AI Article Synopsis
- Researchers developed a new method to synthesize 9 core-functionalised naphthalene diimide (c-NDI) compounds using a three-step, solvent-free process that activates chemicals mechanically.
- They achieved selective dibromination of naphthalenetetracarboxylic dianhydride in a vibratory ball mill, producing a key intermediate (2,6-dibromonaphthalenediimide) quickly and efficiently within 5 hours, significantly faster than traditional methods.
- The study also successfully executed rapid Heck-type cross coupling reactions with various styrene residues, resulting in good yields of c-NDIs without the need for extra heating or solvents, making the process robust against environmental conditions.
Article Abstract
The synthesis of 9 core-functionalised naphthalene diimide (c-NDI) residues is reported via a 3-step solvent free synthesis from naphthalenetetracarboxylic dianhydride using only mechanochemical activation. Selective dibromination and subsequent dimidiation 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.
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| http://dx.doi.org/10.1002/chem.202403217 | DOI Listing |
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