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Macroscalar Helices Co‐Assembled from Chirality‐Transferring Temperature‐Responsive Carbohydrate‐Based Bolaamphiphiles and 1,4‐Benzenediboronic Acid
Author(s) -
Wang Shuang,
Forster Marcel C.,
Xue Kai,
Ehlers Florian,
Pang Bo,
Andreas Loren B.,
Vana Philipp,
Zhang Kai
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202100153
Subject(s) - chemistry , dimer , supramolecular chemistry , chirality (physics) , aqueous solution , mannose , boronic acid , stereochemistry , crystallography , organic chemistry , crystal structure , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
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.