Macroscalar Helices Co‐Assembled from Chirality‐Transferring Temperature‐Responsive Carbohydrate‐Based Bolaamphiphiles and 1,4‐Benzenediboronic Acid
| Autor: | Philipp Vana, Kai Xue, Florian Ehlers, Loren B. Andreas, Shuang Wang, Kai Zhang, Marcel C. Forster, Bo Pang |
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| Rok vydání: | 2021 |
| Předmět: |
assembly
Aqueous solution chirality transfer 010405 organic chemistry Dimer Supramolecular chemistry Bolaamphiphile Mannose General Chemistry 010402 general chemistry 01 natural sciences Boroxine Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Polymer chemistry temperature-responsive Helices | Hot Paper helices Chirality (chemistry) Luminescence bolaamphiphile Research Articles Research Article |
| Zdroj: | Angewandte Chemie (International Ed. in English) |
| ISSN: | 1521-3773 1433-7851 |
| Popis: | We present the first example of macroscalar helices co‐assembled from temperature‐responsive carbohydrate‐based bolaamphiphiles (CHO‐Bolas) and 1,4‐benzenediboronic acid (BDBA). The CHO‐Bolas contained hydrophilic glucose or mannose moieties and a hydrophobic coumarin dimer. They showed temperature‐responsive reversible micelle‐to‐vesicle transition (MVT) in aqueous solutions. After the binding of carbohydrate moieties with boronic acids of BDBA in their alkaline solutions, right‐handed helices were formed via the temperature‐driven chirality transfer of d‐glucose or d‐mannose from the molecular to supramolecular level. These helices were co‐assembled by unreacted BDBA, boronate esters (B−O−C bonds) between CHO‐Bolas and BDBA, as well as boroxine anhydrides (B−O−B bonds) of self‐condensed BDBA. After heating at 300 °C under nitrogen, the helices displayed excellent morphological stability. Moreover, they emitted bright blue luminescence caused by strong self‐condensation of BDBA and decomposition of coumarin dimers. Macroscalar, thermally stable helices were formed by co‐assembly of temperature‐responsive carbohydrate‐based bolaamphiphiles and 1,4‐benzenediboronic acids accompanying chirality transfer in alkaline solutions during the temperature decrease from 80 °C to room temperature. |
| Databáze: | OpenAIRE |
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