Macroscalar Helices Co‐Assembled from Chirality‐Transferring Temperature‐Responsive Carbohydrate‐Based Bolaamphiphiles and 1,4‐Benzenediboronic Acid,Angewandte Chemie International Edition

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Macroscalar Helices Co‐Assembled from Chirality‐Transferring Temperature‐Responsive Carbohydrate‐Based Bolaamphiphiles and 1,4‐Benzenediboronic Acid
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2021-01-27 , DOI: 10.1002/anie.202100153
Shuang Wang ₁ , Marcel C Forster ₂ , Kai Xue ₂ , Florian Ehlers ₃ , Bo Pang ₁ , Loren B Andreas ₂ , Philipp Vana ₃ , Kai Zhang ₁

Affiliation

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.

中文翻译：

由手性传递温度响应的基于碳水化合物的Bolaamphiphils和1,4-苯二甲硼酸联合组装的大尺度螺旋。

我们提供了由温度响应性的基于碳水化合物的双亲两性亲子（CHO-Bolas）和1,4-苯二硼酸（BDBA）共同组装的大尺度螺旋的第一个示例。CHO-Bolas包含亲水性葡萄糖或甘露糖部分和疏水性香豆素二聚体。他们显示了水溶液中温度响应的可逆胶束-囊泡转变（MVT）。在碱性溶液中，碳水化合物部分与BDBA的硼酸结合后，右旋螺旋通过温度驱动的d葡萄糖或d的手性转移而形成。从分子水平到超分子水平的甘露糖。这些螺旋是由未反应的BDBA，CHO-Bolas和BDBA之间的硼酸酯（BO键）以及自缩合BDBA的环硼酸酐（BO键）共同组装而成的。在氮气下于300°C加热后，这些螺旋分子显示出极好的形态稳定性。此外，由于BDBA的强自缩合和香豆素二聚体的分解，它们发出了明亮的蓝色发光。

更新日期：2021-01-27

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