Citation: Bin Hou, Jing Li, Xiaodi Yang, Jianwei Zhang, Hanshen Xin, Congwu Ge, Xike Gao. Azulenoisoindigo: A building block for π-functional materials with reversible redox behavior and proton responsiveness[J]. Chinese Chemical Letters, ;2022, 33(4): 2147-2150. doi: 10.1016/j.cclet.2021.08.079 shu

Azulenoisoindigo: A building block for π-functional materials with reversible redox behavior and proton responsiveness

Bin Hou ^a ,
Jing Li ^a ,
Xiaodi Yang ^b ,
Jianwei Zhang ^b ,
Hanshen Xin ^a ,
Congwu Ge ^a ,
Xike Gao ^{a, *,}

a.
Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China
b.
Experiment Center for Science and Technology, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China

gaoxk@mail.sioc.ac.cn

Received Date: 26 July 2021
Revised Date: 11 August 2021
Accepted Date: 18 August 2021
Available Online: 21 August 2021

Figures(7)

Azulene, one of representative nonbenzenoid aromatic hydrocarbons, exhibits unique molecular structure and distinctive physical and chemical properties. Herein, azulenoisoindigo (AzII), an azulene-based isoindigo analogue, is designed and synthesized, which has a twisted molecular backbone and R/S-isomers in single crystals. Interestingly, AzII shows the characteristics of both isoindigo and azulene, such as reversible redox behavior and reversible proton responsiveness. UV-vis-NIR, ¹H NMR and electron paramagnetic resonance (EPR) measurements were carried out to get insights into the possible mechanism of the proton-responsive property of AzII. The results demonstrated that only one azulenyl moiety of molecule of AzII was protonated and deprotonated, and the protonated AzII can be further oxidized to form azulenium cation radicals.
- Azulene,
- Nonbenzenoid aromatic hydrocarbons,
- Isoindigo,
- π-Functional materials,
- Proton responsiveness
1. [1]
  A.G. Anderson, B.M. Steckler, J. Am. Chem. Soc. 81(1959) 4941-4946. doi: 10.1021/ja01527a046
2. [2]
  J. Michl, E.W. Thulstrup, Tetrahedron 32(1976) 205-209. doi: 10.1016/0040-4020(76)87002-0
3. [3]
  J. Dong, H. Zhang, Chin. Chem. Lett. 27(2016) 1097-1104. doi: 10.1016/j.cclet.2016.05.005
4. [4]
  S. Ito, N. Morita, Eur. J. Org. Chem. (2009) 4567-4579.
5. [5]
  L. Ou, Y. Zhou, B. Wu, L. Zhu, Chin. Chem. Lett. 30(2019) 1903-1907. doi: 10.1016/j.cclet.2019.08.015
6. [6]
  H. Xin, X. Gao, ChemPlusChem 82(2017) 945-956. doi: 10.1002/cplu.201700039
7. [7]
  H. Xin, B. Hou, X. Gao, Acc. Chem. Res. 54(2021) 1737-1753. doi: 10.1021/acs.accounts.0c00893
8. [8]
  N. He, R.E. Gyurcsanyi, T. Lindfors, Analyst 141(2016) 2990-2997. doi: 10.1039/C5AN02664D
9. [9]
  N. He, L. Hoefler, R. Latonen, T. Lindfors, Sens. Actuators B 207(2015) 918-925. doi: 10.1016/j.snb.2014.10.048
10. [10]
  T. Tang, T. Lin, F. Wang, C. He, Polym. Chem. 5(2014) 2980-2989. doi: 10.1039/C3PY01609A
11. [11]
  F. Wang, T.T. Lin, C. He, et al., J. Mater. Chem. 22(2012) 10448-10451. doi: 10.1039/c2jm31098h
12. [12]
  Y. Yamaguchi, K. Ogawa, K. Nakayama, Y. Ohba, H. Katagiri, J. Am. Chem. Soc. 135(2013) 19095-19098. doi: 10.1021/ja410696j
13. [13]
  Y. Yamaguchi, M. Takubo, K. Ogawa, et al., J. Am. Chem. Soc. 138(2016) 11335-11343. doi: 10.1021/jacs.6b06877
14. [14]
