Journal
CHINESE CHEMICAL LETTERS
Volume 33, Issue 11, Pages 4896-4899Publisher
ELSEVIER SCIENCE INC
DOI: 10.1016/j.cclet.2022.02.076
Keywords
Molecular recognition; Host-guest chemistry; Endo-functionalized cavity; Hydrogen bond; Naphthobox
Categories
Funding
- National Natural Science Foundation of China [22125105]
- Shenzhen Science and Technology Innovation Committee [JCYJ20180504165810828]
- Guangdong Provincial Key Laboratory of Catalysis [2020B121201002]
- Shenzhen Pengcheng Scholar, Guangdong High-Level Personnel of Special Support Program [2019TX05C157]
- Croucher Foundation
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In this study, an endo-functionalized naphthobox was reported to exhibit highly selective binding towards methyl viologen over other analogues. X-ray single crystal structure and Density Functional Theory (DFT) calculations revealed that the endo-functionalized groups in the cavity of the naphthobox played a crucial role in achieving the high binding selectivity through multiple C-H···N, C-H···π, and π···π interactions with methyl viologen.
Highly selective binding of structurally similar substrates is common for biomolecular recognition, but is often challenging to realize in synthetic hosts. Herein, we report highly selective binding of methyl viologen over other analogues by an endo-functionalized naphthobox. X-ray single crystal structure and Density Functional Theory (DFT) calculations revealed that the endo-functionalized groups in the cavity of the naphthobox is important for the high binding selectivity through the formation of multiple C-H center dot center dot center dot N, C-H center dot center dot center dot pi, and pi center dot center dot center dot pi interactions with methyl viologen. (C) 2022 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
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