Tetraphenylethylene or Naphthalimide-Functionalized Dendritic Carbazole AIEgens: Self-Assembly Visualization, Three Disparate Force-Triggered Fluorescence Responses, and Advanced Anticounterfeiting Applications

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-04-29 DOI:10.1039/d5qo00393h

Yijie Zou, Zhao Chen, Fei Zhao, Ya Yin, Kaixin He, Xingru Liang, Haifeng He, Zhijian Li, Shenghua Liu

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引用次数: 0

Abstract

Three 1,8-naphthalimide-modified donor-π-acceptor type and three tetraphenylethylene-functionalized fluorogenic dendritic carbazole derivatives are designed and synthesized. These six dendrimer-like carbazole-containing compounds are typical aggregation-induced emission (AIE) luminogens. Specially, the AIE-active 3CzB2Nap possessing trimeric carbazole and two 1,8-naphthalimide groups is featured by aggregation-triggered self-assembly, and the visualization of its intriguing self-assembly process is successfully realized through scanning electron microscopy technology. Notably, three types of contrasting anisotropic mechanical force-induced fluorescence responses from the six prepared dendritic carbazole AIEgens are observed. More specifically, 7CzB2TPE and 3CzB2Nap do not exhibit fluorescence changes after grinding; 1CzB2TPE and 3CzB2TPE display irreversible mechanofluorochromic phenomena; 1CzB2Nap and 7CzB2Nap show reversible mechanofluorochromic characteristics. To deeply elucidate their three distinct types of force-responsive emissive features of six dendritic AIEgens, powder and single-crystal X-ray diffraction, differential scanning calorimetry experiments, and theoretical simulation calculations of molecular packing structures before and after grinding are carried out. Based on the observed three disparate force-dependent fluorescence phenomena, two advanced information security systems involving multilevel painting anticounterfeit and multimode information encryption are elaborately constructed.

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四苯基乙烯或萘酰亚胺功能化的树突状咔唑原：自组装可视化，三种不同的力触发荧光响应，以及先进的防伪应用

设计合成了3个1,8-萘酰亚胺修饰的供体-π-受体型和3个四苯基乙烯功能化的荧光树突状咔唑衍生物。这六种树状咔唑类化合物是典型的聚集诱导发射（AIE）发光物质。特别地，含有三聚咔唑和两个1,8-萘酰亚胺基团的aie活性3CzB2Nap具有聚集触发自组装的特点，并通过扫描电镜技术成功地实现了其有趣的自组装过程的可视化。值得注意的是，从六种制备的树突状咔唑aigens中观察到三种不同类型的各向异性机械力诱导荧光响应。更具体地说，7CzB2TPE和3CzB2Nap在研磨后没有荧光变化；1CzB2TPE和3CzB2TPE显示不可逆的机械荧光现象；1CzB2Nap和7CzB2Nap表现出可逆的机械荧光特性。为了深入阐明六种枝晶AIEgens、粉末和单晶的三种不同类型的力响应发射特征，进行了差示扫描量热实验和研磨前后分子堆积结构的理论模拟计算。基于观察到的三种不同的力依赖荧光现象，精心构建了两种先进的信息安全系统，包括多层防伪和多模式信息加密。

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.