Preparation and Photoluminescent Properties of Polyimides Containing Triphenylamine Pendant Group

Lun-jun Qu; Li-shuang Tang; Si-wei Liu; Zhen-guo Chi; Xu-dong Chen; Yi Zhang; Jia-rui Xu

doi:10.11777/j.issn1000-3304.2018.18075

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Preparation and Photoluminescent Properties of Polyimides Containing Triphenylamine Pendant Group

Research Article | 更新时间：2021-01-26

- Preparation and Photoluminescent Properties of Polyimides Containing Triphenylamine Pendant Group
- Acta Polymerica Sinica Vol. 0, Issue 11, Pages: 1430-1441(2018)
- 作者机构：
  
  中山大学聚合物复合材料及功能材料教育部重点实验室高性能树脂基复合材料广东省重点实验室广东省高性能有机聚合物光电功能薄膜工程技术研究中心　广州 510275
- 作者简介：
- 基金信息：
- DOI：10.11777/j.issn1000-3304.2018.18075
  CLC：
- Published：2018-11，
  
  Received：7 March 2018，
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Lun-jun Qu, Li-shuang Tang, Si-wei Liu, Zhen-guo Chi, Xu-dong Chen, Yi Zhang, Jia-rui Xu. Preparation and Photoluminescent Properties of Polyimides Containing Triphenylamine Pendant Group. [J]. Acta Polymerica Sinica 0(11):1430-1441(2018)
DOI：

Lun-jun Qu, Li-shuang Tang, Si-wei Liu, Zhen-guo Chi, Xu-dong Chen, Yi Zhang, Jia-rui Xu. Preparation and Photoluminescent Properties of Polyimides Containing Triphenylamine Pendant Group. [J]. Acta Polymerica Sinica 0(11):1430-1441(2018) DOI： 10.11777/j.issn1000-3304.2018.18075.

摘要

通过分子结构设计，合成了2种结构相似、电子效应明显不同的含三苯胺结构二胺单体TPNDA和TPCDA. 所制备的2种二胺单体分别与2种芳香型二酐(BPADA、HQDPA)进行聚合反应，并通过热酰亚胺化法制备得到4种新型聚酰亚胺薄膜. 研究结果显示，4种聚酰亚胺薄膜均表现出优异的热稳定性，在紫外光照射下，含TPNDA结构的聚酰亚胺(TPNBPI、TPNHPI)没有呈现荧光特性，而含TPCDA结构的聚酰亚胺(TPCBPI

TPCHPI)均可发明显的橙色荧光. 对模型化合物的理论计算结果表明，共轭的TPNDA体系及不共轭的TPCDA体系均应为跃迁禁阻的不发光体系. 进一步的研究表明，含TPCDA结构的聚酰亚胺体系的发光性质主要源于以下两方面原因：(1)与N原子相比，sp

的碳原子隔断了三苯胺结构与聚合物主链酰亚胺环的共轭性，有利于消除聚酰亚胺分子内电荷转移效应对三苯胺(TPA)侧基的影响；(2)相对独立的侧基TPA可与聚酰亚胺分子主链之间发生强的分子间相互作用，该相互作用可导致该体系发射较强的橙色荧光. 其最大发射发光波长红移达184 nm，且发光强度明显增强.

Abstract

Two triphenylamines (TPA) based diamine monomers

TPCDA and TPNDA

were successfully designed and synthesized

which were of similar chemical structures but different electronic effects. Both TPCDA and TPNDA exhibit aggregation induced emission (AIE) phenomenon

and show intense emission at 395 and 447 nm in the solid state

respectively. They were polymerized with two dianhydrides (BPADA and HQDPA)

respectively

to form four novel polyimides with excellent thermal stability. The fluorescence of the polyimides derived from TPNDA

TPNBPI and TPNHPI

is totally quenched. However

for the TPCDA-based polyimides

TPCBPI and TPCHPI show bright orange photoluminescence at 565 and 585 nm in their films

respectively. By increasing the concentration of TPCBPI and TPNBPI in N-methyl pyrrolidone (NMP) solution

their emission changes from non-luminescence to bright blue emission

followed by a red-shift due to the formation of strong intermolecular charge transfer

and they show green emission at 504 nm and 508 nm at the concentration of 4 mg·mL

−1

. The photoluminescence of TPCDA-based polyimides is similar to the composite system

where TPA is doped in a polyimide with the same main-chain structure. However

the theoretical calculations for the model units of the resulting polyimides show that both the conjugated TPNDA-based system and the unconjugated TPCDA-based system are non-luminescent due to an inhibited transition from HOMO to LUMO level. Further studies show that the luminescent properties of the TPCDA-based polyimides are owing to the following two reasons: (1) Compared with the TPNDA-based system

the sp

hybridized carbon atom in the TPCDA-based system separates the TPA structure from the polyimide main chain

which dispels the influence of the intramolecular charge transfer effect of the polyimide on TPA; (2) The relatively independent TPA moieties can have strong intermolecular charge transfer interaction with the polyimide main chains

which leads this system to exhibiting a strong orange fluorescence with a 184 nm red-shift of the max emission wavelength. This work demonstrates a simple strategy to develop aromatic polyimides with high fluorescence for potential applications in organic photoelectric field.

关键词

聚酰亚胺三苯胺光致发光分子内电荷转移分子间电荷转移

Keywords

PolyimideTriphenylaminePhotoluminescenceIntramolecular CTCIntermolecular CTC

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Laboratory of Polymeric Composite and Functional Materials, Guangdong Laboratory of High-Performance Polymer Composites, Guangdong Engineering Technology Research Center for High-performance Organic and Polymer Photoelectric Functional Films, State Key Laboratory of Optoelectronic Materials and Technologies, School of Chemistry and Chemical Engineering, Sun Yat-sen University

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