Regioselective Transformation of Long π-Conjugated Backbones: From Oligofurans to Oligoarenes

Sunita Gadakh, Linda J.W. Shimon, Ori Gidron*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

We demonstrate the transformation of oligofurans through sequential Diels–Alder cycloaddition reactions to provide oligoarenes in two chemical steps, regardless of the oligomer length. By this method, oligonaphthalenes containing up to six units were obtained in high yield through the formation of up to 12 new C−C bonds. The versatility of this method was demonstrated for various polyaromatic hydrocarbons. The regioselectivity of this process enabled the synthesis of a library of substituted triarylenes from a single terfuran precursor by modification of the dienophile strength and the order of addition. Overall, this study demonstrates that long oligofurans are interesting not only as organic electronic materials, but also as starting materials for the formation of various conjugated systems.

Original languageAmerican English
Pages (from-to)13601-13605
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number44
DOIs
StatePublished - 23 Oct 2017

Bibliographical note

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • Diels–Alder cycloaddition
  • oligoarenes
  • oligofurans
  • organic electronic materials
  • π conjugation

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