Determining Chiral Configuration of Diamines via Contact Angle Measurements on Enantioselective Alanine-Appended Benzene-Tricarboxamide Gelators

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• 作者：Sung Ho Jung ; Ka Young Kim ; Ahreum Ahn ; Myong Yong Choi ; Justyn Jaworski ; Jong Hwa Jung
• 刊名：ACS Applied Materials & Interfaces
• 出版年：2016
• 出版时间：June 8, 2016
• 年：2016
• 卷：8
• 期：22
• 页码：14102-14108
• 全文大小：393K
• 年卷期：0
• ISSN：1944-8252

文摘

Spectroscopic techniques exist that may discern between enantiomers and assess chiral purity. A nonspectroscopic approach that may be directly observed could provide numerous benefits. Using chiral alanine-appended benzene-tricarboxamide gelators, we reveal a methanol gel system that is capable of providing visual discrimination between enantiomers of various diamines. Specifically, gelation is induced by supramolecular nanofiber assembly resulting from interaction between a chiral gelator and a diamine of opposing chirality (i.e., a heterochiral system). Upon further implementing the chiral gelator in electrospun fibers as solid state films, we revealed enantioselective surface wetting properties that allowed for determining chirality through contact angle measurements. While these two approaches of observable gelation and surface wetting offer nonspectroscopic approaches, we also find that the supramolecular nanofiber assembly was able to enhance the induced circular dichroism signal resulting from addition of chiral diamines, allowing precise quantification of their enantiomeric purity.