{"title":"Structural and electronic tuning of single-benzene fluorophores with simple methylations","authors":"","doi":"10.1016/j.dyepig.2024.112523","DOIUrl":null,"url":null,"abstract":"<div><div>Recent advancements in the development of low molecular-weight fluorophores have led to the study of a single-benzene fluorophore (SBF) containing both electron-withdrawing and electron-donating groups within an aromatic ring, resulting in unique photophysical properties. In this study, we explored the modulation of emissions by adjusting the electron-donating properties via the simple methylation of the 2,5-diamino or 2,5-dihydroxy terephthalate structure. Introducing additional functional groups under both symmetrical and unsymmetrical conditions demonstrated changes in the photophysical properties, which was not only owing to the structural variations in the location and number of methyl groups but also due to alterations in the electron-donating properties. The observed effects appeared to be owing to the interactions between the amine and ester groups, as confirmed via single-crystal X-ray diffraction. Finally, hydrolysis of the ester to the corresponding carboxylic acid resulted in various emission wavelengths at different pH values via protonation and deprotonation. This study provides valuable insights for predicting the structural and electronic effects of additional functional groups in SBF.</div></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":null,"pages":null},"PeriodicalIF":4.1000,"publicationDate":"2024-10-29","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/S0143720824005898","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
Recent advancements in the development of low molecular-weight fluorophores have led to the study of a single-benzene fluorophore (SBF) containing both electron-withdrawing and electron-donating groups within an aromatic ring, resulting in unique photophysical properties. In this study, we explored the modulation of emissions by adjusting the electron-donating properties via the simple methylation of the 2,5-diamino or 2,5-dihydroxy terephthalate structure. Introducing additional functional groups under both symmetrical and unsymmetrical conditions demonstrated changes in the photophysical properties, which was not only owing to the structural variations in the location and number of methyl groups but also due to alterations in the electron-donating properties. The observed effects appeared to be owing to the interactions between the amine and ester groups, as confirmed via single-crystal X-ray diffraction. Finally, hydrolysis of the ester to the corresponding carboxylic acid resulted in various emission wavelengths at different pH values via protonation and deprotonation. This study provides valuable insights for predicting the structural and electronic effects of additional functional groups in SBF.
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.