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Issue 4, 2015
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Synthesis of monolateral and bilateral sulfur-heterocycle fused naphthalene diimides (NDIs) from monobromo and dibromo NDIs

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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.

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

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The article was received on 21 Sep 2014, accepted on 06 Feb 2015 and first published on 11 Feb 2015


Article type: Research Article
DOI: 10.1039/C4QO00252K
Citation: Org. Chem. Front., 2015,2, 372-377

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

    B. Leng, D. Lu, X. Jia, X. Yang and X. Gao, Org. Chem. Front., 2015, 2, 372
    DOI: 10.1039/C4QO00252K

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