吡啶盐类化合物的合成及其碳纳米复合材料的光学性质研究
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摘要
近20年来,碳纳米材料受到人们的广泛关注,与有机染料复合,研究其光学性质,探讨其在荧光探针、离子识别、生物显影等方面的应用具有重要的科学意义。
1、本文基于蒽类衍生物良好的光学性质,以9-氯甲基蒽为母体,采用Knoevenagel反应合成了一系列功能化的蒽吡啶盐衍生物Y1-Y4,通过核磁共振氢谱、核磁共振碳谱、质谱、红外光谱等分析手段表征了它们的结构和组成,研究了该系列染料分子内FRET过程,发现以蒽为荧光给体,吡啶盐为荧光受体的FRET过程是一种不完全的FRET过程,使整个分子在荧光光谱上呈现双荧光。
2、通过电化学方法合成了一种碳量子点,通过NaBH4还原进行表面功能化,还原后的碳量子点发射峰蓝移,发光增强。将碳量子点与染料复合,以Y2作为能量给体而碳量子点作为能量受体时,FRET过程没有发生,而染料的发射峰随着量子点浓度增大,呈现线性增强。当以Y2,Y4作为能量受体而碳量子点作为能量给体时,发生FRET过程。这是由于碳量子点的加入,染料分子内的能量转移过程被阻隔。因此,在碳量子点／有机染料复合体系中,碳量子点作为能量给体,更易发生FRET过程。
3、将Y1-Y4与环糊精复合,研究两者之间的主客体化学,发现环糊精与这一系列染料都存在缔合或包合作用,使染料荧光发生不同程度的增强,Y3,Y4的发射峰发生蓝移。而环糊精与蒽的作用明显不如与吡啶盐基团的作用力强。
4、将Y1-Y4与石墨烯复合,发现能量由蒽或吡啶盐向石墨烯转移,使得自身荧光不断淬灭,而石墨烯阻止了Y1-Y4分子内由蒽向吡啶盐基团的FRET过程。
5、以对苯二乙腈和对[(N-甲基N-羟乙基)胺基]苯甲醛为原料,通过Knoevenagel反应合成了一种具有AIEE效应的化合物NOCN,并与己内脂等聚合。在THF-水混合溶剂中,NOCN随着水的比例增加,最大荧光发射峰从515nm到581nm发生的明显红移,而固体最大荧光发射峰在627nm；而NOCN的聚集体NOCN3,随着水的比例增加,最大荧光发射峰位置不变,而发光强度逐渐增强,体现出AIEE效应。当将NOCN与NOCN3分别与碳量子点复合后,碳量子点都体现出良好的能量给体性质,使NOCN或NOCN3在THF中荧光都得到不同程度的增强,而在水中这种能量转移过程较弱。
In recent20years, carbon nano-materials have drawn extensive attentions. The study on their photoluminescent properties is of an important scientific meaning in the applications for fluorescent probe, ion recognition, biological imaging and so on.
1. In this dissertation, a series of organic dyes Y1-Y4from9-chlorinemethyl anthracene were designed relying on the good optical properties of anthracene, which were synthesized by Knoevenagel reaction and characterized by1H NMR,13C NMR and IR spectra. The FRET process of Y1-Y4was studied by PL spectra. It was found that the molecules, in which anthracene group acts as a donor and the pyridinium group acts as a acceptor, exhibit an incomplete fluorescence resonance energy transfer (FRET) process.
2. Water soluble fluorescent carbon dots were synthesized by electrochemical method. The carbon dots were functionalized on the surface using NaBH4, which emit enhanced blue-shift fluorescence. No fluorescence resonance energy transfer took place for the hybrid, in which carbon dots act as a acceptor and Y2acts as a donor. However, the intensity of the fluorescence increased. While the FRET process take place when the carbon dots acts as a donor, and Y2acts as a acceptor. The energy transfer is observed from carbon dots toY2and Y4. So it is concluded that fluorescence resonance energy transfer takes place more easily for the hybrid system, when carbon dots act as a donor.
3. When Y1-Y4was included with cyclodextrin to form complexes, which were studied based on principle of the host-guest chemistry. It was found that there is an inclusion process between the dyes and cyclodextrin. The enhanced fluorescence was observed for the complexes. The cylodextrin had a stronger interaction with pyridinium group than that of anthracene group.
4. When Y1-Y4combine with grapheme. It was found that the energy transfer takes place from the anthracene or pyridinium groups to grapheme. The fluorescence was quenched for hybrid system, and the graphene block the intramolecular FRET process.
5. A new compound NOCN bearing AIEE effect was synthesized through the Knoevenagel reaction, using1,4-Phenylenediacetonitrile and p-[(N-Methyl-N-hydroxyethyl)amino] benzaldehyde as starting materials. The fluorescence emission maxima exhibited a bathochromic shift from515to581nm when the ratio of H2O increases in THF/H2O mixed solvents, while emission at627nm in solid state. However, the wavelength of the fluorescence emission exhibits unchanged, while the intensity increased when the ratio of H2O increases in THF/H2O mixed solvents for the aggregation of NOCN3. When NOCN and NOCN3combined with carbon dots, the FRET process existed in both THF and H2O solvents. Although, this energy transfer process was weaker in the water than that in THF.
