Selective recognition of methyl viologen by an endo-functionalized naphthobox

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 st...

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Bibliographic Details
Published in:Chinese chemical letters 2022-11, Vol.33 (11), p.4896-4899
Main Authors: Liu, Weier, Kong, Linghui, Quan, Mao, Yao, Huan, Yang, Liupan, Au-Yeung, Ho Yu, Jiang, Wei
Format: Article
Language:English
Subjects:
Endo-functionalized cavity
Host-guest chemistry
Hydrogen bond
Molecular recognition
Naphthobox
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Summary: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 CH⋅⋅⋅N, CH⋅⋅⋅π, and π⋅⋅⋅π interactions with methyl viologen. An endo-functionalized naphthobox shows highly selective binding of methyl viologen over other similar analogues through the formation of multiple CH⋅⋅⋅N hydrogen bonds, CH⋅⋅⋅π, and π⋅⋅⋅π interactions. [Display omitted]
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2022.02.076