β-环糊精及化学修饰β-环糊精的分子识别作用研究
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摘要
第一章：简要介绍了环糊精,化学修饰环糊精以及它们的应用。综述了具有识别功能的环状分子、分子识别的研究方法及其发展概况,简单叙述了分子识别中的手性识别研究。
第二章：在非除氧的p-环糊精(p-CD)体系中,1,2-二溴甲烷(1,2-DBE)可在室温下诱导萘普生对映体的室温磷光发射。核磁数据证明萘普生分子的萘环部分是从β-CD小口端进入空腔内,羧基部分与p-CD外部的羟基之间形成氢键定位在p-CD腔外。而1,2-DBE则作为一种空间填充剂从大口端处竞争进入β-CD的空腔,从而形成一种稳定的三元混合物。在此基础上,通过荧光法计算了各步的包合常数,进一步证明萘普生对映体和1,2-DBE可以同时进入p-CD的空腔中从而形成三组分包结物。时间分辨磷光光谱法表明萘普生对映异构体都表现出双指数衰减,它们的磷光寿命差异(Δτi/τi)分别为32.9%和34.4%。这表明p-CD/1,2-DBE体系中可以实现萘普生对映体的手性识别。最后,利用分子模拟在分子水平对萘普生对映体的手性识别加以辅证,其结果与实验结果一致。
第三章：本章通过6-胺基-6-脱氧-,3-胺基-3-脱氧和2-胺基-2-脱氧-p-环糊精合成了2-,3-和6-位取代的S-萘普生-p-CD,利用13CNMR、HNMR、高分辨质谱和圆二色谱等手段对该2-,3-和6-位取代的S-萘普生-β-CD进行了表征。在此基础上,对化合物1的荧光和磷光性质进行了初步探讨,并比较研究了S-萘普生与S-萘普生-p-CD在不同介质中的荧光和磷光特性。实验表明S-萘普生能进入p-CD的空腔,从而增强其荧光和磷光发射。
第四章：利用室温磷光光谱研究了S-NPX-CDs 1-3对有机客体小分子的选择性识别作用,有机客体小分子包括二溴甲烷、三溴甲烷、二碘甲烷、碘甲烷、四溴化碳、1,2-二溴乙烷、甲醛、溴代环己烷、甲烷、环己烷、甲酸、甲醇、乙醇、和乙酸。实验表明,二溴甲烷可以显著增强S-NPX-CDs 1的室温磷光信号,但对S-NPX-CDs2和3的诱导并不明显。据此,建立了测定痕量二溴甲烷的室温磷光法,并将其用于煤矿矿坑水中痕量二溴甲烷的检测,检测结果与气相色谱-质谱联用法测得的结果相符,进一步表明S-NPX-CDs 1可以作为选择性检测二溴甲烷的超分子受体。最后,通过核磁共振氢谱、圆二色谱、紫外吸收光谱和能量模拟计算等对S-NPX-CDs 1选择性识别二溴甲烷的机理进行了探讨。
Chapter 1:The concept and application of cyclodextrin, modified cyclodextrin were introduced briefly. Summarized the different research technique of chiral discrimination and narrated the orgin and research development of chiral recognition simply.
Chapter 2:Naproxen enantiomers possess strong room temperature phosphorescence (RTP) in (3-cyclodextrin (P-CD) system with a small amount of 1,2-dibromoethane (1, 2-DBE) under ambient conditions. The effects of pH, concentration ofβ-CD and 1, 2-DBE on the RTP of naproxen enantiomers have been investigated in detail. Time-resolved RTP spectroscopy shows that both naproxen enantiomers exhibit bi-exponential decay pattern with lifetimes ofτ1= 4.79±0.13 andτ2=1.51±0.096 ms for R-naproxen, andτ1= 6.67±0.15 andτ2= 2.13±0.061 ms for S-naproxen. The lifetime differences between these enantiomers areΔτ1=1.88 andΔτ2r=0.62 ms, indicating that chiral discrimination of naproxen enantiomers can be achieved inβ-CD/1,2-DBE system. Naproxen enantiomers can form stable complexes withβ-CD and 1,2-DBE in stoichiometric ratios of 1:1:2 and 1:1:1 (naproxen:β-CD:1,2-DBE) and the association constants are 3.20×103 M-4 and 2.43×103 M-3 for the S- and R-enantiomers respectively. The chiral discrimination of R-naproxen and S-naproxen is realized via their difference in interaction with the chiral cavity ofβ-CD due to their difference in stereochemical structure. Finally, molecular modeling is performed to determine the chiral recognition on a molecular level and the results are in good agreement with the experimental data.