1、本文基于蒽类衍生物良好的光学性质,以9-氯甲基蒽为母体,采用Knoevenagel反应合成了一系列功能化的蒽吡啶盐衍生物Y1-Y4,通过核磁共振氢谱、核磁共振碳谱、质谱、红外光谱等分析手段表征了它们的结构和组成,研究了该系列染料分子内FRET过程,发现以蒽为荧光给体,吡啶盐为荧光受体的FRET过程是一种不完全的FRET过程,使整个分子在荧光光谱上呈现双荧光。
2、通过电化学方法合成了一种碳量子点,通过NaBH4还原进行表面功能化,还原后的碳量子点发射峰蓝移,发光增强。将碳量子点与染料复合,以Y2作为能量给体而碳量子点作为能量受体时,FRET过程没有发生,而染料的发射峰随着量子点浓度增大,呈现线性增强。当以Y2,Y4作为能量受体而碳量子点作为能量给体时,发生FRET过程。这是由于碳量子点的加入,染料分子内的能量转移过程被阻隔。因此,在碳量子点／有机染料复合体系中,碳量子点作为能量给体,更易发生FRET过程。
3、将Y1-Y4与环糊精复合,研究两者之间的主客体化学,发现环糊精与这一系列染料都存在缔合或包合作用,使染料荧光发生不同程度的增强,Y3,Y4的发射峰发生蓝移。而环糊精与蒽的作用明显不如与吡啶盐基团的作用力强。
4、将Y1-Y4与石墨烯复合,发现能量由蒽或吡啶盐向石墨烯转移,使得自身荧光不断淬灭,而石墨烯阻止了Y1-Y4分子内由蒽向吡啶盐基团的FRET过程。
5、以对苯二乙腈和对[(N-甲基N-羟乙基)胺基]苯甲醛为原料,通过Knoevenagel反应合成了一种具有AIEE效应的化合物NOCN,并与己内脂等聚合。在THF-水混合溶剂中,NOCN随着水的比例增加,最大荧光发射峰从515nm到581nm发生的明显红移,而固体最大荧光发射峰在627nm；而NOCN的聚集体NOCN3,随着水的比例增加,最大荧光发射峰位置不变,而发光强度逐渐增强,体现出AIEE效应。当将NOCN与NOCN3分别与碳量子点复合后,碳量子点都体现出良好的能量给体性质,使NOCN或NOCN3在THF中荧光都得到不同程度的增强,而在水中这种能量转移过程较弱。
In recent20years, carbon nano-materials have drawn extensive attentions. The study on their photoluminescent properties is of an important scientific meaning in the applications for fluorescent probe, ion recognition, biological imaging and so on.
1. In this dissertation, a series of organic dyes Y1-Y4from9-chlorinemethyl anthracene were designed relying on the good optical properties of anthracene, which were synthesized by Knoevenagel reaction and characterized by1H NMR,13C NMR and IR spectra. The FRET process of Y1-Y4was studied by PL spectra. It was found that the molecules, in which anthracene group acts as a donor and the pyridinium group acts as a acceptor, exhibit an incomplete fluorescence resonance energy transfer (FRET) process.
2. Water soluble fluorescent carbon dots were synthesized by electrochemical method. The carbon dots were functionalized on the surface using NaBH4, which emit enhanced blue-shift fluorescence. No fluorescence resonance energy transfer took place for the hybrid, in which carbon dots act as a acceptor and Y2acts as a donor. However, the intensity of the fluorescence increased. While the FRET process take place when the carbon dots acts as a donor, and Y2acts as a acceptor. The energy transfer is observed from carbon dots toY2and Y4. So it is concluded that fluorescence resonance energy transfer takes place more easily for the hybrid system, when carbon dots act as a donor.
3. When Y1-Y4was included with cyclodextrin to form complexes, which were studied based on principle of the host-guest chemistry. It was found that there is an inclusion process between the dyes and cyclodextrin. The enhanced fluorescence was observed for the complexes. The cylodextrin had a stronger interaction with pyridinium group than that of anthracene group.
4. When Y1-Y4combine with grapheme. It was found that the energy transfer takes place from the anthracene or pyridinium groups to grapheme. The fluorescence was quenched for hybrid system, and the graphene block the intramolecular FRET process.
5. A new compound NOCN bearing AIEE effect was synthesized through the Knoevenagel reaction, using1,4-Phenylenediacetonitrile and p-[(N-Methyl-N-hydroxyethyl)amino] benzaldehyde as starting materials. The fluorescence emission maxima exhibited a bathochromic shift from515to581nm when the ratio of H2O increases in THF/H2O mixed solvents, while emission at627nm in solid state. However, the wavelength of the fluorescence emission exhibits unchanged, while the intensity increased when the ratio of H2O increases in THF/H2O mixed solvents for the aggregation of NOCN3. When NOCN and NOCN3combined with carbon dots, the FRET process existed in both THF and H2O solvents. Although, this energy transfer process was weaker in the water than that in THF.
引文
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