富勒烯作为模板剂的碗烯基分子笼构筑的自组装

doi:10.6023/cjoc201904042

有机化学 ›› 2019, Vol. 39 ›› Issue (10): 2867-2874.DOI: 10.6023/cjoc201904042 上一篇下一篇

所属专题：有机超分子化学合辑

研究论文

富勒烯作为模板剂的碗烯基分子笼构筑的自组装

孙卫东, 叶琳, 刘佳, 郑璐, 郭文彩, 韩森凯, 邵成园, 江华^*()

北京师范大学化学学院理论与计算光化学教育部重点实验室北京 100875

收稿日期:2019-04-16 修回日期:2019-05-08 发布日期:2019-06-03
通讯作者: 江华 E-mail:jiangh@bnu.edu.cn
基金资助:
国家重点基础研究发展计划(973 Program);国家重点基础研究发展计划(2015CB856502);国家重点基础研究发展计划(973计划);国家重点基础研究发展计划(No. 2015CB856502);国家自然科学基金(Nos. 21572023);国家自然科学基金(21672026)

Self-Assembled of Corannulene-Based Molecular Cage with Fullerenes as Template

Sun, Weidong, Ye, Lin, Liu, Jia, Zheng, Lu, Guo, Wencai, Han, Senkai, Shao, Chengyuan, Jiang, Hua^*()

Key Laboratory of Theoretical and Computational Photochemistry and Key Laboratory of Radiopharmaceuticals,College of Chemistry, Beijing Normal University, Beijing 100875

Received:2019-04-16 Revised:2019-05-08 Published:2019-06-03
Contact: Jiang, Hua E-mail:jiangh@bnu.edu.cn
Supported by:
Project supported by the Major State Basic Research Development Program of China(973 Program);Project supported by the Major State Basic Research Development Program of China(2015CB856502);Project supported by the Major State Basic Research Development Program of China(973计划);Project supported by the Major State Basic Research Development Program of China(No. 2015CB856502);the National Natural Science Foundation of China(Nos. 21572023);the National Natural Science Foundation of China(21672026)

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摘要/Abstract

设计合成了四吡啶基取代的碗烯衍生物COPY2. 通过核磁研究表明, 在模板分子C₆₀或C₇₀存在下, 配体COPY2与金属钯分别在室温和55 ℃下通过自组装形成1∶1分子笼络合物C_60/70?COPY2-Pd. 当络合物C₆₀?COPY2-Pd与C₇₀等物质的量混合或者络合物C₇₀?COPY2-Pd与C₆₀等物质的量混合于90 ℃加热48 h后, 络合物C₆₀?COPY2-Pd与C₇₀?COPY2-Pd的比例均为4∶1. 将配体COPY2与Pd(CH₃CN)₂Cl₂加入等物质的量C₆₀和C₇₀混合物中加热平衡后, 络合物C₆₀?COPY2-Pd与C₇₀?COPY2-Pd的比例同样为4∶1. 当C₆₀和C₇₀的比例为2∶1时, 体系中只生成络合物C₆₀?COPY2-Pd; 而当C₆₀和C₇₀的比例为1∶2时, 平衡后络合物C₆₀?COPY2-Pd与C₇₀?COPY2-Pd的比例为3.3∶1. 这些结果表明, 配体COPY2在金属钯存在时对C₆₀络合能力强于C₇₀的络合能力. 加入DMAP能够实现络合物解离, 释放笼内富勒烯并回收COPY2. 因此, 配体COPY2可应用于室温下对C₆₀的富集.

关键词: 碗烯, 分子笼, 富勒烯, 自组装

A tetrapyridyl substituted corannulene derivative COPY2 was designed and synthesized. Only in the presence of template molecule C₆₀ or C₇₀, COPY2 and palladium could form 1∶1 molecular cage complex C_60/70?COPY2-Pd by self-assembly at room temperature and 55 ℃ respectively. C₆₀ and C₇₀ were used not only as a template for constructing target molecular cages, but also as a stabilizer for molecular cage. When 1.0 equiv. C₇₀ mixed with C₆₀?COPY2-Pd or 1.0 equiv. C₆₀ mixed with C₇₀?COPY2-Pd, the ratio of complex C₆₀?COPY2-Pd to C₇₀?COPY2-Pd is 4∶1 after the mixtures were heated at 90 ℃ for 48 h, which is consistent with the ratio of COPY2 and Pd(CH₃CN)₂Cl₂ mixed with C₆₀ and C₇₀ (1∶1). Only the complex C₆₀?COPY2-Pd was observed when the ratio of C₆₀ to C₇₀ is 2∶1. However, even the ratio of C₆₀ to C₇₀ is 1∶2, complex C₆₀?COPY2-Pd is still the dominant species in the mixture. These results demonstrate that complexing ability of COPY2 with C₆₀ is stronger than that of COPY2 with C₇₀. 4-Dimethylaminopyridine (DMAP) was chosen to dissociate the cage so as to release fullerene and ligand. Therefore, the ligand COPY2 could be used to the enrichment of C₆₀ at room temperature.

