Bis((9H-(4,5-diazafluoren)-9-ylidene)methyl)arylenes: Design, synthesis, optoelectronic properties, sensorics and luminescent coordination polymers

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED Dyes and Pigments Pub Date : 2024-06-06 DOI:10.1016/j.dyepig.2024.112261

Darya S. Cheshkina, Christina S. Becker, Alina A. Sonina, Igor P. Koskin, Inna K. Shundrina, Maxim S. Kazantsev

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Abstract

Aggregation-induced emission (AIE) materials are highly demanded for practical applications in optoelectronics, sensorics, material science and bio-imaging. However, highly torsionally-flexible and hybrid organic/inorganic AIE materials are limited. In this work we designed, synthesized and comprehensively studied AIE-active bis((9H-(4,5-diazafluoren)-9-ylidene)methyl)arylenes demonstrating high torsional freedom coupled with electron-accepting character and N,N′-chelating ability. One-rotor nonplanar structure of phenylene-linked derivative (BDFMP) allowed us to demonstrate its polymorphic diversity both in neat state and in coordination polymers. X-ray diffraction analysis indicated formation of crystals with extensive π-stacking interactions and slipped/side-by-side packing motifs, the former crystals demonstrating a photoluminescence quantum yield of 25 %. The reaction of both BDFMP/BDFMT with ZnCl₂ resulted in formation of unique coordination polymers and porous metal organic frameworks with photoluminescence sensitive to heating and (de/re)hydratation. The latter effect was exploited for security painting and anti-counterfeiting demonstration.

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双((9H-(4,5-二氮芴)-9-亚基)甲基)芳基：设计、合成、光电特性、传感和发光配位聚合物

聚合诱导发射（AIE）材料在光电子学、传感器、材料科学和生物成像等领域的实际应用中需求量很大。然而，具有高度扭转柔性的有机/无机混合 AIE 材料却十分有限。在这项工作中，我们设计、合成并全面研究了具有 AIE 活性的双((9H-(4,5-二氮杂芴)-9-亚基)甲基)芳基，它们具有高扭转自由度、电子接受特性和 N,N′-螯合能力。苯连系衍生物 (BDFMP) 的单转子非平面结构使我们得以展示其在纯态和配位聚合物中的多态性。X 射线衍射分析表明，形成的晶体具有广泛的 π 堆积相互作用和滑动/并排堆积图案，前者的光量子产率为 25%。BDFMP/BDFMT 与 ZnCl2 反应可形成独特的配位聚合物和多孔金属有机框架，其光致发光对加热和（脱/再）水合反应敏感。后一种效应被用于安全喷漆和防伪演示。

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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.