Synthesis and Properties of 1,1-bis (benzo imidazole-2-yl)- 2-(N-ethyl carbazole-3-yl) Ethylene

QIAN Yong; WANG Jian-jun; ZHANG Rong; XU Yan-mei

doi:10.3788/fgxb20143506.0660

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Synthesis and Properties of 1,1-bis (benzo imidazole-2-yl)- 2-(N-ethyl carbazole-3-yl) Ethylene

更新时间：2020-08-12

- Synthesis and Properties of 1,1-bis (benzo imidazole-2-yl)- 2-(N-ethyl carbazole-3-yl) Ethylene
- Chinese Journal of Luminescence Vol. 35, Issue 6, Pages: 660-665(2014)
- 作者机构：
  
  1. 苏州科技大学化学生物与材料工程学院,江苏苏州,215009
  2. 江苏省环境功能材料重点实验室,江苏苏州,215009
- 作者简介：
- 基金信息：
- DOI：10.3788/fgxb20143506.0660
  CLC： O626.23;TQ252.3
- Received：13 January 2014，
  
  Revised：14 April 2014，
  
  Published：03 June 2014
- 稿件说明：
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钱永, 王建军, 张蓉等. 1，1-二（苯并咪唑-2-基）-2-（N-乙基咔唑-3-基）乙烯的合成及其性能研究[J]. 发光学报, 2014,35(6): 660-665

QIAN Yong, WANG Jian-jun, ZHANG Rong etc. Synthesis and Properties of 1,1-bis (benzo imidazole-2-yl)- 2-(N-ethyl carbazole-3-yl) Ethylene[J]. Chinese Journal of Luminescence, 2014,35(6): 660-665
钱永, 王建军, 张蓉等. 1，1-二（苯并咪唑-2-基）-2-（N-乙基咔唑-3-基）乙烯的合成及其性能研究[J]. 发光学报, 2014,35(6): 660-665 DOI： 10.3788/fgxb20143506.0660.

QIAN Yong, WANG Jian-jun, ZHANG Rong etc. Synthesis and Properties of 1,1-bis (benzo imidazole-2-yl)- 2-(N-ethyl carbazole-3-yl) Ethylene[J]. Chinese Journal of Luminescence, 2014,35(6): 660-665 DOI： 10.3788/fgxb20143506.0660.

摘要

以六氢吡啶为催化剂，通过Vilsmerier-Haack和Knoevenagel反应合成了一种新型的芳稠杂环化合物1，1-二（苯并咪唑-2-基）-2-（N-乙基咔唑-3-基）乙烯，产率为72.53%。利用元素分析、FT-IR、UV-Vis、

H NMR、溶液和固体荧光光谱、循环伏安（CV）分析、TG-DTA热分析研究了产物的结构、光学特性、电化学特性和热稳定性。该化合物在DMF、DMSO和DCM 3种溶剂的稀溶液中均具有290 nm和375 nm两处紫外吸收峰以及470 nm处的蓝绿色荧光发射。不同DMSO和DCM体积比的混合溶剂的溶液荧光表明，该化合物具有明显的AIE荧光效应。固体荧光光谱表明，产物在327 nm和436 nm有两处激发峰，最大发射峰位于484 nm，相比于溶液荧光发生了红移现象。由循环伏安测试结果计算获得产物的能隙为2.79 eV，电离势为5.43 eV，电子亲和势为2.85 eV，表明产物具有良好的电子传输能力。TG/DTA测试结果显示目标产物具有良好的热稳定性。

Abstract

A novel aromatic fused heterocyclic 1

1-bis(2-benzoimididazole-yl)-2-(N-ethyl carbazole-3-yl)ethylene was synthesized by Vilsmerier-Haack reaction and Knoevenagel reaction using piperdine as catalyst with a yield of 72.53%. Elemental analysis

FT-IR

UV-Vis

H NMR

solution fluorescence

solid fluorescence spectroscopy

cyclic voltammetry electrochemical analysis and TG-DTA thermal analysis were used to study its structure

optical properties

electrochemical properties and thermal stability. The results show that this compound has two UV absorption peaks at 290 nm and 375 nm in the dilute solution of DMF

DMSO and DCM

and a blue-green fluorescence emission peak at 470 nm excited by 375 nm. A significant AIE effect was found through solution fluorescence tests with different

(DMSO):

(DCM) mixed solvent of this compound. Solid fluorescence spectroscopy indicate that the product has two excitation peaks at 327 and 436 nm and an emission peak at 484nm with red shift compared to the solution fluorescence. Cyclic voltammetry (CV) was employed to characterize the

HOMO

and

of this compound

which are 2.58

5.43

2.85 eV

respectively. This result shows that it has good hole transporting ability and good electron transporting capability. TG/DTA analysis shows that the target product possesses good thermal stability.

关键词

Keywords

references

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