Novel PDI-TPE Dyads For Anions/Cations Recognition

Perylene bisimide derivatives（PDI）have excellent optical,thermal and chemical stability and have been widely used in solar cells,organic light-emitting diodes and so on.Until now,most of the PDI reported derivatives bear single fluorophore,systems with other chromophores appending PDIs are still rare.In this thesis,we reported tetraphenylene（TPE）functionalized PDIs for metal ion and/or anion recognition.With perylenetetracarboxylic anhydride as the starting material,a series of PDI-TPE binary compounds with different spacers and anion/cantion recognition sites were synthesized.The spectral properties of the compounds and the ability of recognition different metal ions or anions were studied.The details are listed as follows:1.TPE functionalized PDIs at baysite and their metal ion recognition.A series of PDI-TPE binary compounds（2-1?2-4）linked with the triazole spacer at baysite of the PDI core were synthesized by click reaction.These compounds show PDI-based fluorescence emission with an aggregation-induced fluorescence enhancement（AIE）property.Interestingly,compounds 2-3 and 2-4 showed a good fluorescence response toward Hg²⁺.In the THF solution,the addition of Hg²⁺quenches the PDI-based emission of probes,with producing new bands attributed the TPE fluorophore.2.Novel PDI-TPE binarys contains triazolium donors for F^?recognition.On the basis of the second chapter,methylation the neutral receptors 2-1 and 2-3 resulted two triazolium compounds 3-1 and 3-2.Both receptors exhibit PDI-based fluorescence emission with a typical aggregation-induced fluorescence attenuation（ACQ）property.Interstion,probe 3-2 containing the amide NH donor and the triazolium（CH）⁺donors shows a good fluorescence recognition ability for F^-.The binding mechanism between host and guest was studied by ¹H NMR titration.3.The imide position modifies the synthesis of the triimidazolyl-containing PDI-TPE binary and its phosphate anion recognition.A new imidazole（CH）⁺and amide NH anion binding site perylenediimide-tetrastyrene binary 4-1 was synthesized and its ability to sense anions was investigated.The receptor molecule has an aggregation-induced fluorescence attenuating effect.In acetonitrile solution,it has a good fluorescence quenching response to H₂PO₄^?（Pi）and HP₂O₇^3?（PPi）.The probe has been successfully applied to the test paper to detect Pi and PPi,and can also distinguish Pi and other anions in the mixture of PPi and water-acetonitrile.