Issue 4, 2015

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
21 Sep 2014
Accepted
06 Feb 2015
First published
11 Feb 2015

Org. Chem. Front., 2015,2, 372-377

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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