A cinnamoyl substituted Nile Red-based probe to detect hydrazine. Issue 24 (14th June 2017)

• Record Type: Journal Article
• Authors: Jiang, Xin-Dong; Guan, Jian; Bian, Hui; Xiao, Yi
• Is Part Of: Tetrahedron letters. Volume 58:Issue 24(2017)
• Page Start: 2351
• Page End: 2354
• Publication Date: 2017-06-14
• Subjects: Hydrazine -- Hydrazinolysis -- Cinnamoyl -- π-π conjugate; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.05.003
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Nile Red-based probe with a new recognition unit (cinnamoyl) was highly selective and sensitive to N2 H4 . Because the combination of the π-π conjugate system can stabilize the ethylene union, the nucleophilic addition of the thiol group of Cys/Hcy becomes non-effective. Highlights: Nile Red-based probe with a new recognition unit (cinnamoyl) was highly selective and sensitive to N2 H4 . The combination of the π-π conjugate system can stabilize the ethylene union. The nucleophilic addition of the thiol group of Cys/Hcy becomes non-effective. Hydrazinolysis by N2 H4 generated Nile Red derivative was advocated and feasible. Abstract: Herein we discovered that a Nile Red-based probe with a cinnamoyl unit was highly selective and sensitive to N2 H4 . Hydrazinolysis by N2 H4 would release a hydroxyl substituted Nile Red and result in remarkable fluorescence quench. Importantly, Cys/Hcy would not interrupt the N2 H4 recognition. This is because, for this probe, the combination of the π-π conjugate system can stabilize the ethylene union, which results in the nucleophilic addition of the thiol group of Cys/Hcy becomes non-effective.