Key words: corannulene, molecular cage, fullerene, self-assembly

引用此文

孙卫东, 叶琳, 刘佳, 郑璐, 郭文彩, 韩森凯, 邵成园, 江华. 富勒烯作为模板剂的碗烯基分子笼构筑的自组装[J]. 有机化学, 2019, 39(10): 2867-2874.

Sun, Weidong, Ye, Lin, Liu, Jia, Zheng, Lu, Guo, Wencai, Han, Senkai, Shao, Chengyuan, Jiang, Hua. Self-Assembled of Corannulene-Based Molecular Cage with Fullerenes as Template[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2867-2874.

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图/表 7

图1. 碗烯衍生物COPY、COPY1和COPY2的结构

Figure 1. Corannulene derivatives of COPY, COPY1 and COPY2

图2. 配体COPY2与金属钯的自组装示意图

Figure 2. Self-assemble of COPY2 with Pd(CH3CN)2Cl2

图3. (a)络合物C70?COPY2-Pd、(b) C60?COPY2-Pd和(c)配体COPY2的部分核磁谱图(600 MHz, 298 K, TCE-d2)

Figure 3. Part 1H NMR (600 MHz, 298 K, TCE-d2) spectra of (a) C70?COPY2-Pd, (b) C60?COPY2-Pd and (c) COPY2

图4. (a)络合物C60?COPY2-Pd、(b)分子笼、络合物C60?COPY1-Pd, 以及络合物C60?COPY2-Pd (250 μL, 0.5 mmol?L–1)与分子笼COPY1-Pd (250 μL, 0.5 mmol?L–1)混合后加热至90 ℃ (c) 5、(d) 9、(e) 24 h和130 ℃ (f) 5、(g) 16 h、(h) 3 d后的部分核磁谱图(600 MHz, 298 K, TCE-d2)

Figure 4. Part 1H NMR (600 MHz, TCE-d6, 298 K) spectra of (a) C60?COPY2-Pd, (b) COPY1-Pd, a mixture of C60? COPY2-Pd (250 μL, 0.5 mmol?L–1) and COPY1-Pd (250 μL, 0.5 mmol?L–1) was heated at 90 ℃ for (c) 6, (d) 9 and (e) 24 h, heated at 130 ℃ for (f) 5 h, (g) 16 h and (h) 3 d

图5. 络合物C60?COPY2-Pd (a)以及络合物C60?COPY2-Pd (0.5 mmol?L–1, 0.5 mL TCE-d2)加入1.0 equiv. C70分别在90 ℃下加热(b) 12、(c) 24和(d) 48 h的部分核磁图(600 MHz, 298 K)

Figure 5. Part 1H NMR (600 MHz, TCE-d2, 298 K) spectra of (a) C60?COPY2-Pd, and C60?COPY2-Pd (0.5 mmol?L–1, 0.5 mL TCE-d2) added C70 (1 equiv.) and heated at 90 ℃ for (b) 12 (c) 24 and (d) 48 h

图6. 络合物C60/70?COPY2-Pd的富勒烯置换示意图

Figure 6. Illustration of fullerene displacement for C60/70?COPY2-Pd

图7. 配体COPY2 (1.0 mmol?L–1, 0.5 mL, 1 equiv.)与Pd(CH3- CN)2Cl2 (2 equiv.)和C60/C70 (1 equiv./1 equiv.)混合后分别在90 ℃加热(a) 12, (b) 24和(c) 48 h; 110 ℃加热(d) 12, (e) 24和(f) 48 h; 130 ℃加热(g) 12, (h) 24, (i) 36和(j) 48 h以及(k)络合物C60?COPY2-Pd, (l)络合物C70?COPY2-Pd的部分核磁谱图(600 MHz, 298 K, TCE-d2)

Figure 7. Part 1H NMR (600 MHz, TCE-d2, 298 K) spectra of a mixture of COPY2 (1.0 mmol?L–1, 0.5 mL, 1 equiv.) and Pd(CH3CN)2Cl2 (2 equiv.) added C60/C70 (1 equiv./1 equiv.) and heated at 90 ℃ for (a) 12, (b) 24 and (c) 48 h, 110 ℃ for (d) 12, (e) 24 and (f) 48 h, 130 ℃ for (g) 12, (h) 24, (i) 36 and (j) 48 h, (k) C60?COPY2-Pd, (l) C70?COPY2-Pd

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富勒烯作为模板剂的碗烯基分子笼构筑的自组装

Self-Assembled of Corannulene-Based Molecular Cage with Fullerenes as Template

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