水溶性共轭聚合物的设计、合成与生物传感研究
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摘要
本论文围绕水溶性共轭聚合物的设计、合成及其在化学与生物识别及传感中的应用,开展了以下几个方面的研究工作:
(一)利用Suzuki偶联反应合成了侧链带咪唑功能团的水溶性阳离子聚芴(CCP1),用元素分析,质谱,核磁共振光谱,红外光谱,GPC对其结构进行了确认和表征;利用紫外与荧光光谱(UV和FL)对聚合物的光物理性质进行了表征。发展了一种新型基于CCP1的一氧化氮(NO)检测方法,该体系由三部分组成: CCP1、二价铜离子(Cu~(2+))和NO。Cu~(2+)通过N-Cu相互作用与聚芴结合,通过光诱导的电子转移过程将聚芴的荧光有效的淬灭。加入NO后,NO将顺磁性的Cu~(2+)转变成抗磁性的Cu1+,禁止了对聚合物荧光的淬灭,聚合物CCP1的荧光恢复。在相同的条件下,其他相关的干扰化合物,如NOBF4、NaNO2和NaNO3都不能使顺磁性的Cu~(2+)转变成抗磁性的Cu1+,所以CCP1的荧光也不能恢复。此种检测方法操作简单、分析快速,可以实现在水体系中对NO高灵敏度和高选择性的检测。
(二)设计合成了主链含有2,2’-联吡啶的一系列水溶性阳离子聚芴衍生物(PFP-P1-3),用元素分析,质谱,核磁共振光谱,红外光谱,GPC对化合物的结构进行了确认和表征;利用紫外与荧光光谱(UV和FL)对聚合物的光物理性质进行了表征。其中PFP-P2可以作为一种高灵敏度和选择性的荧光探针成功实现了在水体系中对二价铜离子(Cu~(2+))的检测。无Cu~(2+)存在时,PFP-P2在水溶液中发出很强的荧光;加入Cu~(2+)后,PFP-P2就会通过N…Cu相互作用与Cu~(2+)络和,荧光被高效地淬灭。通过PFP-P荧光强度的变化可实现Cu~(2+)的检测。该方法具有水相检测、简单快速、高灵敏度和选择性的优点。
(三)设计合成了同时带有正电荷和负电荷的水溶性寡聚芴分子(OF1),通过荧光发射光谱研究了OF1在Fe(CN)64-作用下的荧光淬灭性质以及其与荧光素标记的DNA之间的荧光共振能量转移(FRET)性质。由于存在较强的分子间相互作用,OF1表现出同共轭聚合物相似的光吸收能力,可成倍放大荧光信号。
A series of water-soluble conjugated polyfluorenes were designed and synthesized. Highly sensitive and selective chemosensors and biosensors were developed using these conjugated polymers as optical probes. The results are summarized as follows: 1. The water-soluble cationic polyfluorene (CCP1) containing the imidazole moieties in side chain was designed and synthesized as the fluorescent probe for“turn-on”detection of nitric oxide (NO). The assay benefits from the sensitivity of optical signals from conjugated polymers and the simplicity of fluorescence measurement techniques. The assay contains three elements: a cationic conjugated polymer containing imidazole moieties, Cu~(2+) ions, and the target nitric oxide. The highly fluorescent conjugated polymer coordinates to Cu~(2+) ions through weak N…Cu interactions, and its fluorescence is efficiently quenched via photo-induced electron transfer process (‘off’state). In the presence of nitric oxide, the transformation of the paramagnetic Cu~(2+) ion into diamagnetic Cu1+ ion inhibits the quenching and therefore the fluorescence of the conjugate polymer is recovered (‘on’state). Other biologically relevant reactive nitrogen species, such as NOBF4, NaNO2 and NaNO3 don’t exhibit the fluorescence recovery of conjugated polymer in the same condition as nitric oxide. The cationic conjugated polymer/Cu~(2+) complex can thus be used as the platform to detect nitric oxide in aqueous solution with high sensitivity and selectivity.
2. We design and synthesize a new series of water-soluble cationic polyfluorene copolymers containing 2,2’-bipyridyl-phenylene-vinylene moieties in the backbone (PFP-P1-3). Among them, PFP-P2 can be used as selective and sensitive fluorescent probe to detect Cu~(2+) ions in aqueous medium. In the absence of the Cu~(2+) ion, the PFP-P2 exhibits strong fluorescence emission in aqueous solution. Upon adding the Cu~(2+) ion, the PFP-P coordinates to Cu~(2+) ions through weak N…Cu interactions, and its fluorescence is efficiently quenched by the Cu~(2+) ion. By triggering the change of emission intensity of PFP-P, it is suitable to assay Cu~(2+) ions in aqueous solution. The assay benefits from the sensitivity of optical signals from conjugated polymers and the simplicity of fluorescence measurement techniques.
3. Water-soluble cationic oligofluorene containing one carboxyl group on side chain (OF1) was synthesized by Suzuki coupling. The presence of terminal ammonium moieties and carboxyl group increases intermolecular electrostatic interactions. The electrostatic forces and hydrophobic interactions lead to the formation of polymeric-like structures for OF 1, which offers it similar light-harvesting ability as that of cationic conjugated polyelectrolytes. This collective optical behavior was studied by fluorescence quenching experiments and fluorescence resonance energy transfer (FRET) experiments with fluorescein-labeled double-stranded DNA (dsDNA-F1).
