Citation: Qian Yong, Yang Po, Wang Jianjun, Hu Junwei, Dong Chong. Synthesis and Properties of A Novel Bis-Schiff Base Derived from 2-Furaldehyde and N-ethyl-3, 6-diaminocarbazole[J]. Chemistry, ;2017, 80(12): 1138-1142. shu

Synthesis and Properties of A Novel Bis-Schiff Base Derived from 2-Furaldehyde and N-ethyl-3, 6-diaminocarbazole

Qian Yong ^1,2, ,
Yang Po ¹ ,
Wang Jianjun ¹ ,
Hu Junwei ¹ ,
Dong Chong ¹

1.
School of Chemistry, Biology and Material Engineering, Suzhou University of Science and Technology, Suzhou 215009
2.
Jiangsu Key Laboratory of Environmental Functional Material, Suzhou 215009

Received Date: 7 April 2017
Accepted Date: 28 August 2017

Figures(6)

With carbazole as raw material, the intermediate N-ethyl-3, 6-diaminocarbazole was synthesized through N-alkyl substitution, nitration and reduction reaction successively. Then a novel bis-Schiff base N-ethyl-3, 6-bis(2-furalideneimino)carbazole was synthesized from 2-furaldehyde and N-ethyl-3, 6-diaminocarbazole with a yield of 72.36%. Its structure was characterized by elemental analysis, FTIR, UV-Vis, ¹H NMR and EIS-MS. Solution fluorescence, solid fluorescence spectroscopy, cyclic voltammetry (CV) and TG-DTA thermal analysis were used to study its optical properties, electrochemical properties and thermal stability. The results showed that the target compound has a strong and wide UV absorption band from 200nm to 400nm in the dilute solution of DMF, and a deep blue fluorescence emission peak at 446nm excited by 365nm. Solid fluorescence spectroscopy indicated that the Schiff base has an emission peak at 467nm, with a 21nm red shift compared to the solution fluorescence. The optical band gap (E_g), ionization potential (I_p) and electron affinity (E_A) of the target compound are 2.19, 4.99 and 2.80 eV, respectively, calculated from UV-Vis and CV test, which indicated that it has excellent hole and electron transporting performance. TG-DTA analysis showed that the target compound possess good thermal stability. This compound has potential applications in organic luminescence, hole injection and transport materials and electron transport materials.
- N-ethyl-3,
- 6-diaminocarbazole,
- Bis-Schiff basse,
- Luminescent material
1. [1]
  C W Tang, S A VanSlyke, C H Chen. J. Appl. Phys., 1989, 65(9):3610~3616.
2. [2]
  L H Chan, R H Lee, C E Hsieh et al. J. Am. Chem. Soc., 2002, 124(22):6469~6479.
3. [3]
  G M Farinola, R Ragni. Chem. Soc. Rev., 2011, 40(7):3467~3482.
4. [4]
  W Qin, Z Yang, Y Jiang et al. Chem. Mater., 2015, 27(11):3892~3901.
5. [5]
6. [6]
7. [7]
8. [8]
  F Dumur. Org. Electron., 2015, 25:345~361.
9. [9]
  A Bucinskas, D Volyniuk, Y Danyliv et al. RSC Adv., 2015, 5(95):78150~78159.
10. [10]
  M Reig, C Gozalvez, R Bujaldon et al. Dyes Pigments, 2017, 137:24~35.
11. [11]
  H Husu, R Siikanen, J Makitalo et al. Nano Lett., 2012, 12(2):673~677.
12. [12]
  Z S Wang, N Koumura, Y Cui et al. Chem. Mater., 2008, 20(12):3993~4003.
13. [13]
  M Reig, G Bubniene. W Cambarau et al. RSC Adv., 2016, 6(11):9247~9253.
14. [14]
  P Kotchapradist, N Prachumrak, R Tarsang et al. J. Mater. Chem. C, 2013, 1(32):4916~4924.
15. [15]
16. [16]
17. [17]
  S Kotowicz, M Siwy, M Filapek et al. J. Lumin., 2017, 183:458~469.
18. [18]
19. [19]
  E Puodziukynaite, E Burbulis, J V Grazulevicius et al. Synth. Met., 2008, 158(21-24):993~998.
20. [20]
21. [21]
  J H Lee, J W Park, S K Choi. Synth. Met., 1997, 88(1):31~35.
22. [22]
23. [23]
24. [24]
  Q Kong, D Zhu, Y Quan et al. Chem. Mater., 2007, 19(13):3309~3318.
25. [25]
  C Adachi, T Tsutsui, S Saito. Appl. Phys. Lett., 1989, 55(15):1489~1491.
26. [26]
27. [27]
  L Y Bian, G Sun, Y X Sun et al. J. Phys. Org. Chem., 2012, 25(12):1112~1118.
