Department of Chemistry and Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University , Evanston, Illinois 60208-3113, United States.
Org Lett. 2014 Feb 7;16(3):696-9. doi: 10.1021/ol403736m. Epub 2014 Jan 13.
A series of electron-deficient perylene and naphthalene imides and diimides (1-4) with varying degrees of trifluoromethylation were synthesized. Single crystal X-ray analysis afforded detailed structural information, while spectroelectrochemical and EPR spectroscopy provided characterization of the radical anions of 1-4. This study reveals that trifluoromethylation of the imides and diimides makes their one-electron reduction potentials substantially more positive relative to the unsubstituted counterparts, while their other properties remain largely unchanged.
合成了一系列具有不同程度三氟甲基化的缺电子苝和萘酰亚胺及二酰亚胺（1-4）。单晶 X 射线分析提供了详细的结构信息，而光谱电化学和 EPR 光谱则对 1-4 的自由基阴离子进行了表征。这项研究表明，酰亚胺和二酰亚胺的三氟甲基化使得它们的单电子还原电位相对于未取代的对应物显著更正，而它们的其他性质基本保持不变。