(一)利用Suzuki偶联反应合成了侧链带咪唑功能团的水溶性阳离子聚芴(CCP1),用元素分析,质谱,核磁共振光谱,红外光谱,GPC对其结构进行了确认和表征;利用紫外与荧光光谱(UV和FL)对聚合物的光物理性质进行了表征。发展了一种新型基于CCP1的一氧化氮(NO)检测方法,该体系由三部分组成: CCP1、二价铜离子(Cu~(2+))和NO。Cu~(2+)通过N-Cu相互作用与聚芴结合,通过光诱导的电子转移过程将聚芴的荧光有效的淬灭。加入NO后,NO将顺磁性的Cu~(2+)转变成抗磁性的Cu1+,禁止了对聚合物荧光的淬灭,聚合物CCP1的荧光恢复。在相同的条件下,其他相关的干扰化合物,如NOBF4、NaNO2和NaNO3都不能使顺磁性的Cu~(2+)转变成抗磁性的Cu1+,所以CCP1的荧光也不能恢复。此种检测方法操作简单、分析快速,可以实现在水体系中对NO高灵敏度和高选择性的检测。
(二)设计合成了主链含有2,2’-联吡啶的一系列水溶性阳离子聚芴衍生物(PFP-P1-3),用元素分析,质谱,核磁共振光谱,红外光谱,GPC对化合物的结构进行了确认和表征;利用紫外与荧光光谱(UV和FL)对聚合物的光物理性质进行了表征。其中PFP-P2可以作为一种高灵敏度和选择性的荧光探针成功实现了在水体系中对二价铜离子(Cu~(2+))的检测。无Cu~(2+)存在时,PFP-P2在水溶液中发出很强的荧光;加入Cu~(2+)后,PFP-P2就会通过N…Cu相互作用与Cu~(2+)络和,荧光被高效地淬灭。通过PFP-P荧光强度的变化可实现Cu~(2+)的检测。该方法具有水相检测、简单快速、高灵敏度和选择性的优点。
(三)设计合成了同时带有正电荷和负电荷的水溶性寡聚芴分子(OF1),通过荧光发射光谱研究了OF1在Fe(CN)64-作用下的荧光淬灭性质以及其与荧光素标记的DNA之间的荧光共振能量转移(FRET)性质。由于存在较强的分子间相互作用,OF1表现出同共轭聚合物相似的光吸收能力,可成倍放大荧光信号。
A series of water-soluble conjugated polyfluorenes were designed and synthesized. Highly sensitive and selective chemosensors and biosensors were developed using these conjugated polymers as optical probes. The results are summarized as follows: 1. The water-soluble cationic polyfluorene (CCP1) containing the imidazole moieties in side chain was designed and synthesized as the fluorescent probe for“turn-on”detection of nitric oxide (NO). The assay benefits from the sensitivity of optical signals from conjugated polymers and the simplicity of fluorescence measurement techniques. The assay contains three elements: a cationic conjugated polymer containing imidazole moieties, Cu~(2+) ions, and the target nitric oxide. The highly fluorescent conjugated polymer coordinates to Cu~(2+) ions through weak N…Cu interactions, and its fluorescence is efficiently quenched via photo-induced electron transfer process (‘off’state). In the presence of nitric oxide, the transformation of the paramagnetic Cu~(2+) ion into diamagnetic Cu1+ ion inhibits the quenching and therefore the fluorescence of the conjugate polymer is recovered (‘on’state). Other biologically relevant reactive nitrogen species, such as NOBF4, NaNO2 and NaNO3 don’t exhibit the fluorescence recovery of conjugated polymer in the same condition as nitric oxide. The cationic conjugated polymer/Cu~(2+) complex can thus be used as the platform to detect nitric oxide in aqueous solution with high sensitivity and selectivity.
2. We design and synthesize a new series of water-soluble cationic polyfluorene copolymers containing 2,2’-bipyridyl-phenylene-vinylene moieties in the backbone (PFP-P1-3). Among them, PFP-P2 can be used as selective and sensitive fluorescent probe to detect Cu~(2+) ions in aqueous medium. In the absence of the Cu~(2+) ion, the PFP-P2 exhibits strong fluorescence emission in aqueous solution. Upon adding the Cu~(2+) ion, the PFP-P coordinates to Cu~(2+) ions through weak N…Cu interactions, and its fluorescence is efficiently quenched by the Cu~(2+) ion. By triggering the change of emission intensity of PFP-P, it is suitable to assay Cu~(2+) ions in aqueous solution. The assay benefits from the sensitivity of optical signals from conjugated polymers and the simplicity of fluorescence measurement techniques.
3. Water-soluble cationic oligofluorene containing one carboxyl group on side chain (OF1) was synthesized by Suzuki coupling. The presence of terminal ammonium moieties and carboxyl group increases intermolecular electrostatic interactions. The electrostatic forces and hydrophobic interactions lead to the formation of polymeric-like structures for OF 1, which offers it similar light-harvesting ability as that of cationic conjugated polyelectrolytes. This collective optical behavior was studied by fluorescence quenching experiments and fluorescence resonance energy transfer (FRET) experiments with fluorescein-labeled double-stranded DNA (dsDNA-F1).
引文
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