Miao Yang , Jingwen Guo , Shijie Fu , Yuhan Zhang , Longmei Yang , Qian Li , Yan Bao , Chengyuan Wang
{"title":"Packing structures and piezochromic properties engineering through F functionalization in 4-position substituted coumarin based organic luminogens","authors":"Miao Yang , Jingwen Guo , Shijie Fu , Yuhan Zhang , Longmei Yang , Qian Li , Yan Bao , Chengyuan Wang","doi":"10.1016/j.dyepig.2025.113055","DOIUrl":null,"url":null,"abstract":"<div><div>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, <em>etc</em>. In this work, four coumarin derivatives (<strong>4-CPF1</strong>, <strong>4-CPF2</strong>, <strong>4-CPF3</strong>, and <strong>4-CPFM</strong>) 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 <strong>4-CPF2</strong>, and in particular, <strong>4-CPF3</strong> and <strong>4-CPFM</strong> 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.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":"243 ","pages":"Article 113055"},"PeriodicalIF":4.2000,"publicationDate":"2025-07-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Dyes and Pigments","FirstCategoryId":"88","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0143720825004255","RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
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.
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.