Sequence-defined oligo(: Ortho -arylene) foldamers derived from the benzannulation of ortho (arylene ethynylene)s

Dan Lehnherr, Chen Chen, Zahra Pedramrazi, Catherine R. Deblase, Joaquin M. Alzola, Ivan Keresztes, Emil B. Lobkovsky, Michael F. Crommie, William R. Dichtel*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

Abstract

A Cu-catalyzed benzannulation reaction transforms ortho(arylene ethynylene) oligomers into ortho-arylenes. This approach circumvents iterative Suzuki cross-coupling reactions previously used to assemble hindered ortho-arylene backbones. These derivatives form helical folded structures in the solid-state and in solution, as demonstrated by X-ray crystallography and solution-state NMR analysis. DFT calculations of misfolded conformations are correlated with variable-temperature 1H and EXSY NMR to reveal that folding is cooperative and more favorable in halide-substituted naphthalenes. Helical ortho-arylene foldamers with specific aromatic sequences organize functional π-electron systems into arrangements ideal for ambipolar charge transport and show preliminary promise for the surface-mediated synthesis of structurally defined graphene nanoribbons.

Original languageEnglish (US)
Pages (from-to)6357-6364
Number of pages8
JournalChemical Science
Volume7
Issue number10
DOIs
StatePublished - 2016

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Sequence-defined oligo(: Ortho -arylene) foldamers derived from the benzannulation of ortho (arylene ethynylene)s'. Together they form a unique fingerprint.

Cite this