二芳基乙烯分子开关及其金属配合物的设计、合成与性能研究
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摘要
近年来,分子电子器件(如分子场效应管、分子整流器、分子储存器、分子导线、分子开关和分子马达等)作为下一代电子器件得到了快速的发展。其中,分子开关作为未来逻辑和存储电路的基本单元而备受人们的关注。在各种分子开关体系中,二芳基乙烯化合物由于其良好的热稳定性和优秀的抗疲劳性而成为最有应用前景的光致变色化合物之一。因此,发展结构新颖、性能独特的二芳基乙烯化合物具有重要的意义。在本论文中,我们分别从取代基效应、溶剂效应、酸碱效应及金属配位效应对2-(2-吡啶)咪唑类的二芳基乙烯化合物(PI-BTEs)荧光和光致变色性能的影响进行了系统的研究。主要的研究内容如下：
1、为研究不同取代基对2-(2-吡啶)咪唑类的二芳基乙烯化合物(PI-BTEs)荧光和光致变色性能的影响,我们设计合成了一系列二芳基乙烯化合物L1-L5,同时我们也研究了溶剂效应对母体化合物L3荧光和光致变色性能的影响。这些研究结果将为我们今后根据需要来设计新型的PI-BTEs化合物提供一定的借鉴和指导。
2、由于碱性基团(咪唑和吡啶)和酸能发生酸碱作用,因此,我们设计合成了一系列以咪唑为烯桥的二芳基乙烯化合物L2、L3、L6及L7来研究酸对它们吸收光谱、荧光光谱和热稳定性的影响。研究结果显示,在酸的诱导下,我们不仅能实现咪唑二芳基乙烯化合物在P型光致变色和T型光致变色之间相互切换(这种光致变色化合物在光写-热擦的可再写纸领域有潜在的应用)；而且通过调节酸的量,我们还能够对咪唑二芳基乙烯化合物的光致变色性能实现可逆的酸致门控“锁”的调控。在这个过程中,强酸起着门控“锁”的作用,而碱性的三乙胺则起着门控“钥匙”的作用。这种门控光致变色在数据无损读取方面有潜在的应用。
3、通过2-(2-吡啶)咪唑与金属砌块的螯合作用,我们设计合成了铂金属配合物L2-Pt和L4-Pt。研究结果显示,配合物L2-Pt不仅展示了良好的近红外的光致变色性能,而且还展示了荧光“turn on”的性能。据我们所知,这是第一例荧光“turn on”且近红外光致变色的金属二芳基乙烯分子开关,这种分子开关在高分辨荧光成像和生物荧光标签方面具有潜在的应用价值。
In recent years, molecular electronic devices (such as molecular field effect tube, molecular rectifier, molecular memory, molecular wire, molecular switch and molecular motor, etc.) as the next generation of electronic devices have been rapid development. Among them, the molecular switch as the basic unit of future logic and storage circuit has attracted much attention. Among the various molecular switch systems, diarylethenes, due to their excellent thermal stability and outstanding fatigue resistance, are one of the most promising photochromic compounds for practical applications. Therefore, it is very significant to develop the diarylethenes with novel structures and unique performances. In this thesis, we systematically studied the substituent effects, solvent effects, acid-base effect and metal complexing effect on the fluorescent and photochromic properties of2-(2-pyridyl) imidazole containing diarylethene derivatives (PI-BTEs). The main research contents are as follows:
1. For studying the different substituents on the fluorescent and photochromic performances of2-(2-pyridyl) imidazole containing diarylethene derivatives (PI-BTEs), we designed to synthesize a series of diarylethene compounds L1-L5, and studied the solvent effect of the parent compound L3on the fluorescence and photochromic properties. The results would provide some reference and guidance for us to design novel PI-BTEs compounds according to the requirement in future.
2. Because of the acid-base interaction between the alkaline groups (imidazole and pyridine) and the acid, a series of diarylethene derivatives with imidazoles as the ethene bridges (L2, L3, L6and L7) are prepared to investigate the influence on their absorption spectra, fluorescence spectra and thermal stability by the acid. It has been demonstrated that not only switch of the diarylethene derivatives between P-type and T-type photochromism by the acid stimuli (this photochromic compound has a potential application in rewritable papers of write-by light/erase-by-heat systems) is achieved, but also the reversible acid induced gating "lock" regulation by adjusting the quantity of acid is accomplished. The strong acid plays a gated "lock" role and the alkaline triethylamine may act as the "key" role in this process. Such gating photochromism has potential applications in nondestructive readout.
