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]
1. [1]
  Mengfei He , Chao Chen , Yue Tang , Si Meng , Zunfa Wang , Liyu Wang , Jiabao Xing , Xinyu Zhang , Jiahui Huang , Jiangbo Lu , Hongmei Jing , Xiangyu Liu , Hua Xu . Epitaxial Growth of Nonlayered 2D MnTe Nanosheets with Thickness-Tunable Conduction for p-Type Field Effect Transistor and Superior Contact Electrode. Acta Physico-Chimica Sinica, 2025, 41(2): 100016-. doi: 10.3866/PKU.WHXB202310029
2. [2]
  Renqing Lü , Shutao Wang , Fang Wang , Guoping Shen . Computational Chemistry Aided Organic Chemistry Teaching: A Case of Comparison of Basicity and Stability of Diazine Isomers. University Chemistry, 2025, 40(3): 76-82. doi: 10.12461/PKU.DXHX202404119
3. [3]
  Xiaolei Jiang , Fangdong Hu . Exploring the Mirror World in Organic Chemistry: the Teaching Design of “Enantiomers” from the Perspective of Curriculum and Ideological Education. University Chemistry, 2024, 39(10): 174-181. doi: 10.3866/PKU.DXHX202402052
4. [4]
  Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
5. [5]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
6. [6]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
7. [7]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
8. [8]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
9. [9]
  Min LIU , Huapeng RUAN , Zhongtao FENG , Xue DONG , Haiyan CUI , Xinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362
10. [10]
  Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139
11. [11]
  Ran HUO , Zhaohui ZHANG , Xi SU , Long CHEN . Research progress on multivariate two dimensional conjugated metal organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2063-2074. doi: 10.11862/CJIC.20240195
12. [12]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
13. [13]
  Xingyuan Lu , Yutao Yao , Junjing Gu , Peifeng Su . Energy Decomposition Analysis and Its Application in the Many-Body Effect of Water Clusters. University Chemistry, 2025, 40(3): 100-107. doi: 10.12461/PKU.DXHX202405074
14. [14]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
15. [15]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
16. [16]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
17. [17]
  Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
18. [18]
  Yongzhi LI , Han ZHANG , Gangding WANG , Yanwei SUI , Lei HOU , Yaoyu WANG . A two-dimensional metal-organic framework for the determination of nitrofurantoin and nitrofurazone in aqueous solution. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 245-253. doi: 10.11862/CJIC.20240307
19. [19]
  Shiyang He , Dandan Chu , Zhixin Pang , Yuhang Du , Jiayi Wang , Yuhong Chen , Yumeng Su , Jianhua Qin , Xiangrong Pan , Zhan Zhou , Jingguo Li , Lufang Ma , Chaoliang Tan . 铂单原子功能化的二维Al-TCPP金属-有机框架纳米片用于增强光动力抗菌治疗. Acta Physico-Chimica Sinica, 2025, 41(5): 100046-. doi: 10.1016/j.actphy.2025.100046
20. [20]
  Xinxin YU , Yongxing LIU , Xiaohong YI , Miao CHANG , Fei WANG , Peng WANG , Chongchen WANG . Photocatalytic peroxydisulfate activation for degrading organic pollutants over the zero-valent iron recovered from subway tunnels. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 864-876. doi: 10.11862/CJIC.20240438

Get Citation

PDF

XML

Metrics

PDF Downloads(12)
Abstract views(4321)
HTML views(561)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142