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
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