Dual responsive behaviors in fluorescence of molecular crystals based on naphthalene pyridyl derivatives

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED Dyes and Pigments Pub Date : 2024-07-01 DOI:10.1016/j.dyepig.2024.112313

Tian-Le Zhang, Zhi-Bo Fan, Chen-Chen Zhang, Hui-Yao Lin, Da-Hui Qu, Fei Tong

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Abstract

Three compounds based on naphthalene and pyridine structures with different nitrogen positions (NP-2, NP-3, and NP-4) were synthesized. Except for displaying aggregation-induced emission (AIE) properties, the solution and crystals of these compounds show reversible fluorescence changes under alternative acid and base treatments. Experimental results, including X-ray diffraction, optical spectroscopy measurements, and cross-polarized microscope characterization, suggested that compounds might undergo reversible crystal-to-crystal transition upon external acid and base stimuli. It also revealed that the position of the heteroatom nitrogen in the pyridine unit significantly affected the intra- and intermolecular interactions, leading to restricted-intermolecular motions (RIMs) that caused the AIE effect. Besides, computational calculations indicated significant changes in molecular geometries and electronic interactions between the initial states and the protonated states. An information encryption system involving activation and operation codes was established based on the multiple stimuli-responsive properties. Our work not only presents a facile way to develop multiple responsive properties in molecular crystal systems but also explores their potential as highly emissive functional dyes for future applications.

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基于萘吡啶衍生物的分子晶体在荧光中的双重响应行为

我们合成了三种基于萘和吡啶结构且氮位不同的化合物（NP-2、NP-3 和 NP-4）。除了显示出聚集诱导发射（AIE）特性外，这些化合物的溶液和晶体在酸碱交替处理下显示出可逆的荧光变化。包括 X 射线衍射、光学光谱测量和交叉偏振显微镜表征在内的实验结果表明，这些化合物在外部酸碱刺激下可能会发生可逆的晶体-晶体转变。研究还发现，吡啶单元中杂原子氮的位置极大地影响了分子内和分子间的相互作用，导致分子间运动受限（RIMs），从而引发了 AIE 效应。此外，计算表明，初始态与质子化态之间的分子几何结构和电子相互作用发生了显著变化。基于多重刺激响应特性，我们建立了一个包含激活码和操作码的信息加密系统。我们的工作不仅提供了一种在分子晶体系统中开发多重响应特性的简便方法，而且探索了它们作为高发射功能染料在未来应用中的潜力。

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来源期刊

Dyes and Pigments 工程技术-材料科学：纺织

CiteScore

8.20

自引率

13.30%

发文量

933

审稿时长

33 days

期刊介绍： Dyes and Pigments covers the scientific and technical aspects of the chemistry and physics of dyes, pigments and their intermediates. Emphasis is placed on the properties of the colouring matters themselves rather than on their applications or the system in which they may be applied. Thus the journal accepts research and review papers on the synthesis of dyes, pigments and intermediates, their physical or chemical properties, e.g. spectroscopic, surface, solution or solid state characteristics, the physical aspects of their preparation, e.g. precipitation, nucleation and growth, crystal formation, liquid crystalline characteristics, their photochemical, ecological or biological properties and the relationship between colour and chemical constitution. However, papers are considered which deal with the more fundamental aspects of colourant application and of the interactions of colourants with substrates or media. The journal will interest a wide variety of workers in a range of disciplines whose work involves dyes, pigments and their intermediates, and provides a platform for investigators with common interests but diverse fields of activity such as cosmetics, reprographics, dye and pigment synthesis, medical research, polymers, etc.