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Keywords = pyridin-1(2H)-ylacrylates

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15 pages, 3443 KiB  
Article
Synthesis of Pyridin-1(2H)-ylacrylates and the Effects of Different Functional Groups on Their Fluorescence
by Weiguang Yang, Danyang Luo, Guanrong Li, Qiaoli Luo, Martin G. Banwell and Lanmei Chen
Molecules 2023, 28(18), 6511; https://doi.org/10.3390/molecules28186511 - 8 Sep 2023
Cited by 1 | Viewed by 1574
Abstract
While fluorescent organic materials have many potential as well as proven applications and so have attracted significant attention, pyridine–olefin conjugates remain a less studied subset of such systems. Herein, therefore, we report on the development of the straightforward syntheses of pyridin-1(2H)-ylacrylates [...] Read more.
While fluorescent organic materials have many potential as well as proven applications and so have attracted significant attention, pyridine–olefin conjugates remain a less studied subset of such systems. Herein, therefore, we report on the development of the straightforward syntheses of pyridin-1(2H)-ylacrylates and the outcomes of a study of the effects of substituents on their fluorescent properties. Such compounds were prepared using a simple, metal-free and three-component coupling reaction involving 2-aminopyridines, sulfonyl azides and propiolates. The fluorescent properties of the ensuing products are significantly affected by the positions of substituents on the cyclic framework, with those located in central positions having the greatest impact. Electron-withdrawing groups tend to induce blue shifts while electron-donating ones cause red shifts. This work highlights the capacity that the micro-modification of fluorescent materials provides for fine-tuning their properties such that they may be usefully applied to, for example, the study of luminescent materials. Full article
(This article belongs to the Special Issue Novelties in N-Heterocycles Chemistry: From Synthesis to Application)
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