Enolate Enables Unexpected Red Luminescence from Through-Bond/Through-Space Complexation between Imide and Organic Base,Macromolecules

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Enolate Enables Unexpected Red Luminescence from Through-Bond/Through-Space Complexation between Imide and Organic Base
Macromolecules ( IF 5.1 ) Pub Date : 2023-12-05 , DOI: 10.1021/acs.macromol.3c01977
Yuan Xie _{1,

2,

3,

4} , Weihao Tu _{3,

4,

5} , Zuping Xiong _{3,

4,

5} , Dan Liu ₆ , Jianyu Zhang ₇ , Jing Zhi Sun _{3,

5} , Zheng Zhao ₆ , Dong Wang ₁ , Feihe Huang _{4,

8} , Haoke Zhang _{3,

4,

5} , Ben Zhong Tang ₆

Affiliation

Center for AIE Research, Shenzhen Key Laboratory of Polymer Science and Technology, Guangdong Research Center for Interfacial Engineering of Functional Materials, College of Materials Science and Engineering, Shenzhen University, Shenzhen 518061, China
College of Physics and Optoelectronic Engineering, Shenzhen University, Shenzhen 518060, China
MOE Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310058, China
Zhejiang-Israel Joint Laboratory of Self-Assembling Functional Materials, ZJU-Hangzhou Global Scientific and Technological Innovation Center, Zhejiang University, Hangzhou 311215, China
Centre of Healthcare Materials, Shaoxing Institute, Zhejiang University, Shaoxing 312000, China
School of Science and Engineering, Shenzhen Institute of Aggregate Science and Technology, The Chinese University of Hong Kong, Shenzhen (CUHK-Shenzhen), Guangdong518172, China
Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, and Guangdong-Hong Kong-Macau Joint Laboratory of Optoelectronic and Magnetic Functional Materials, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong 999077, China
Stoddart Institute of Molecular Science, Department of Chemistry, Zhejiang University, Hangzhou 310058, China

Maleimides have been commonly employed for color reactions in the last few decades, as they produce a bright color when treated with organic or inorganic base. For color formation or the luminescence mechanism, their chromophores have remained unexplored. In this study, we disclosed this well-known phenomenon with commercially available maleimide derivatives based on complex formation between maleimide/succinimide and the organic base of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). We provided direct experimental evidence of the polymerization process when maleimide is mixed with DBU. The maleimide/DBU complex emits prominent yellow-red fluorescence at long wavelengths due to its through-bond enolate complex formation between the maleimide-based polymer and DBU. DBU can also form an enolate complex with succinimide via a through-space manner, resulting in fluorescence emission similar to that of maleimide does. Their structures were rationally characterized and explored. Additionally, external factors including solvents and the aromatic ring effect can be applied to further stabilize the complex formation, which provides insights for designing novel fluorescent materials.

中文翻译：

烯醇化物能够通过酰亚胺和有机碱之间的键合/空间络合产生意想不到的红色发光

在过去的几十年里，马来酰亚胺通常用于颜色反应，因为它们在用有机或无机碱处理时会产生明亮的颜色。对于颜色形成或发光机制，它们的发色团仍未被探索。在这项研究中，我们利用市售的马来酰亚胺衍生物揭示了这一众所周知的现象，该衍生物基于马来酰亚胺/琥珀酰亚胺与 1,8-二氮杂双环[5.4.0]undec-7-ene (DBU) 有机碱之间的复合物形成。我们提供了马来酰亚胺与 DBU 混合时聚合过程的直接实验证据。由于马来酰亚胺基聚合物和 DBU 之间形成了直通键烯醇化物络合物，马来酰亚胺/DBU 络合物在长波长下发出显着的黄红色荧光。DBU还可以通过空间方式与琥珀酰亚胺形成烯醇络合物，从而产生类似于马来酰亚胺的荧光发射。它们的结构得到了合理的表征和探索。此外，可以应用包括溶剂和芳环效应在内的外部因素来进一步稳定复合物的形成，这为设计新型荧光材料提供了见解。

更新日期：2023-12-05

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