Chapter 3:S-naproxen-modified-β-CD (S-NPX-CDs 1-3) were synthesized by the reactions of (S)-(-)-naproxen with 6-amino-6-deoxy-,3-amino-3-deoxy-, and mono(2-amino-2-deoxy-altro).-β-CDs, respectively. All of them were characterized by HRMS and 1H and 13C NMR spectra. On this basis, the fluorescent and phosphorescent properties of 1 were studied preliminary. The fluorescent and phosphorescent properties of S-naproxen and S-naproxen-modified-β-CD in different medium were also compared, and the results showed that S-naproxen can enter intoβ-CD cavity, so the fluorescence and phosphorescence were enhance.
Chapter 4:Firstly, the fluorescence and phosphorescence characteristics of S-NPX-CDs 1-3 were investigated. Then the molecular recognition of S-NPX-CDs 1-3 to small organic objective molecules were explored by RTP method, and the organic small molecules included dibromomethane, bromoform, isodiiodomethane, iodomethane, Carbon Tetrabromide,1,2-dibromomethane, formaldehyde, bromocyclohexane, methane, cyclohexane, formic acid, methanol, ethanol and acetic acid. Among them, only dibromomethane could significantly enhance the RTP signal of S-NPX-CD1, while it had no effect on S-NPX-CDs 2 and 3. Based on this, a RTP method for the determination trace dibromomethane was establised by S-NPX-CDs 1 as the receptor. Then it was applied to determine the content of dibromomethane in coal mine water and the results was in good agreement with the result of GC-MS method. Therefore, a potential RTP sensor of dibromomethane can be developed by S-NPX-CDs 1 as the receptor. Finally, the mechanism was investigated by 1HNMR, dichroism, UV absorption spectra and energy simulatione.
第二章：在非除氧的p-环糊精(p-CD)体系中,1,2-二溴甲烷(1,2-DBE)可在室温下诱导萘普生对映体的室温磷光发射。核磁数据证明萘普生分子的萘环部分是从β-CD小口端进入空腔内,羧基部分与p-CD外部的羟基之间形成氢键定位在p-CD腔外。而1,2-DBE则作为一种空间填充剂从大口端处竞争进入β-CD的空腔,从而形成一种稳定的三元混合物。在此基础上,通过荧光法计算了各步的包合常数,进一步证明萘普生对映体和1,2-DBE可以同时进入p-CD的空腔中从而形成三组分包结物。时间分辨磷光光谱法表明萘普生对映异构体都表现出双指数衰减,它们的磷光寿命差异(Δτi/τi)分别为32.9%和34.4%。这表明p-CD/1,2-DBE体系中可以实现萘普生对映体的手性识别。最后,利用分子模拟在分子水平对萘普生对映体的手性识别加以辅证,其结果与实验结果一致。
第三章：本章通过6-胺基-6-脱氧-,3-胺基-3-脱氧和2-胺基-2-脱氧-p-环糊精合成了2-,3-和6-位取代的S-萘普生-p-CD,利用13CNMR、HNMR、高分辨质谱和圆二色谱等手段对该2-,3-和6-位取代的S-萘普生-β-CD进行了表征。在此基础上,对化合物1的荧光和磷光性质进行了初步探讨,并比较研究了S-萘普生与S-萘普生-p-CD在不同介质中的荧光和磷光特性。实验表明S-萘普生能进入p-CD的空腔,从而增强其荧光和磷光发射。
第四章：利用室温磷光光谱研究了S-NPX-CDs 1-3对有机客体小分子的选择性识别作用,有机客体小分子包括二溴甲烷、三溴甲烷、二碘甲烷、碘甲烷、四溴化碳、1,2-二溴乙烷、甲醛、溴代环己烷、甲烷、环己烷、甲酸、甲醇、乙醇、和乙酸。实验表明,二溴甲烷可以显著增强S-NPX-CDs 1的室温磷光信号,但对S-NPX-CDs2和3的诱导并不明显。据此,建立了测定痕量二溴甲烷的室温磷光法,并将其用于煤矿矿坑水中痕量二溴甲烷的检测,检测结果与气相色谱-质谱联用法测得的结果相符,进一步表明S-NPX-CDs 1可以作为选择性检测二溴甲烷的超分子受体。最后,通过核磁共振氢谱、圆二色谱、紫外吸收光谱和能量模拟计算等对S-NPX-CDs 1选择性识别二溴甲烷的机理进行了探讨。
Chapter 1:The concept and application of cyclodextrin, modified cyclodextrin were introduced briefly. Summarized the different research technique of chiral discrimination and narrated the orgin and research development of chiral recognition simply.