3. By chelating metallic subunits with2-(2-pyridyl) imidazole, we designed to synthesize the platinum complexes of L2-Pt and L4-Pt. The results show that L2-Pt complex exhibits not only the near-infrared photochromism but also the turn-on fluorescence. To the best of our knowledge, this is the first turn-on fluorescence and near-infrared photochromism of metal diarylethene molecular switch, which has potential applications in the high resolution fluorescence imaging and biological fluorescence label.
1、为研究不同取代基对2-(2-吡啶)咪唑类的二芳基乙烯化合物(PI-BTEs)荧光和光致变色性能的影响,我们设计合成了一系列二芳基乙烯化合物L1-L5,同时我们也研究了溶剂效应对母体化合物L3荧光和光致变色性能的影响。这些研究结果将为我们今后根据需要来设计新型的PI-BTEs化合物提供一定的借鉴和指导。
2、由于碱性基团(咪唑和吡啶)和酸能发生酸碱作用,因此,我们设计合成了一系列以咪唑为烯桥的二芳基乙烯化合物L2、L3、L6及L7来研究酸对它们吸收光谱、荧光光谱和热稳定性的影响。研究结果显示,在酸的诱导下,我们不仅能实现咪唑二芳基乙烯化合物在P型光致变色和T型光致变色之间相互切换(这种光致变色化合物在光写-热擦的可再写纸领域有潜在的应用)；而且通过调节酸的量,我们还能够对咪唑二芳基乙烯化合物的光致变色性能实现可逆的酸致门控“锁”的调控。在这个过程中,强酸起着门控“锁”的作用,而碱性的三乙胺则起着门控“钥匙”的作用。这种门控光致变色在数据无损读取方面有潜在的应用。
3、通过2-(2-吡啶)咪唑与金属砌块的螯合作用,我们设计合成了铂金属配合物L2-Pt和L4-Pt。研究结果显示,配合物L2-Pt不仅展示了良好的近红外的光致变色性能,而且还展示了荧光“turn on”的性能。据我们所知,这是第一例荧光“turn on”且近红外光致变色的金属二芳基乙烯分子开关,这种分子开关在高分辨荧光成像和生物荧光标签方面具有潜在的应用价值。
In recent years, molecular electronic devices (such as molecular field effect tube, molecular rectifier, molecular memory, molecular wire, molecular switch and molecular motor, etc.) as the next generation of electronic devices have been rapid development. Among them, the molecular switch as the basic unit of future logic and storage circuit has attracted much attention. Among the various molecular switch systems, diarylethenes, due to their excellent thermal stability and outstanding fatigue resistance, are one of the most promising photochromic compounds for practical applications. Therefore, it is very significant to develop the diarylethenes with novel structures and unique performances. In this thesis, we systematically studied the substituent effects, solvent effects, acid-base effect and metal complexing effect on the fluorescent and photochromic properties of2-(2-pyridyl) imidazole containing diarylethene derivatives (PI-BTEs). The main research contents are as follows:
1. For studying the different substituents on the fluorescent and photochromic performances of2-(2-pyridyl) imidazole containing diarylethene derivatives (PI-BTEs), we designed to synthesize a series of diarylethene compounds L1-L5, and studied the solvent effect of the parent compound L3on the fluorescence and photochromic properties. The results would provide some reference and guidance for us to design novel PI-BTEs compounds according to the requirement in future.
2. Because of the acid-base interaction between the alkaline groups (imidazole and pyridine) and the acid, a series of diarylethene derivatives with imidazoles as the ethene bridges (L2, L3, L6and L7) are prepared to investigate the influence on their absorption spectra, fluorescence spectra and thermal stability by the acid. It has been demonstrated that not only switch of the diarylethene derivatives between P-type and T-type photochromism by the acid stimuli (this photochromic compound has a potential application in rewritable papers of write-by light/erase-by-heat systems) is achieved, but also the reversible acid induced gating "lock" regulation by adjusting the quantity of acid is accomplished. The strong acid plays a gated "lock" role and the alkaline triethylamine may act as the "key" role in this process. Such gating photochromism has potential applications in nondestructive readout.
3. By chelating metallic subunits with2-(2-pyridyl) imidazole, we designed to synthesize the platinum complexes of L2-Pt and L4-Pt. The results show that L2-Pt complex exhibits not only the near-infrared photochromism but also the turn-on fluorescence. To the best of our knowledge, this is the first turn-on fluorescence and near-infrared photochromism of metal diarylethene molecular switch, which has potential applications in the high resolution fluorescence imaging and biological fluorescence label.
引文
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