PCage: Fluorescent Molecular Temples for Binding Sugars in Water
| العنوان: | PCage: Fluorescent Molecular Temples for Binding Sugars in Water |
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| المؤلفون: | George C. Schatz, Yu Tan, J. Fraser Stoddart, Xiao-Yang Chen, Yunyan Qiu, Long Zhang, Bo Song, Yuanning Feng, Leighton O. Jones, Wenqi Liu, Qing-Hui Guo |
| المصدر: | Journal of the American Chemical Society. 143:15688-15700 |
| بيانات النشر: | American Chemical Society (ACS), 2021. |
| سنة النشر: | 2021 |
| مصطلحات موضوعية: | Aqueous solution, Hydrogen bond, General Chemistry, Carbohydrate, Biochemistry, Fluorescence, Combinatorial chemistry, Catalysis, chemistry.chemical_compound, Colloid and Surface Chemistry, chemistry, Synthetic Receptors, Pyrene, Pyridinium, Receptor |
| الوصف: | 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-shaped 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 glycopyranosyl rings in the carbohydrate-based substrates. In addition, eight 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 is useful for glucose-sensing in aqueous solution. |
| تدمد: | 1520-5126 0002-7863 |
| DOI: | 10.1021/jacs.1c06333 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::8e3bf4e3e85834cba0130b8a1af1723e https://doi.org/10.1021/jacs.1c06333 |
| Rights: | CLOSED |
| رقم الانضمام: | edsair.doi.dedup.....8e3bf4e3e85834cba0130b8a1af1723e |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 15205126 00027863 |
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| DOI: | 10.1021/jacs.1c06333 |