  H. Nishimura, N. Ishida, A. Shimazaki, et al., J. Am. Chem. Soc. 137(2015) 15656-15659. doi: 10.1021/jacs.5b11008
15. [15]
  T. Umeyama, Y. Watanabe, T. Miyata, H. Imahori, Chem. Lett. 44(2015) 47-49. doi: 10.1246/cl.140904
16. [16]
  J. Yao, Z. Cai, Z. Liu, et al., Macromolecules 48(2015) 2039-2047. doi: 10.1021/acs.macromol.5b00158
17. [17]
  E. Amir, R.J. Amir, L.M. Campos, C.J. Hawker, J. Am. Chem. Soc. 133(2011) 10046-10049. doi: 10.1021/ja203267g
18. [18]
  E. Amir, M. Murai, R.J. Amir, et al., Chem. Sci. 5(2014) 4483-4489. doi: 10.1039/C4SC02210F
19. [19]
  M. Murai, E. Amir, R.J. Amir, C.J. Hawker, Chem. Sci. 3(2012) 2721-2725. doi: 10.1039/c2sc20615c
20. [20]
  M. Murai, S.Y. Ku, N.D. Treat, et al., Chem. Sci. 5(2014) 3753-3760. doi: 10.1039/C4SC01623H
21. [21]
  K. Tsurui, M. Murai, S.Y. Ku, C.J. Hawker, M.J. Robb, Adv. Funct. Mater. 24(2014) 7338-7347. doi: 10.1002/adfm.201402554
22. [22]
  X.K. Wee, W.K. Yeo, B. Zhang, et al., Bioorg. Med. Chem. 17(2009) 7562-7571. doi: 10.1016/j.bmc.2009.09.008
23. [23]
  Z. Xiao, Y. Wang, L. Lu, et al., Leuk. Res. 30(2006) 54-59. doi: 10.1016/j.leukres.2005.05.012
24. [24]
  X. Guo, A. Facchetti, T.J. Marks, Chem. Rev. 114(2014) 8943-9021. doi: 10.1021/cr500225d
25. [25]
  T. Lei, J. Wang, J. Pei, Acc. Chem. Res. 47(2014) 1117-1126. doi: 10.1021/ar400254j
26. [26]
  J. Li, J. Cao, L. Duan, H. Zhang, Asian J. Org. Chem. 7(2018) 2147-2160. doi: 10.1002/ajoc.201800198
27. [27]
  J. Mei, K.R. Graham, R. Stalder, J.R. Reynolds, Org. Lett. 12(2010) 660-663. doi: 10.1021/ol902512x
28. [28]
  T. Lei, Y. Cao, Y. Fan, et al., J. Am. Chem. Soc. 133(2011) 6099-6101. doi: 10.1021/ja111066r
29. [29]
  R. Stalder, J. Mei, J.R. Reynolds, Macromolecules 43(2010) 8348-8352. doi: 10.1021/ma1018445
30. [30]
  R.S. Ashraf, A.J. Kronemeijer, D.I. James, H. Sirringhaus, I. McCulloch, Chem. Commun. 48(2012) 3939-3941. doi: 10.1039/c2cc30169e
31. [31]
  G. de Miguel, L. Camacho, E.M. García-Frutos, J. Mater. Chem. C 4(2016) 1208-1214.
32. [32]
  J. Huang, Z. Mao, Z. Chen, et al., Chem. Mater. 28(2016) 2209-2218. doi: 10.1021/acs.chemmater.6b00154
33. [33]
  Y. Lu, Y. Liu, Y. Dai, et al., Chem. Asian J. 12(2017) 302-307. doi: 10.1002/asia.201601671
34. [34]
  C. Li, H. -I. Un, J. Peng, et al., Chem. Eur. J. 24(2018) 9807-9811. doi: 10.1002/chem.201801432
35. [35]
  C. Li, H. Zhang, S. Mirie, et al., Org. Chem. Front. 5(2018) 442-446. doi: 10.1039/C7QO00841D
36. [36]
  H. Gao, C. Ge, B. Hou, H. Xin, X. Gao, ACS Macro Lett 8(2019) 1360-1364. doi: 10.1021/acsmacrolett.9b00657
37. [37]
  B. Hou, J. Li, H. Xin, et al., Acta Chim. Sinica 78(2021) 788-796.
38. [38]
  H. Xin, C. Ge, X. Jiao, et al., Angew. Chem. Int. Ed. 57(2018) 1322-1326. doi: 10.1002/anie.201711802
39. [39]
  H. Xin, C. Ge, X. Yang, et al., Chem. Sci. 7(2016) 6701-6705. doi: 10.1039/C6SC02504H
40. [40]
  H. Xin, J. Li, R. -Q. Lu, X. Gao, T.M. Swager, J. Am. Chem. Soc. 142(2020) 13598-13605. doi: 10.1021/jacs.0c06299
41. [41]
  N. Tetsuo, S. Shuichi, M. Shingo, Bull. Chem. Soc. Jpn. 35(1962) 1990-1998. doi: 10.1246/bcsj.35.1990
42. [42]
  L. Shi, Y. Guo, W. Hu, Y. Liu, Mater. Chem. Front. 1(2017) 2423-2456. doi: 10.1039/C7QM00169J
43. [43]
  C. Kogawa, A. Fujiwara, R. Sekiguchi, et al., Tetrahedron 74(2018) 7018-7029. doi: 10.1016/j.tet.2018.10.020
