New Di-, Tri-, and Tetra-Core-Functionalized Naphthalene Diimides from Reactions of Allyl Ethers with Lewis Acids

Core-substituted NDIs bearing aryl allyl ethers have a predisposition to deallylation in the presence of Lewis Acids (LA). However, under certain conditions, with appropriate choice of LA, the reaction can be controlled to yield unexpected and highly functionalized dinaphthol systems through a [3,3]-sigmatropic (Claisen) rearrangement. The major products of the rearrangement study have been characterized by X-ray crystallographic analysis and the per-substituted products are shown to undergo ring-closing metathesis to form heterocyclic core-extended NDIs. This study highlights a simple method to construct a series of important donor–acceptor building blocks for the preparation of new conjugated materials

New Di-, Tri-, and Tetra-Core-Functionalized Naphthalene Diimides from Reactions of Allyl Ethers with Lewis Acids

Core-substituted NDIs bearing aryl allyl ethers have a predisposition to deallylation in the presence of Lewis Acids (LA). However, under certain conditions, with appropriate choice of LA, the reaction can be controlled to yield unexpected and highly functionalized dinaphthol systems through a [3,3]-sigmatropic (Claisen) rearrangement. The major products of the rearrangement study have been characterized by X-ray crystallographic analysis and the per-substituted products are shown to undergo ring-closing metathesis to form heterocyclic core-extended NDIs. This study highlights a simple method to construct a series of important donor-acceptor building blocks for the preparation of new conjugated materials

Water-soluble Cu²⁺-fluorescent sensor based on core-substituted naphthalene diimide and its application in drinking water analysis and live cell imaging

Water-soluble naphthalene diimide based fluorescent chemosensor, N1, was designed for Cu2+ recognition. The sensor exhibited significant fluorescence modulation and chromogenic change with high Cu2+ sensitivity and selectivity over interfering metal ions. The sensor was able to efficiently monitor Cu2+ in 100% aqueous buffer solution with a low detection limit of 0.7 ppb which is much lower than the recommended value in drinking water by the United States Environmental Protection Agency (U.S. EPA) and the World Health Organization (WHO). The complex formation of N1 with Cu2+ was found to be 1:1 N1-Cu2+ by Job's plot analysis. Furthermore, the sensor was highly tolerant to interference from a matrix of real samples such as drinking water and human liver carcinoma cell line

Water-soluble Cu2+-fluorescent sensor based on core-substituted naphthalene diimide and its application in drinking water analysis and live cell imaging

Water-soluble naphthalene diimide based fluorescent chemosensor, N1, was designed for Cu2+ recognition. The sensor exhibited significant fluorescence modulation and chromogenic change with high Cu2+ sensitivity and selectivity over interfering metal ions. The sensor was able to efficiently monitor Cu2+ in 100% aqueous buffer solution with a low detection limit of 0.7 ppb which is much lower than the recommended value in drinking water by the United States Environmental Protection Agency (U.S. EPA) and the World Health Organization (WHO). The complex formation of N1 with Cu2+ was found to be 1:1 N1-Cu2+ by Job's plot analysis. Furthermore, the sensor was highly tolerant to interference from a matrix of real samples such as drinking water and human liver carcinoma cell line