1. [1]
  Fan JIA , Wenbao XU , Fangbin LIU , Haihua ZHANG , Hongbing FU . Synthesis and electroluminescence properties of Mn²⁺ doped quasi-two-dimensional perovskites (PEA)₂Pb_yMn_1-yBr₄. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1114-1122. doi: 10.11862/CJIC.20230473
2. [2]
  YanYuan Jia , Rong Rong , Jie Liu , Jing Guo , GuoYu Jiang , Shuo Guo . Unity is Strength, and Independence Shines: A Science Popularization Experiment on AIE and ACQ Effects. University Chemistry, 2024, 39(9): 349-358. doi: 10.12461/PKU.DXHX202402035
3. [3]
  Yanyang Li , Zongpei Zhang , Kai Li , Shuangquan Zang . Ideological and Political Design for the Comprehensive Experiment of the Synthesis and Aggregation-Induced Emission (AIE) Performance Study of Salicylaldehyde Schiff-Base. University Chemistry, 2024, 39(2): 105-109. doi: 10.3866/PKU.DXHX202307020
4. [4]
  Xiaofeng Xia , Jielian Zhu . Innovative Comprehensive Experimental Design: Synthesis of 6-Fluoro-N-benzoyl Tetrahydroquinoline. University Chemistry, 2024, 39(10): 344-352. doi: 10.12461/PKU.DXHX202405063
5. [5]
  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
6. [6]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
7. [7]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
8. [8]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
9. [9]
  Han ZHANG , Jianfeng SUN , Jinsheng LIANG . Hydrothermal synthesis and luminescent properties of broadband near-infrared Na₃CrF₆ phosphor. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 349-356. doi: 10.11862/CJIC.20240098
10. [10]
  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
11. [11]
  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
12. [12]
  Zhilian Liu , Wengui Wang , Hongxiao Yang , Yu Cui , Shoufeng Wang . Ideological and Political Education Design for the Synthesis of Irinotecan Drug Intermediate 7-Ethyl Camptothecin. University Chemistry, 2024, 39(2): 89-93. doi: 10.3866/PKU.DXHX202306012
13. [13]
  Baohua LÜ , Yuzhen LI . Anisotropic photoresponse of two-dimensional layered α-In₂Se₃(2H) ferroelectric materials. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1911-1918. doi: 10.11862/CJIC.20240105
14. [14]
  Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α_1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
15. [15]
  Guangming YIN , Huaiyao WANG , Jianhua ZHENG , Xinyue DONG , Jian LI , Yi'nan SUN , Yiming GAO , Bingbing WANG . Preparation and photocatalytic degradation performance of Ag/protonated g-C₃N₄ nanorod materials. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1491-1500. doi: 10.11862/CJIC.20240086
16. [16]
  Cheng Zheng , Shiying Zheng , Yanping Zhang , Shoutian Zheng , Qiaohua Wei . Synthesis, Copper Content Analysis, and Luminescent Performance Study of Binuclear Copper (I) Complexes with Isomeric Luminescence Shift: A Comprehensive Chemical Experiment Recommendation. University Chemistry, 2024, 39(7): 322-329. doi: 10.3866/PKU.DXHX202310131
17. [17]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393
18. [18]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
19. [19]
  Shijie Li , Ke Rong , Xiaoqin Wang , Chuqi Shen , Fang Yang , Qinghong Zhang . Design of Carbon Quantum Dots/CdS/Ta₃N₅ S-Scheme Heterojunction Nanofibers for Efficient Photocatalytic Antibiotic Removal. Acta Physico-Chimica Sinica, 2024, 40(12): 2403005-. doi: 10.3866/PKU.WHXB202403005
20. [20]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C₃N₄纳米片用于高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021

Get Citation

PDF

XML

Metrics

PDF Downloads(12)
Abstract views(2205)
HTML views(845)

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