Chapter 2:Naproxen enantiomers possess strong room temperature phosphorescence (RTP) in (3-cyclodextrin (P-CD) system with a small amount of 1,2-dibromoethane (1, 2-DBE) under ambient conditions. The effects of pH, concentration ofβ-CD and 1, 2-DBE on the RTP of naproxen enantiomers have been investigated in detail. Time-resolved RTP spectroscopy shows that both naproxen enantiomers exhibit bi-exponential decay pattern with lifetimes ofτ1= 4.79±0.13 andτ2=1.51±0.096 ms for R-naproxen, andτ1= 6.67±0.15 andτ2= 2.13±0.061 ms for S-naproxen. The lifetime differences between these enantiomers areΔτ1=1.88 andΔτ2r=0.62 ms, indicating that chiral discrimination of naproxen enantiomers can be achieved inβ-CD/1,2-DBE system. Naproxen enantiomers can form stable complexes withβ-CD and 1,2-DBE in stoichiometric ratios of 1:1:2 and 1:1:1 (naproxen:β-CD:1,2-DBE) and the association constants are 3.20×103 M-4 and 2.43×103 M-3 for the S- and R-enantiomers respectively. The chiral discrimination of R-naproxen and S-naproxen is realized via their difference in interaction with the chiral cavity ofβ-CD due to their difference in stereochemical structure. Finally, molecular modeling is performed to determine the chiral recognition on a molecular level and the results are in good agreement with the experimental data.
Chapter 3:S-naproxen-modified-β-CD (S-NPX-CDs 1-3) were synthesized by the reactions of (S)-(-)-naproxen with 6-amino-6-deoxy-,3-amino-3-deoxy-, and mono(2-amino-2-deoxy-altro).-β-CDs, respectively. All of them were characterized by HRMS and 1H and 13C NMR spectra. On this basis, the fluorescent and phosphorescent properties of 1 were studied preliminary. The fluorescent and phosphorescent properties of S-naproxen and S-naproxen-modified-β-CD in different medium were also compared, and the results showed that S-naproxen can enter intoβ-CD cavity, so the fluorescence and phosphorescence were enhance.
Chapter 4:Firstly, the fluorescence and phosphorescence characteristics of S-NPX-CDs 1-3 were investigated. Then the molecular recognition of S-NPX-CDs 1-3 to small organic objective molecules were explored by RTP method, and the organic small molecules included dibromomethane, bromoform, isodiiodomethane, iodomethane, Carbon Tetrabromide,1,2-dibromomethane, formaldehyde, bromocyclohexane, methane, cyclohexane, formic acid, methanol, ethanol and acetic acid. Among them, only dibromomethane could significantly enhance the RTP signal of S-NPX-CD1, while it had no effect on S-NPX-CDs 2 and 3. Based on this, a RTP method for the determination trace dibromomethane was establised by S-NPX-CDs 1 as the receptor. Then it was applied to determine the content of dibromomethane in coal mine water and the results was in good agreement with the result of GC-MS method. Therefore, a potential RTP sensor of dibromomethane can be developed by S-NPX-CDs 1 as the receptor. Finally, the mechanism was investigated by 1HNMR, dichroism, UV absorption spectra and energy simulatione.
引文
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