Hierarchical superstructures with control of helicity from the self-assembly of chiral bent-core molecules

Shih Chieh Lin, Rong Ming Ho*, Chin Yen Chang, Chain-Shu Hsu

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

32 Scopus citations

Abstract

Herein, two asymmetric chiral bent-core molecules, 3-[(4-{[4-(heptyloxy) benzoyl]oxy}benzoyl)oxy]-phenyl-4-[(4-{[(1R)-1-methylheptyl]oxy}benzoyl)oxy] benzoate (BC7R) and 3-[(4-{[4-(heptyloxy)benzoyl]oxy}benzoyl)oxy]-phenyl-4-[(4- {[(1S)-1-methylheptyl]oxy}benzoyl)oxy] benzoate (BC7S), were synthesized to demonstrate control of the helicity of their self-assembled hierarchical superstructures. Mirror-imaged CD spectra showed a split-type Cotton effect after the formation of self-assembled aggregates of BC7R and BC7S, thereby suggesting the formation of intermolecular exciton couplets with opposite optical activities. Both twisted and helical ribbons with preferential helicity that corresponded to the twisting character of the intermolecular exciton couplet were found in the aggregates. The formation of helical ribbons was attributed to the merging of twisted ribbons through an increase in width to improve morphological stability. As a result, control of the helicity of hierarchical superstructures from the self-assembly of bent-core molecules could be achieved by taking advantage of the transfer of chiral information from the molecular level onto the hierarchical scale.

Original languageEnglish
Pages (from-to)9091-9098
Number of pages8
JournalChemistry - A European Journal
Volume18
Issue number29
DOIs
StatePublished - 16 Jul 2012

Keywords

  • aggregation
  • bent-core molecules
  • chirality
  • helical structures
  • self-assembly

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