Bifunctional fluorescent quenching detection of 2, 4, 6-trinitrophenol (TNP) and acetate ions via 4, 4′-(9, 9-dimethyl-9H-fluorene-2, 7-diyl)dibenzoic acid. Issue 45 (9th November 2016)

• Record Type: Journal Article
• Authors: Ni, Jue Chen; Yan, Jie; Zhang, Li Jing; Shang, Di; Du, Ning; Li, Shuang; Zhao, Jin Xin; Wang, Yang; Xing, Yong Heng
• Is Part Of: Tetrahedron letters. Volume 57:Issue 45(2016)
• Page Start: 4978
• Page End: 4982
• Publication Date: 2016-11-09
• Subjects: Fluorescence sensor -- Synthesis -- Suzuki coupling -- Nitroaromatic compounds -- Anions; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.09.089
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: We developed a novel pathway to synthesize fluorene derivatives (compound4 ). The single crystal of new intermediate3 was obtained by Suzuki coupling reaction. We examined the emission spectrum of the fluorene and compounds1 –5 . New experiment was firstly carried out about sensing of NACs and anions based on5 . We discussed the quenching mechanism based on the effects of π–π interaction. Abstract: The 4, 4′-(9, 9-dimethylfluorene-2, 7-diyl)dibenzoic acid (5 ) was synthesized using commercial fluorene as the starting material followed by processes of bromination, methylation, Suzuki coupling and hydrolysis. We reported it as an exclusive fluorescence sensor for 2, 4, 6-trinitrophenol (TNP) and acetate ions for the first time. The experimental results suggested a high efficiency for TNP detection with K SV values of 21, 215 M −1, which has achieved to micromolar level (10 μM) of this material. Moreover, the detection limit (1.39 × 10 −6 M) was measured according to the fluorescence intensity changes of Ac − in CH3 CN.