Synthesis of Pyridin-1(2<i>H</i>)-ylacrylates and the Effects of Different Functional Groups on Their Fluorescence
Weiguang Yang,
Danyang Luo,
Guanrong Li,
Qiaoli Luo,
Martin G. Banwell,
Lanmei Chen
Affiliations
Weiguang Yang
Key Laboratory of Big Data Mining and Precision Drug Design of Guangdong Medical University, The Marine Biomedical Research Institute, Guangdong Medical University, Zhanjiang 524023, China
Danyang Luo
Key Laboratory of Big Data Mining and Precision Drug Design of Guangdong Medical University, The Marine Biomedical Research Institute, Guangdong Medical University, Zhanjiang 524023, China
Guanrong Li
Key Laboratory of Big Data Mining and Precision Drug Design of Guangdong Medical University, The Marine Biomedical Research Institute, Guangdong Medical University, Zhanjiang 524023, China
Qiaoli Luo
School of Chemistry and Chemical Engineering, Lingnan Normal University, Zhanjiang 524048, China
Martin G. Banwell
Key Laboratory of Big Data Mining and Precision Drug Design of Guangdong Medical University, The Marine Biomedical Research Institute, Guangdong Medical University, Zhanjiang 524023, China
Lanmei Chen
Key Laboratory of Big Data Mining and Precision Drug Design of Guangdong Medical University, The Marine Biomedical Research Institute, Guangdong Medical University, Zhanjiang 524023, China
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.
