Packing structures and piezochromic properties engineering through F functionalization in 4-position substituted coumarin based organic luminogens

IF 4.2 3区 工程技术 Q2 CHEMISTRY, APPLIED
Miao Yang , Jingwen Guo , Shijie Fu , Yuhan Zhang , Longmei Yang , Qian Li , Yan Bao , Chengyuan Wang
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引用次数: 0

Abstract

Organic luminogens (OLs) exhibiting piezochromic (PC) properties upon external force stimuli have attracted much research interests due to their great application potentials as pressure sensors, anti-counterfeiting materials, etc. In this work, four coumarin derivatives (4-CPF1, 4-CPF2, 4-CPF3, and 4-CPFM) with fluorine modified phenyl substituents at 4-position were designed and synthesized, in which the number and positions of the F atoms are differed. Their single-crystal structures were successfully determined to elucidate the molecular conformations and packing structures, and their photophysical properties in both diluted solution and the aggregated state were studied by various spectroscopic analysis. The PC properties of these materials were investigated by both mechanical grinding (MG) and applying hydrostatic pressure (HP). Upon MG, these materials all show PC responses except for 4-CPF2, and in particular, 4-CPF3 and 4-CPFM exhibit certain self-recovery under ambient conditions. Under HP, all these materials reveal typical PC properties with different pressure coefficients of emission wavelength, and the reversibility of their fluorescence is varied as well, depending on the position and number of F substitutions. The differences in the PC properties, both upon MG and under HP, are well correlated with their molecular organizations and packing structures in the aggregated state. Our study not only confirms the great application potentials of coumarin derivatives with 4-position substituents as PC materials, but also indicates that F functionalization is an effective strategy for tuning the aggregated-state structures of coumarin based OLs, together with their photophysical and PC properties.
4位取代香豆素基有机发光素的F功能化填料结构和压致变色性能工程
在外力刺激下表现出压致变色特性的有机发光材料在压力传感器、防伪材料等方面具有很大的应用潜力,引起了人们的广泛关注。本文设计并合成了4-CPF1、4-CPF2、4-CPF3和4-CPFM 4种4位苯基取代氟基香豆素衍生物,其中F原子的数目和位置不同。成功地确定了它们的单晶结构,以阐明分子构象和堆积结构,并通过各种光谱分析研究了它们在稀释溶液和聚集状态下的光物理性质。采用机械研磨(MG)和静水压力(HP)两种方法研究了这些材料的PC性能。MG作用下,除4-CPF2外,其余材料均表现出PC响应,特别是4-CPF3和4-CPFM在环境条件下表现出一定的自恢复。在高压下,这些材料在不同的发射波长压力系数下都表现出典型的PC性质,其荧光的可逆性也随F取代的位置和数量而变化。在MG和HP条件下,PC性能的差异与其聚集状态下的分子组织和填充结构密切相关。我们的研究不仅证实了4位取代基香豆素衍生物作为聚羧酸材料的巨大应用潜力,而且表明F官能化是调整香豆素基OLs的聚集态结构及其光物理和聚羧酸性质的有效策略。
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来源期刊
Dyes and Pigments
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.
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