Induction of chirality in an achiral monolayer at the liquid/solid interface by a supramolecular chiral auxiliary

I. Cat, de, Zongxia Guo, S.J. George, E.W. Meijer, A.P.H.J. Schenning, S. Feyter, de

Research output: Contribution to journalArticleAcademicpeer-review

60 Citations (Scopus)

Abstract

An achiral oligo(p-phenylene vinylene) derivative with a ureido-triazine hydrogen bonding unit self-assembles into rows of hydrogen bonded dimers at the liquid/solid interface. Scanning tunneling microscopy reveals the formation of chiral domains, but overall, the surface remains racemic. Addition of a chiral auxiliary which is able to interact with the dimers through hydrogen bonding, showed that global organizational chirality could be achieved since a majority of the domains show the same handedness. After removing the chiral auxiliary with a volatile solvent, the global organizational chirality could be trapped, revealing a memory effect. With this straightforward supramolecular approach, we were able to create a chiral surface with preferred handedness composed of achiral molecules at the air/solid interface.
Original languageEnglish
Pages (from-to)3171-3177
JournalJournal of the American Chemical Society
Volume134
Issue number6
DOIs
Publication statusPublished - 2012

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