Backbone-Rigidified Oligo(m-phenylene ethynylenes)

Xiaowu Yang, Lihua Yuan, Kazuhiro Yamato, Amy L. Brown, Wen Feng, Mako Furukawa, Xiao Cheng Zeng, Bing Gong

Research output: Contribution to journalArticle

80 Citations (Scopus)

Abstract

Oligo(m-phenylene ethynylenes) (oligo(m-PE)) with backbones rigidified by intramolecular hydrogen bonds were found to fold into well-defined conformations. The localized intramolecular hydrogen bond involves a donor and an acceptor from two adjacent benzene rings, respectively, which enforces globally folded conformations on these oligomers. Oligomers with two to seven residues have been synthesized and characterized. The persistence of the intramolecular hydrogen bonds and the corresponding curved conformations were established by ab initio and molecular mechanics calculations, 1D and 2D 1H NMR spectroscopy, and UV spectroscopy. Pentamer 5, hexamer 6, and heptamer 7 adopt well-defined helical conformations. Such a backbone-based conformational programming should lead to molecules whose conformations are resilient toward structural variation of the side groups. These m-PE oligomers have provided a new approach for achieving folded unnatural oligomers under conditions that are otherwise unfavorable for previously described, solvent-driven folding of m-PE foldamers. Stably folded structures based on the design principle described here can be developed and may find important applications.

Original languageEnglish (US)
Pages (from-to)3148-3162
Number of pages15
JournalJournal of the American Chemical Society
Volume126
Issue number10
DOIs
StatePublished - Mar 17 2004

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Conformations
Hydrogen
Oligomers
Hydrogen bonds
Benzene
Mechanics
Spectrum Analysis
Magnetic Resonance Spectroscopy
Molecular mechanics
Ultraviolet spectroscopy
Nuclear magnetic resonance spectroscopy
Molecules
Proton Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Yang, X., Yuan, L., Yamato, K., Brown, A. L., Feng, W., Furukawa, M., ... Gong, B. (2004). Backbone-Rigidified Oligo(m-phenylene ethynylenes). Journal of the American Chemical Society, 126(10), 3148-3162. https://doi.org/10.1021/ja039416d

Backbone-Rigidified Oligo(m-phenylene ethynylenes). / Yang, Xiaowu; Yuan, Lihua; Yamato, Kazuhiro; Brown, Amy L.; Feng, Wen; Furukawa, Mako; Zeng, Xiao Cheng; Gong, Bing.

In: Journal of the American Chemical Society, Vol. 126, No. 10, 17.03.2004, p. 3148-3162.

Research output: Contribution to journalArticle

Yang, X, Yuan, L, Yamato, K, Brown, AL, Feng, W, Furukawa, M, Zeng, XC & Gong, B 2004, 'Backbone-Rigidified Oligo(m-phenylene ethynylenes)', Journal of the American Chemical Society, vol. 126, no. 10, pp. 3148-3162. https://doi.org/10.1021/ja039416d
Yang X, Yuan L, Yamato K, Brown AL, Feng W, Furukawa M et al. Backbone-Rigidified Oligo(m-phenylene ethynylenes). Journal of the American Chemical Society. 2004 Mar 17;126(10):3148-3162. https://doi.org/10.1021/ja039416d
Yang, Xiaowu ; Yuan, Lihua ; Yamato, Kazuhiro ; Brown, Amy L. ; Feng, Wen ; Furukawa, Mako ; Zeng, Xiao Cheng ; Gong, Bing. / Backbone-Rigidified Oligo(m-phenylene ethynylenes). In: Journal of the American Chemical Society. 2004 ; Vol. 126, No. 10. pp. 3148-3162.
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