1':4, 1''-tetracarboxylic diimides (AzAzBDI-1/2) and 2-(azulen-2'-yl)-5- (azulen-2''-yl)thieno[3, 2-b]thiophene-3, 1':6, 1''-tetracarboxylic diimide (AzAzTTDI). The key step was double trifluoroacetylation at 1-position of two azulene moieties of the molecule followed by hydrolysis, anhydridization and imidization to obtain the target compounds. The single crystal structure analysis demonstrates that AzAzBDI-2 has twisted molecular backbone. The adjacent two molecules form a dimer through the intermolecular π-π stacking (0.365 nm) between the five-membered ring and the seven-membered ring of two different azulene units. Strong π-π intermolecular interactions (0.355 nm) exist among the dimers to form a slipped one-dimensional (1D) packing motif in the crystal. For three compounds, the optoelectronic properties were investigated by UV-vis absorption spectra and cyclic voltammetry, and their energy levels of highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) and the energy gaps were calculated. The HOMO/LUMO energy levels of AzAzBDI-1, AzAzBDI-2 and AzAzTTDI are －5.56/－3.28 eV, －5.56/ －3.30 eV and －5.57/－3.42 eV, respectively. The end absorptions of AzAzBDI-1, AzAzBDI-2 and AzAzTTDI in thin films show obvious red-shift (13, 13 and 25 nm) relative to those in CHCl₃ solution, indicating strong intermolecular interactions in solid state. The charge carrier transport properties of three compounds were studied through organic field-effect transistors (OFETs). Bottom-gate and top-contact OFET devices of AzAzBDI-1, AzAzBDI-2 and AzAzTTDI were fabricated by spin-coated their respective solution on octadecyltrimethoxysilane (OTMS)-treated SiO₂/Si substrates. Under nitrogen atmosphere, all of these three compounds displayed electron-dominated ambipolar organic semiconductor characteristics. The electron mobilities of AzAzBDI-1 and AzAzBDI-2 were 0.068 cm²·V^－1·s^－1 and 0.086 cm²·V^－1·s^－1 and the hole mobility were 3.1×10^－4 cm²·V^－1·s^－1 and 1.5×10^－3 cm²·V^－1·s^－1, respectively. OFETs based on AzAzTTDI showed the highest electron mobility and hole mobilities of 0.087 cm²·V^－1·s^－1 and 8.8×10^－3 cm²·V^－1·s^－1, respectively. The X-ray diffraction (XRD) and atomic force microscopy (AFM) studies demonstrate thin films of AzAzBDI-1, AzAzBDI-2 and AzAzTTDI show better crystallinity and form larger size of microstructures by annealing, which is consistent with the enhanced device performance after thermal annealing.
- azulene,
- nonbenzenoid aromatic hydrocarbon,
- imides,
- organic field-effect transistors,
- organic semiconductor
1. [1]
  (a) Wheland, G. W.; Mann, D. E. J. Chem. Phys. 1949, 17, 264. (b) Anderson, A. G.; Steckler, B. M. J. Am. Chem. Soc. 1959, 81, 4941.
2. [2]
  Michl, J.; Thulstrup, E. W. Tetrahedron 1976, 32, 205. doi: 10.1016/0040-4020(76)87002-0
3. [3]
  Beer, M.; Longuet-Higgins, H. C. J. Chem. Phys. 1955, 23, 1390. doi: 10.1063/1.1742314
4. [4]
  Kasha, M. Faraday Soc. 1950, 9, 14. doi: 10.1039/df9500900014
5. [5]
6. [6]
7. [7]
  (a) Umeyama, T.; Watanabe, Y.; Miyata, T.; Imahori, H. Chem. Lett. 2015, 44, 47. (b) Chen, Y.; Zhu, Y.; Yang, D.; Zhao, S.; Zhang, L.; Yang, L.; Wu, J.; Huang, Y.; Xu, Z.; Lu, Z. Chem. Eur. J. 2016, 22, 14527. (c) Puodziukynaite, E.; Wang, H. W.; Lawrence, J.; Wise, A. J.; Russell, T. P.; Barnes, M. D.; Emrick, T. J. Am. Chem. Soc. 2014, 136, 11043.
8. [8]
  (a) Nishimura, H.; Ishida, N.; Shimazaki, A.; Wakamiya, A.; Saeki, A.; Scott, L. T.; Murata, Y. J. Am. Chem. Soc. 2015, 137, 15656. (b) Truong, M. A.; Lee, J.; Nakamura, T.; Seo, J. Y.; Jung, M.; Ozaki, M.; Shimazaki, A.; Shioya, N.; Hasegawa, T.; Murata, Y.; Zakeeruddin, S. M.; Grätzel, M.; Murdey, R.; Wakamiya, A. Chem. Eur. J. 2019, 25, 6741.
