Synthesis and Spectral Properties of Dehydroabioic Acid Diarylamine-based D-A-D-type Aggregation-induced Red-light Compound
A D-A-D-type compound named 6,6'-((9,10-dioxo-9,10-dihydroanth-racene-2,6-diyl)bis((4-methoxyphenyl)azanediyl))bis(7-isopropyl-1,4-dimethyl-1,2,3,4,4a,9,10,10a-octah-ydrophenanthr-ene-1-carboxylate)(2DDPA-AQ)was synthesized using 12-dehydroabietic acid diarylamine as the donor(D)and anthraquinone group as the acceptor(A),and its structure was characterized by the NMR and MS.The UV-Vis absorption and the fluorescence emission spectrum,the fluorescence quantum yield and lifetime,solvatochromic effect,aggregation-induced luminescence and photobleaching resistance characteristics were tested.The theoretical calculation was used to analyze the relationship between its structure and properties.The research results were as follows:the maximum ultraviolet absorption wavelength of 2DDPA-AQ in toluene was 449 nm,while the maximum emission wavelengths in toluene and solid state were 630 and 653 nm,showing red light emission.The maximum fluorescence emission wavelengths of 2DDPA-AQ in n-hexane,cyclohexane,toluene,dioxane,tetrahydrofuran,and ethyl acetate were 578,584,630,638,645,and 650 nm,respectively.The red shift of the maximum emission wavelength of 2DDPA-AQ along with the increase of the polarity of the solvent showed that it had solvatochromism effect and intramolecular charge transfer behaviour.The variation trend of fluorescence emission intensity of 2DDPA-AQ with water volume fraction in water/tetrahydrofuran(H2O/THF)indicated its aggregation induced emission(AIE)characteristics.After continuous 30 minutes of UV lamp irradiation in a H2O/THF mixed solution with water volume fraction of 95％,the fluorescence emission intensity of 2DDPA-AQ only slightly weakened,indicating its strong anti-photobleaching properties.Based on the experimental data,the HOMO/LUMO energy level of 2DDPA-AQ was-5.18 eV/-2.86 eV with a bandgap value of 2.32 eV.The theoretically calculated HOMO/LUMO energy level was-4.91 eV/2.14 eV with a bandgap value of 2.77 eV.The data showed that 2DDPA-AQ had a relatively narrow bandgap,which was consistent with the bandgap characteristics of red light molecules.
ehydroabiotic acid diarylamineanthraquinoneD-A-D typeaggregation-induced red light emission
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