Synthesis and energy transfer properties of fluorescence sensing bifluorophore based on 2-aminodimethylterephthalate and 3-aminobenzanthrone
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2018-01-01
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Abstract
New bifluorophore based on 2-aminodimethylterephthalate as a donor and 3-aminobenzanthrone as an acceptor of excitation energy was synthesized and characterized. The s-triazinyl ring as the spacer between two parts was used. A new monofluorophore 2-aminodimethylterephthalate derivative was synthesized as a reference compound and investigated as well. Absorption, emission spectra and fluorescence quantum yields of synthesized compounds were measured. Due to the efficient donor-acceptor energy transfer (89 %) the acceptor fluorescence of the system, excited in the maximal absorption of the donor fluorophore, was enhanced more than 5 times with respect to the fluorescence intensity of the reference 3-aminobenzanthrone. The sensor activity of mono and bifluorophore toward protons as cations and hydroxide as anions in DMF/water was studied by monitoring the changes of the fluorescence intensity. Due to internal charge transfer (ICT) at monofluorophore and the energy transfer (ET) at bifluorophore, the designed compounds were able to act as a pH-probe via an off-on fluorescence sensing mechanism.