9. [9]
  (a) Asato, A. E.; Liu, R. S. H.; Rao, V. P.; Cai, Y. M. Tetrahedron Lett. 1996, 37, 419. (b) Iftime, G.; Lacroix, P. G.; Nakatani, K.; Razus, A. C. Tetrahedron Lett. 1998, 39, 6853. (c) Lacroix, P. G.; Malfant, I.; Iftime, G.; Razus, A. C.; Nakatani, K.; Delaire, J. A. Chem. Eur. J. 2000, 6, 2599. (d) Coe, B. J.; Harris, J. A.; Asselberghs, I.; Clays, K.; Olbrechts, G.; Persoons, A.; Hupp, J. T.; Johnson, R. C.; Coles, S. J.; Hursthouse, M. B.; Nakatani, K. Adv. Funct. Mater. 2002, 12, 110. (e) Cristian, L.; Sasaki, I.; Lacroix, P. G.; Donnadieu, B.; Asselberghs, I.; Clays, K.; Razus, A. C. Chem. Mater. 2004, 16, 3543. (f) Migalska-Zalas, A.; El kouari, Y.; Touhtouh, S. Opt. Mater. 2012, 34, 1639. (g) Herrmann, R.; Pedersen, B.; Wagner, G.; Youn, J.-H. J. Organomet. Chem. 1998, 571, 261.
10. [10]
  (a) Kurotobi, K.; Kim, K. S.; Noh, S. B.; Kim, D.; Osuka, A. Angew. Chem., Int. Ed. 2006, 45, 3944. (b) Wang, F. K.; Lin, T. T.; He, C. B.; Chi, H.; Tang, T.; Lai, Y. H. J. Mater. Chem. 2012, 22, 10448. (c) Ince, M.; Bartelmess, J.; Kiessling, D.; Dirian, K.; Martinez-Diaz, M. V.; Torres, T.; Guldi, D. M. Chem. Sci. 2012, 3, 1472.
11. [11]
  (a) Ito, S.; Morita, N. Eur. J. Org. Chem. 2009, 4567. (b) Dong, J.; Zhang, H. Chin. Chem. Lett. 2016, 27, 1097. (c) Xin, H.; Gao, X. ChemPlusChem 2017, 82, 945. (d) Ou, L.; Zhou, Y.; Wu, B.; Zhu, L. Chin. Chem. Lett. 2019, 30, 1903.
12. [12]
  Lemal, D. M.; Goldman, G. D. J. Chem. Educ. 1988, 65, 923. doi: 10.1021/ed065p923
13. [13]
  Horowitz, G.; Kouki, F.; Spearman, P.; Fichou, D.; Nogues, C.; Pan, X.; Garnier, F. Adv. Mater. 1996, 8, 242. doi: 10.1002/adma.19960080312
14. [14]
15. [15]
16. [16]
  Guo, X.; Facchetti, A.; Marks, T. J. Chem. Rev. 2014, 114, 8943. doi: 10.1021/cr500225d
17. [17]
  Xin, H.; Ge, C.; Yang, X.; Gao, H.; Yang, X.; Gao, X. Chem. Sci. 2016, 7, 6701. doi: 10.1039/C6SC02504H
18. [18]
  (a) Xin, H.; Li, J.; Ge, C.; Yang, X.; Xue, T.; Gao, X. Mater. Chem. Front. 2018, 2, 975. (b) Xin, H.; Ge, C.; Jiao, X.; Yang, X.; Rundel, K.; McNeill, C. R.; Gao, X. Angew. Chem., Int. Ed. 2018, 57, 1322.
19. [19]
  Gao, H.; Yang, X.; Xin, H.; Gao, T.; Gong, H.; Gao, X. Chin. J. Org. Chem. 2018, 38, 2680 (in Chinese).
20. [20]
  Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Petersson, G. A.; Nakatsuji, H.; Li, X.; Caricato, M.; Marenich, A. V.; Bloino, J.; Janesko, B. G.; Gomperts, R.; Mennucci, B.; Hratchian, H. P.; Ortiz, J. V.; Izmaylov, A. F.; Sonnenberg, J. L.; Williams-Young, D.; Ding, F.; Lipparini, F.; Egidi, F.; Goings, J.; Peng, B.; Petrone, A.; Henderson, T.; Ranasinghe, D.; Zakrzewski, V. G.; Gao, J.; Rega, N.; Zheng, G.; Liang, W.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Throssell, K.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M. J.; Heyd, J. J.; Brothers, E. N.; Kudin, K. N.; Staroverov, V. N.; Keith, T. A.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A. P.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Millam, J. M.; Klene, M.; Adamo, C.; Cammi, R.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Farkas, O.; Foresman, J. B.; Fox, D. J. Gaussian 16, Gaussian, Inc., Wallingford CT, 2016.
21. [21]
  Brown, A. R.; Jarrett, C. P.; deLeeuw, D. M.; Matters, M. Synth. Met. 1997, 88, 37. doi: 10.1016/S0379-6779(97)80881-8
22. [22]
  (a) Lei, T.; Dou, J.; Pei, J. Adv. Mater. 2012, 24, 6457. (b) Zhang, F.; Hu, Y.; Schuettfort, T.; Di, C. A.; Gao, X.; McNeill, C. R.; Thomsen, L. S.; Mannsfeld, C.; Yuan, W.; Sirringhaus, H.; Zhu, D. J. Am. Chem. Soc. 2013, 135, 2338.
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