44. [44]
  T. Hasegawa, M. Ashizawa, H. Matsumoto, RSC Adv. 5(2015) 61035-61043. doi: 10.1039/C5RA07660A
45. [45]
  Y.K. Voronina, D.B. Krivolapov, A.V. Bogdanov, V.F. Mironov, I.A. Litvinov, J. Struct. Chem. 53(2012) 413-416. doi: 10.1134/S0022476612020321
46. [46]
  A.R. Brown, C.P. Jarrett, D.M. de Leeuw, M. Matters, Synth. Met. 88(1997) 37-55. doi: 10.1016/S0379-6779(97)80881-8
47. [47]
  B. Hou, J. Li, X. Yang, et al., ChemRxiv (2021), doi:10.26434/chemrxiv.14092937.v1. doi: 10.26434/chemrxiv.14092937.v1
1. [1]
  Bo Yu , Pengchen Du , Jianwen Guo , Hanshen Xin , Jianhua Zhang . Nonalternant isomer of pentacene fusing two azulene units. Chinese Chemical Letters, 2024, 35(5): 109321-. doi: 10.1016/j.cclet.2023.109321
2. [2]
  Tingting Huang , Zhuanlong Ding , Hao Liu , Ping-An Chen , Longfeng Zhao , Yuanyuan Hu , Yifan Yao , Kun Yang , Zebing Zeng . Electron-transporting boron-doped polycyclic aromatic hydrocarbons: Facile synthesis and heteroatom doping positions-modulated optoelectronic properties. Chinese Chemical Letters, 2024, 35(4): 109117-. doi: 10.1016/j.cclet.2023.109117
3. [3]
  Xinyu Ren , Hong Liu , Jingang Wang , Jiayuan Yu . Electrospinning-derived functional carbon-based materials for energy conversion and storage. Chinese Chemical Letters, 2024, 35(6): 109282-. doi: 10.1016/j.cclet.2023.109282
4. [4]
  Yunfa Dong , Shijie Zhong , Yuhui He , Zhezhi Liu , Shengyu Zhou , Qun Li , Yashuai Pang , Haodong Xie , Yuanpeng Ji , Yuanpeng Liu , Jiecai Han , Weidong He . Modification strategies for non-aqueous, highly proton-conductive benzimidazole-based high-temperature proton exchange membranes. Chinese Chemical Letters, 2024, 35(4): 109261-. doi: 10.1016/j.cclet.2023.109261
5. [5]
  Jiaqi Lin , Pupu Yang , Yimin Jiang , Shiqian Du , Dongcai Zhang , Gen Huang , Jinbo Wang , Jun Wang , Qie Liu , Miaoyu Li , Yujie Wu , Peng Long , Yangyang Zhou , Li Tao , Shuangyin Wang . Surface decoration prompting the decontamination of active sites in high-temperature proton exchange membrane fuel cells. Chinese Chemical Letters, 2024, 35(11): 109435-. doi: 10.1016/j.cclet.2023.109435
6. [6]
  Jingyuan Yang , Xinyu Tian , Liuzhong Yuan , Yu Liu , Yue Wang , Chuandong Dou . Enhancing stability of diradical polycyclic hydrocarbons via P=O-attaching. Chinese Chemical Letters, 2024, 35(8): 109745-. doi: 10.1016/j.cclet.2024.109745
7. [7]
  Uttam Pandurang Patil . Porous carbon catalysis in sustainable synthesis of functional heterocycles: An overview. Chinese Chemical Letters, 2024, 35(8): 109472-. doi: 10.1016/j.cclet.2023.109472
8. [8]
  Qinghong Zhang , Qiao Zhao , Xiaodi Wu , Li Wang , Kairui Shen , Yuchen Hua , Cheng Gao , Yu Zhang , Mei Peng , Kai Zhao . Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer. Chinese Chemical Letters, 2025, 36(2): 110167-. doi: 10.1016/j.cclet.2024.110167
9. [9]
  Shaohua Zhang , Liyao Liu , Yingqiao Ma , Chong-an Di . Advances in theoretical calculations of organic thermoelectric materials. Chinese Chemical Letters, 2024, 35(8): 109749-. doi: 10.1016/j.cclet.2024.109749
10. [10]
  Junjie Wang , Yan Wang , Zhengdong Li , Changqiang Xie , Musammir Khan , Xingzhou Peng , Fabiao Yu . Triphenylamine-AIEgens photoactive materials for cancer theranostics. Chinese Chemical Letters, 2024, 35(6): 108934-. doi: 10.1016/j.cclet.2023.108934
