Citation: Liu Jihong, Jin Kun, Tian Zhenhao, Luo Gen. Naphthalene Benzimidazole Derivatives: Syntheses and Structure Confirmations[J]. Chemistry, ;2020, 83(1): 64-69. shu

Naphthalene Benzimidazole Derivatives: Syntheses and Structure Confirmations

Liu Jihong ^1, ,
Jin Kun ² ,
Tian Zhenhao ² ,
Luo Gen ¹

1.
Institute of Chemical Technology, Dalian University of technology, Dalian, 116024
2.
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116024

Received Date: 16 August 2019
Accepted Date: 15 October 2019

Figures(8)

The naphthalene benzimidazole (NBI) with 1 and 4 monosubstituted derivatives 1~4 were synthesized and purified. The structure of compound 1 was analyzed in detail by using UV-Vis, IR, MS, ¹H NMR, ¹³C NMR, DEPT, ¹H-¹³C HSQC, ¹H-¹³C HMBC techniques, and the positions of ¹H and ¹³C NMR peaks of the derivatives were assigned. Quantum calculations were also applied by GIAO and CSGT methods to calculate the NMR shifts of NBI derivatives. The structure of the compounds were confirmed by various spectral techniques.
- Naphthalene benzimidazoles,
- Liquid NMR,
- 2D NMR,
- Quantization,
- Structure confirmation
1. [1]
  Wojciechowski K. Dyes Pigments,1997, 33(2):149~165.
2. [2]
  Khosravi A, Moradian S, Gharanjig K, et al. Dyes Pigments, 2006, 69(1-2):79~92.
3. [3]
  Bojinov V, Grabchev I. Dyes Pigments, 2001, 51(1):57~61.
4. [4]
5. [5]
  Li X L, Lin Y J, Yuan Y K, et al. Tetrahedron, 2011, 67(12):2299~2304.
6. [6]
  Chen Z, Liang X, Zhang H Y, et al. J. Med. Chem., 2010, 53(6):2589~2600.
7. [7]
  Yang Q, Yang P, Qian X H, et al. Bioorg. Med. Chem. Lett., 2008, 18(23):6210~6213.
8. [8]
  Zhang W, Chen M, Wu Y L, et al. Sci. Rep., 2015, 5:13693.
9. [9]
  Xie L J, Cui J N, Qian X H, et al. Bioorg. Med. Chem., 2011, 19(2):961~967.
10. [10]
  Yin H, Zhu W P, Xu Y F, et al. Eur. J. Med. Chem., 2011, 46(7):3030~3037.
11. [11]
  Jia H M, Xia S H, Feng H, et al. Org Biomol. Chem., 2018, 16(12):2074~2082.
12. [12]
  Dai Z R, Ge G B, Feng L, et al. J. Am. Chem. Soc., 2015, 137(45):14488~14495.
13. [13]
  Tang Y H, Kong X Q, Xu A, et al. Angew. Chem. Int. Ed., 2016, 55(10):3356~3359.
14. [14]
  Li B, Yu Y L, Xiang F Q, et al. ACS Appl. Mater. Interf., 2018, 10(19):16282~16290.
15. [15]
  Xing P F, Feng Y X, Niu Y M, et al. Chem. Eur. J., 2018, 24(22):5748~5753.
16. [16]
  Yang G X, Zhang J, Zhu S J, et al. Sens. Actuat. B., 2018, 261:51~57.
17. [17]
  Zhang Z, Fan J L, Zhao Y H, et al. ACS Sensors, 2018, 3(3):735~741.
18. [18]
  Jin Q, Feng L, Wang D D, et al. ACS Appl. Mater. Interf., 2015, 7(51):28474~28481.
19. [19]
  Dai Z R, Feng L, Jin Q, et al. Chem. Sci., 2017, 8(4):2795~2803.
20. [20]
21. [21]
  Do T T, Takeda Y, Manzhos S, et al. J. Mater. Chem. C, 2018, 6(14):3774~3786.
22. [22]
  Kolosov D, Adamovich V, Djurovich P, et al. J. Am. Chem. Soc., 2002, 124(33):9945~9954.
23. [23]
  Tu G L, Mei C Y, Zhou Q G, et al. Adv. Funct. Mater., 2006, 16(1):101~106.
24. [24]
  Liu J, Zhou Q G, Cheng Y X, et al. Adv. Funct. Mater., 2006, 16(7):957~965.
25. [25]
  Mamada M, Perez-Bolivar C, Anzenbacher P. Org. Lett., 2011, 13(18):4882~4885.
26. [26]
  Mamada M, Perez-Bolivar C, Kumaki D, et al. Chem. Eur. J., 2014, 20(37):11835~11846.
27. [27]
  Jiang W, Tang J, Qi Q, et al. Dyes Pigments, 2009, 80(3):279~286.
28. [28]
  Xiao P, Dumur F, Graff B, et al. Macromolecules, 2014, 47(3):973~978.
1. [1]
  Yuan ZHU , Xiaoda ZHANG , Shasha WANG , Peng WEI , Tao YI . Conditionally restricted fluorescent probe for Fe³⁺ and Cu²⁺ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232
2. [2]
  Jiatong Hu , Qiyi Wang , Ruiwen Tang , Jiajing Feng . Photocatalytic Journey of Perylene Diimides in a Competitive Arena. University Chemistry, 2025, 40(5): 328-333. doi: 10.12461/PKU.DXHX202407015
3. [3]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
4. [4]
