ArticleChemistry (Weinheim an der Bergstrasse, Germany)2025
Synthesis of Core-Functionalised Naphthalenediimides from Naphthalenetetracarboxylic Dianhydride using a Vibratory Ball Mill: Bromination, Imidization and Heck-Type Reactions.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed.
- A Mechanical Planar Chiral Rotaxane Induces Single-Handed Helicity in a Twisted Perylene Diimide.Angewandte Chemie (International ed. in English) · 2026Article
- Synthesis of Core-Functionalised Naphthalenediimides from Naphthalenetetracarboxylic Dianhydride using a Vibratory Ball Mill: Bromination, Imidization and Heck-Type Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
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12 authors.
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Abstract
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.
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