Chinese Journal of Organic Chemistry >
Self-Assembled of Corannulene-Based Molecular Cage with Fullerenes as Template
Received date: 2019-04-16
Revised date: 2019-05-08
Online published: 2019-06-03
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)
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 C60/70?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
Weidong Sun, , Lin Ye, , Jia Liu, , Lu Zheng, , Wencai Guo, , Senkai Han, , Chengyuan Shao, , Hua Jiang, . Self-Assembled of Corannulene-Based Molecular Cage with Fullerenes as Template[J]. Chinese Journal of Organic Chemistry, 2019 , 39(10) : 2867 -2874 . DOI: 10.6023/cjoc201904042
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