  Qian Huang , Zhaowei Li , Jianing Zhao , Ao Yu . Quantum Chemical Calculations Reveal the Details Below the Experimental Phenomenon. University Chemistry, 2024, 39(3): 395-400. doi: 10.3866/PKU.DXHX202309018
5. [5]
  Jinkang Jin , Yidian Sheng , Ping Lu , Zhan Lu . Introducing a Website for Learning Nuclear Magnetic Resonance (NMR) Spectrum Analysis. University Chemistry, 2024, 39(11): 388-396. doi: 10.12461/PKU.DXHX202403054
6. [6]
  Haiyang Jin , Yonghai Hui , Yongfei Zhang , Lijun Gao , Yun Wang . Application and Exploration of Nuclear Magnetic Resonance Spectrometer in Undergraduate Basic Laboratory Teaching. University Chemistry, 2025, 40(3): 245-250. doi: 10.12461/PKU.DXHX202406022
7. [7]
  Haolin Zhan , Qiyuan Fang , Jiawei Liu , Xiaoqi Shi , Xinyu Chen , Yuqing Huang , Zhong Chen . Noise Reduction of Nuclear Magnetic Resonance Spectroscopy Using Lightweight Deep Neural Network. Acta Physico-Chimica Sinica, 2025, 41(2): 2310045-0. doi: 10.3866/PKU.WHXB202310045
8. [8]
  Supin Zhao , Jing Xie . Understanding the Vibrational Stark Effect of Water Molecules Using Quantum Chemistry Calculations. University Chemistry, 2025, 40(3): 178-185. doi: 10.12461/PKU.DXHX202406024
9. [9]
  Ling Fan , Meili Pang , Yeyun Zhang , Yanmei Wang , Zhenfeng Shang . Quantum Chemistry Calculation Research on the Diels-Alder Reaction of Anthracene and Maleic Anhydride: Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 133-139. doi: 10.3866/PKU.DXHX202309024
10. [10]
  Tingbo Wang , Yao Luo , Bingyan Hu , Ruiyuan Liu , Jing Miao , Huizhe Lu . Quantitative Computational Study on the Claisen Rearrangement Reaction of Allyl Phenyl Ethers: An Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(11): 278-285. doi: 10.12461/PKU.DXHX202403082
11. [11]
  Lirui Shen , Kun Liu , Ying Yang , Dongwan Li , Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035
12. [12]
  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
13. [13]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
14. [14]
  Hexing SONG , Zan SUN . Synthesis, crystal structure, Hirshfeld surface analysis, and fluorescent sensing for Fe³⁺ of an Mn(Ⅱ) complex based on 1-naphthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 885-892. doi: 10.11862/CJIC.20240402
15. [15]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . Thickness-Insensitive, Cyano-Modified Perylene Diimide Derivative as a Cathode Interlayer Material for High-Efficiency Organic Solar Cells. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-0. doi: 10.3866/PKU.WHXB202406007
16. [16]
  Yangrui Xu , Yewei Ren , Xinlin Liu , Hongping Li , Ziyang Lu . NH₂-UIO-66 Based Hydrophobic Porous Liquid with High Mass Transfer and Affinity Surface for Enhancing CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(11): 2403032-0. doi: 10.3866/PKU.WHXB202403032
17. [17]
  Kun WANG , Wenrui LIU , Peng JIANG , Yuhang SONG , Lihua CHEN , Zhao DENG . Hierarchical hollow structured BiOBr-Pt catalysts for photocatalytic CO₂ reduction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1270-1278. doi: 10.11862/CJIC.20240037
18. [18]
  Fan Yang , Zheng Liu , Da Wang , KwunNam Hui , Yelong Zhang , Zhangquan Peng . Preparation and Properties of P-Bi₂Te₃/MXene Superstructure-based Anode for Potassium-Ion Battery. Acta Physico-Chimica Sinica, 2024, 40(2): 2303006-0. doi: 10.3866/PKU.WHXB202303006
19. [19]
  Tieping CAO , Yuejun LI , Dawei SUN . Surface plasmon resonance effect enhanced photocatalytic CO₂ reduction performance of S-scheme Bi₂S₃/TiO₂ heterojunction. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 903-912. doi: 10.11862/CJIC.20240366
20. [20]
  Peng ZHOU , Xiao CAI , Qingxiang MA , Xu LIU . Effects of Cu doping on the structure and optical properties of Au₁₁(dppf)₄Cl₂ nanocluster. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1254-1260. doi: 10.11862/CJIC.20240047

Get Citation

PDF

XML

Metrics

PDF Downloads(11)
Abstract views(774)
HTML views(105)

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