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Excited State Intermolecular Proton Transfer Dependent on Substitution Pattern of Anthracene–Diurea Compounds involved in Fluorescent ON1–OFF–ON2 response by the Addition of Acetate Ions

Abstract

We report anthracene–diurea compounds allows us an anion sensor by using the fluorescence emission control depending on the substitution position on the anthracene ring. Anthracene–diurea compounds exhibit different excited-state intermolecular proton transfer (ESIPT) reactions depending on the pattern of the substituents. Three new anthracene–diurea compounds, which have two phenylurea groups substituted at different positions on anthracene, were synthesized. These compounds formed a complex with acetate ions through intermolecular hydrogen bonding between N–H and C=O moieties in the ground state. It was revealed that the difference in the position of the substituents greatly impacted the excited state intermolecular proton transfer. Whereas 1,5BPUA having the urea group at 1 and 5 positions exhibited ESIPT reaction, which is energetically favourable to form its tautomer, in the presence of TBAAc, 2,6BPUA having the urea group at low electron density positions, 2 and 6 positions, showed no ESIPT reaction due to the inversion of the LUMO energy levels of normal and tautomer states. As a result of detailed spectroscopic measurements, we found that the LUMO energy level of the normal form was lowered due to the urea group acting as an electron-withdrawing group. In addition, we revealed that 9,10BPUA had strong electronic interactions between the two phenylurea moieties at 9 and 10 positions, and caused an ON1–OFF–ON2 response for acetate ions. Our findings offer molecular design guidelines for the material having an anthracene moiety dependent on the substitution pattern of anthracene derivatives.

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Publication details

The article was received on 07 Jun 2017, accepted on 12 Jul 2017 and first published on 12 Jul 2017


Article type: Paper
DOI: 10.1039/C7OB01376K
Citation: Org. Biomol. Chem., 2017, Accepted Manuscript
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    Excited State Intermolecular Proton Transfer Dependent on Substitution Pattern of Anthracene–Diurea Compounds involved in Fluorescent ON1–OFF–ON2 response by the Addition of Acetate Ions

    H. Matsumoto, Y. Nishimura and T. Arai, Org. Biomol. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7OB01376K

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