Dodson E M, Lawson T E, Lai-Morrice J, Emerit H, Guest D P, Panther L A, Gonzalez-Mendez R, Roe S M, Goodall C A I, Bagley M C, Spencer J, Greenland B W
Department of Chemistry, Arundel Building 305, School of Life Sciences, University of Sussex, Falmer, BN1 9QJ, Brighton, UK.
113 Botanicals, 398 Montrose Avenue, SL1 4TJ, Slough, UK.
Chemistry. 2025 Feb 12;31(9):e202403217. doi: 10.1002/chem.202403217. Epub 2025 Jan 23.
The synthesis of 9 core-functionalised naphthalene diimide (c-NDI) residues is reported via a 3-step synthesis from naphthalenetetracarboxylic dianhydride using only mechanochemical activation. Selective dibromination and subsequent diimidization were achieved for the first time in a vibratory ball mill, resulting in the key structural intermediate, 2,6-dibromonaphthalenediimide (DBND), which is the basis for elaboration into a multitude of organic electronic materials. Our new synthesis of DBND is achieved in just 5 hours reaction time over two steps compared to typical solution state times of 24 hours. Subsequent Heck-type cross coupling reactions, with a range of styrene residues, produced a series of c-NDIs in good yields. The Heck-type reactions are rapid (1.5 hours), require no additional heating or solvent and are tolerant of atmospheric moisture and air.
报道了通过仅使用机械化学活化从萘四羧酸二酐经三步合成法合成9个核心功能化萘二亚胺（c-NDI）残基。首次在振动球磨机中实现了选择性二溴化和随后的二亚胺化，得到了关键结构中间体2,6-二溴萘二亚胺（DBND），它是制备多种有机电子材料的基础。与典型的溶液状态下24小时的反应时间相比，我们合成DBND的新方法只需两步，反应时间仅为5小时。随后，与一系列苯乙烯残基进行Heck型交叉偶联反应，以良好的产率得到了一系列c-NDI。Heck型反应速度快（1.5小时），无需额外加热或溶剂，并且耐受大气湿度和空气。
