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Binding Sugars in Water Inside Molecular Temples

92 Pages Posted: 23 Apr 2021 Publication Status: Review Complete

See all articles by Wenqi Liu

Wenqi Liu

Northwestern University - Department of Chemistry

Yu Tan

Sun Yat-Sen University (SYSU) - School of Chemical Engineering and Technology

Bo Song

Northwestern University - Department of Chemistry

Qing-Hui Guo

Northwestern University - Department of Chemistry

Long Zhang

Northwestern University - Department of Chemistry

Yunyan Qiu

Northwestern University

Yuanning Feng

Northwestern University

Xiao-Yang Chen

Northwestern University - Department of Chemistry

J. Fraser Stoddart

Northwestern University - Department of Chemistry

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Abstract

The development of synthetic receptors that recognize carbohydrates in water with high selectivity and specificity is challenging on account of their structural complexity and strong hydrophilicity. Here, we report on the design and synthesis of two pyrene-based, temple receptors for the recognition of a range of common sugars in water. These receptors rely on the use of two parallel pyrene panels, which serve as roofs and floors, capable of forming multiple [C–H•••π] interactions with the axially oriented C–H bonds on glycolpyranosyl rings in the carbohydrate-based substrates. In addition, 8 polarized pyridinium C–H bonds, projecting from the roofs and floors of the temple receptors toward the binding cavities, form [C–H•••O] hydrogen bonds with the equatorially oriented OH groups on the sugars located inside the hydrophobic cavities. Four  para -xylylene pillars play a crucial role in controlling the distance between the roof and floor. These temple receptors are highly selective for the binding of glucose and its derivatives. Furthermore, they show enhanced fluorescence upon binding with glucose in water, a property which could be integrated into glucose-sensing devices.

Keywords: Carbohydrates, Cyclophanes, [C–H•••π] Interactions, Fluorescence, Hydrogen Bonding, Molecular Cages, Molecular Modeling, Sensing.

Suggested Citation

Liu, Wenqi and Tan, Yu and Song, Bo and Guo, Qing-Hui and Zhang, Long and Qiu, Yunyan and Feng, Yuanning and Chen, Xiao-Yang and Stoddart, J. Fraser, Binding Sugars in Water Inside Molecular Temples. Available at SSRN: https://ssrn.com/abstract=3832980 or http://dx.doi.org/10.2139/ssrn.3832980
This version of the paper has not been formally peer reviewed.

Wenqi Liu

Northwestern University - Department of Chemistry

Evanston, IL
United States

Yu Tan

Sun Yat-Sen University (SYSU) - School of Chemical Engineering and Technology ( email )

Zhuhai
China

Bo Song

Northwestern University - Department of Chemistry

Evanston, IL
United States

Qing-Hui Guo

Northwestern University - Department of Chemistry ( email )

Evanston, IL
United States

Long Zhang

Northwestern University - Department of Chemistry

Evanston, IL
United States

Yunyan Qiu

Northwestern University

2001 Sheridan Road
Evanston, IL 60208
United States

Yuanning Feng

Northwestern University

2001 Sheridan Road
Evanston, IL 60208
United States

Xiao-Yang Chen

Northwestern University - Department of Chemistry ( email )

Evanston, IL
United States

J. Fraser Stoddart (Contact Author)

Northwestern University - Department of Chemistry ( email )

Evanston, IL
United States

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