Synthesis, Aggregation-Induced Emission and Circularly Polarized Luminescence of Poly(3, 3'-bicarbazolylterephthalonitrile) with Chiral Binaphthalene Pendant Groups
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摘要: 以手性联二萘(BINOL)取代的2, 3-二氟对苯二腈和3, 3'-联咔唑为单体，通过碳-氮偶联反应得到一对共轭聚合物(R)-P1和(S)-P1，并且通过1H NMR与13C NMR、凝胶渗透色谱(GPC)、热重分析(TGA)、荧光发射光谱(PL)、圆二色谱(CD)和圆偏振发光(CPL)光谱等对聚合物的化学结构、分子量、热稳定性以及光物理性质等进行了表征.结果表明：该聚合物具有明显的聚集诱导发光(AIE)性质；手性联二萘侧基能有效地诱导共轭主链的微环境，使该聚合物具有手性活性，且表现出CPL特性.Abstract: A couple of conjugated polymers (R)-P1 and (S)-P1 were synthesized using chiral Binaphthalene (BINOL) substituted 2, 3-tetrafluoroterephthalonitrile and 3, 3'-bicarbazole as the monomers via C-N coupling reaction. The chemical structures and properties of the polymers were characterized with 1H NMR, 13C NMR, gel permeation chromatography (GPC), thermogravimetric analysis (TGA) as well as PL spectra, circular dichroism(CD) and circularly polarized luminescence (CPL) spectra. The experimental results suggested that the obtained polymers were aggregation-induced emission (AIE) and CPL active, manifesting the chirality transmission from 1, 1'-binaphthalenependant groups to the conjugated main chain.
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图 2 (R)-P1、(S)-P1在二氧六环溶液中的紫外-可见吸收光谱(a、b)、荧光发射光谱(c、d)以及(R)-P1、(S)-P1粉末的荧光发射光谱(e、f)
注：溶液中(R)-P1、(S)-P1的浓度为10 μmol/L.荧光发射光谱测试的激发波长为330 nm.
Figure 2. The UV-Visible absorption (a, b) and PL (c, d) spectra of (R)-P1 and (S)-P1 in dioxane and the PL spectra (e, f) of (R)-P1 and (S)-P1 powders
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图 3 (R)-P1和(S)-P1在不同极性溶剂中的紫外-可见吸收光谱及荧光发射光谱
注：(R)-P1和(S)-P1的浓度为10 μmol/L.
Figure 3. The UV-Visible absorption and PL spectra of (R)-1 and (S)-1 in solutions with different polarities
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图 4 不同极性溶剂中(R)-P1和(S)-P1在365 nm波长紫外光照射下的荧光照片
注：溶剂ToL、TCM、THF、EA和ACN分别为甲苯、氯仿、四氢呋喃、乙酸乙酯和乙腈.
Figure 4. The emission images of (R)-P1 and (S)-P1 in solutions with different polarities under the illumination of 365 nm UV light
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图 5 (R)-P1和(S)-P1在不同w(H2O)的水/四氢呋喃混合溶液中的荧光发射光谱
注：(R)-P1和(S)-P1的浓度为10 μmol/L; 测试的激发波长为340 nm.插图是365 nm紫外光激发下，w(H2O)分别为0%和95%的混合溶液的荧光照片.
Figure 5. The PL spectra of the dilute solutions of (R)-P1 and (S)-P1 in water/THF mixtures with different w(H2O) values
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图 6 (R)-P1和(S)-P1在不同含水质量分数的水/四氢呋喃混合溶液中的紫外-可见吸收光谱
注：(R)-P1和(S)-P1的浓度为10 μmol/L.
Figure 6. The UV-Visible absorption spectra of the dilute solutions of (R)-P1 and (S)-P1 in water/THF mixtures with different water fractions
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图 7 (R)-P1和(S)-P1在w(H2O)为95%的水/四氢呋喃混合溶液中的粒径分布
注：(R)-P1和(S)-P1的浓度为10 μmol/L.
Figure 7. The effective diameters of the nanoparticles of (R)-P1 and (S)-P1 in water/THF mixtures with 95% water fraction
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