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基于脱氢枞酸二芳胺的D-A-D型聚集诱导红光化合物的合成及其光谱性能

Synthesis and Spectral Properties of Dehydroabioic Acid Diarylamine-based D-A-D-type Aggregation-induced Red-light Compound

    摘要
  • 摘要: 以12-脱氢枞酸二芳胺为供体(D)，蒽醌基团为受体(A)，通过C-N偶联的方法合成D-A-D型化合物6,6′-((9,10-二氧代-9,10-二氢蒽-2,6-二基)双((4-甲氧基苯基)氮二基))双(7-异丙基-1,4-二甲基-1,2,3,4,4a,9,10,10-八氢蒽-1-羧酸酯)(2DDPA-AQ)，用核磁共振波谱和质谱表征其结构。测试2DDPA-AQ的紫外吸收光谱、荧光发射光谱、荧光量子产率及寿命、溶致变色效应、聚集诱导发光特性和抗光漂白特性；通过理论计算探讨其结构与性能间的关系。研究结果显示：2DDPA-AQ在甲苯中的最大紫外吸收波长为449 nm，在甲苯中和固体状态下的最大发射波长分别为630和653 nm，呈现红光发射；2DDPA-AQ在正己烷、环己烷、甲苯、二氧六环、四氢呋喃、乙酸乙酯中的最大荧光发射波长分别为578、584、630、638、645、650 nm。2DDPA-AQ的最大发射波长随溶剂极性的增大依次红移，表明其具有溶致变色效应和分子内的电荷转移行为。2DDPA-AQ的荧光发射强度随水/四氢呋喃(H2O/THF)中水体积分数的变化趋势表明其具有聚集诱导发光(AIE)特性；2DDPA-AQ在水体积分数为95%的H2O/THF中经连续30 min的紫外灯照射后，其荧光发射强度仅轻微减弱，表明其具有较强的抗光漂白特性。由实验所得数据计算2DDPA-AQ的HOMO/LUMO能级为-5.18 eV/-2.86 eV，带隙值为2.32 eV，按理论计算2DDPA-AQ的HOMO/LUMO能级为-4.91 eV/-2.14 eV，带隙值为2.77 eV，实验值与理论值略有偏差，由数据可知：2DDPA-AQ具有较窄带隙，符合红光分子的带隙特征。

     

    Abstract: 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.

     

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