11. [11]
  Aolei Tan , Xiaoxiao Ma . Exploring the functional roles of small-molecule metabolites in disease research: Recent advancements in metabolomics. Chinese Chemical Letters, 2024, 35(8): 109276-. doi: 10.1016/j.cclet.2023.109276
12. [12]
  Tianze Wang , Junyi Ren , Dongxiang Zhang , Huan Wang , Jianjun Du , Xin-Dong Jiang , Guiling Wang . Development of functional dye with redshifted absorption based on Knoevenagel condensation at 1-site in phenyl[b]-fused BODIPY. Chinese Chemical Letters, 2024, 35(6): 108862-. doi: 10.1016/j.cclet.2023.108862
13. [13]
  Guiyang Zheng , Xuelian Kang , Haoran Ye , Wei Fan , Christian Sonne , Su Shiung Lam , Rock Keey Liew , Changlei Xia , Yang Shi , Shengbo Ge . Recent advances in functional utilisation of environmentally friendly and recyclable high-performance green biocomposites: A review. Chinese Chemical Letters, 2024, 35(4): 108817-. doi: 10.1016/j.cclet.2023.108817
14. [14]
  Zeyu Jiang , Yadi Wang , Changwei Chen , Chi He . Progress and challenge of functional single-atom catalysts for the catalytic oxidation of volatile organic compounds. Chinese Chemical Letters, 2024, 35(9): 109400-. doi: 10.1016/j.cclet.2023.109400
15. [15]
  Jiajing Wu , Ru-Ling Tang , Sheng-Ping Guo . Three types of promising functional building units for designing metal halide nonlinear optical crystals. Chinese Journal of Structural Chemistry, 2024, 43(6): 100291-100291. doi: 10.1016/j.cjsc.2024.100291
16. [16]
  Xin Li , Wanting Fu , Ruiqing Guan , Yue Yuan , Qinmei Zhong , Gang Yao , Sheng-Tao Yang , Liandong Jing , Song Bai . Nucleophiles promotes the decomposition of electrophilic functional groups of tetracycline in ZVI/H₂O₂ system: Efficiency and mechanism. Chinese Chemical Letters, 2024, 35(10): 109625-. doi: 10.1016/j.cclet.2024.109625
17. [17]
  Lilin Song , Mengru Sun , Yuqing Song , Feng Zhang , Bei Zhao , Hairong Zeng , Jinhui Shi , Huixin Liu , Shanshan Zhao , Tian Tian , Heng Yin , Guangbo Ge . Rationally engineered IR-783 octanoate as an enzyme-activatable fluorogenic tool for functional imaging of hNotum in living systems. Chinese Chemical Letters, 2024, 35(11): 109601-. doi: 10.1016/j.cclet.2024.109601
18. [18]
  Rui PAN , Yuting MENG , Ruigang XIE , Daixiang CHEN , Jiefa SHEN , Shenghu YAN , Jianwu LIU , Yue ZHANG . Selective electrocatalytic reduction of Sn(Ⅳ) by carbon nitrogen materials prepared with different precursors. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 1015-1024. doi: 10.11862/CJIC.20230433
19. [19]
  Chao Ma , Cong Lin , Jian Li . MicroED as a powerful technique for the structure determination of complex porous materials. Chinese Journal of Structural Chemistry, 2024, 43(3): 100209-100209. doi: 10.1016/j.cjsc.2023.100209
20. [20]
  Yuhan Wu , Qing Zhao , Zhijie Wang . Layered vanadium oxides: Promising cathode materials for calcium-ion batteries. Chinese Journal of Structural Chemistry, 2024, 43(5): 100271-100271. doi: 10.1016/j.cjsc.2024.100271

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(569)
HTML views(75)

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