Revisit of a series of ICT fluorophores: skeletal characterization,structural modification,and spectroscopic behavior |
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| Authors: | Honglin Li Fengyu Liu Yi Xiao Perry J. Pellechia Mark D. Smith Xuhong Qian Guiren Wang Qian Wang |
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| Affiliation: | 1. Department of Chemistry and Biochemistry, University of South Carolina, 631 Sumter Street, Columbia, SC 29208, USA;2. School of Chemistry, Dalian University of Technology, Dalian 116024, China;3. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China;4. Shanghai Key Laboratory of Chemical Biology, Institute of Pesticides and Pharmaceuticals, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China;5. Department of Mechanical Engineering & Biomedical Engineering Program, University of South Carolina, 300 Main Street, Columbia, SC 29208, USA |
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| Abstract: | We have revisited the synthesis of a series of ICT fluorophores, which were reported to have a core structure of 8-oxo-8H-acenaphtho[1,2-b]pyrrol-9-carbonitrile. However, based on the 2D NMR and X-ray diffraction analysis, their core structure was corrected as 1-oxo-1H-phenalene-2,3-dicarbonitrile (1). Compound 1 shows a highly electron-deficient nature and can easily undergo oxidative SNArH reaction on the naphthyl ring to produce a series of novel ICT fluorophores. The regioselectivity of this substitution reaction was studied by introduction of representative nucleophiles. Moreover, due to the strong rigidity and efficient ICT nature, the obtained fluorescent dyes display very good spectroscopic properties even in an aqueous environment. |
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| Keywords: | ICT fluorophore Skeletal characterization Oxidative SNArH 2D NMR X-ray diffraction |
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