Synthesis of monolateral and bilateral sulfur-heterocycle fused naphthalene diimides (NDIs) from monobromo and dibromo NDIs

Literature Information

Publication Date 2015-02-11
DOI 10.1039/C4QO00252K
Impact Factor 5.281
Authors

Bing Leng, Xueshun Jia, Xiaodi Yang, Xike Gao


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Abstract

Monolateral and bilateral sulfur-heterocycle fused naphthalene diimides (NDIs) are successfully synthesized from monobromo and dibromo NDIs via nucleophilic aromatic substitution reactions (SNAr) and the subsequent oxidative aromatization processes. The bromo-substituted monolateral fused NDI can be further functionalized with other aromatic or heteroaromatic rings to construct new electron-deficient π-functional materials with fine-tuned molecular orbital energy levels. The low-lying LUMO levels of these materials afford them great potential as n-type organic semiconductors.

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Organic Chemistry Frontiers

Organic Chemistry Frontiers
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Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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