Reversing the Handedness of Self-Assembled Porous Molecular Networks through the Number of Identical Chiral Centres

Kazukuni Tahara*, Aya Noguchi, Ruri Nakayama, Elke Ghijsens, Steven De Feyter, Yoshito Tobe

*Corresponding author for this work

Research output: Contribution to journalArticle

5 Scopus citations

Abstract

Scanning tunnelling microscope observations at the 1-phenyloctane/graphite interface reveal how chiral structural information at the molecular level is transferred and expressed structurally at the 2D supramolecular level for a porous system. The chirality of self-assembled molecular networks formed by chiral dehydrobenzo[12]annulene (cDBA) derivatives having three chiral chains and three achiral chains, alternatingly, is compared with those of cDBAs having six chiral chains reported previously. While for all cDBAs homochiral surfaces are formed, their handedness is not simply a reflection of the absolute configuration of the stereogenic centres. Both the number of stereogenic centres as well as the length of the achiral chains determine the supramolecular handedness, providing a deep insight into the supramolecular chirality induction mechanisms at play. Moreover, these cDBAs act to induce chirality in porous networks formed by achiral DBAs.

Original languageEnglish
Pages (from-to)7733-7738
Number of pages6
JournalAngewandte Chemie - International Edition
Volume58
Issue number23
DOIs
StatePublished - 3 Jun 2019

Keywords

  • chirality
  • dehydrobenzo[12]annulene
  • liquid/solid interfaces
  • scanning tunnelling microscopy
  • self-assembly

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