Hexabenzocoronene Graphitic Nanocoils Appended with Crown Ethers: Supramolecular Chirality Induced by Host–Guest Interaction |
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| Authors: | Wang Zeng Wei Zhang Xianying Li Wusong Jin Dengqing Zhang |
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| Institution: | 1. College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai, 201620 P. R. China;2. South China Advanced Institute for Soft Matter Science and Technology, South China University of Technology, Guangzhou, 510641 P. R. China;3. College of Environmental Science and Engineering, Donghua University, Shanghai, 201620 P. R. China |
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| Abstract: | We have designed and synthesized two new achiral hexa-peri-hexabenzocoronene (HBC) derivatives, HBCCE and HBCTEG-CE , which bear the crown ether as the pendant for the amino acid binding site. The HBCCE self-assembled into a racemic mixture of P- and M-handed helical nanocoils, however, in the presence of chiral amino acid guests, it formed helical nanocoils with one-handed screw sense. The effects of the concentration, type and configuration of the guests on the induced circular dichroism (ICD) during the co-assembly of HBCCE with chiral amino acids were also investigated. Additionally, after complete removal of the chiral guests, the optically active nanocoils did not racemize, even in the presence of excess amino acids with the opposite configuration. In contrast, HBCTEG-CE with a long triethylene glycol (TEG) chain between the crown ether group and the HBC unit did not exhibit ICD during the co-assembly with chiral amino acids. |
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| Keywords: | crown ether hexa-peri-hexabenzocoronene host–guest interactions induced helical chirality nanocoils |
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