Decreasing aromaticity in π-conjugated materials: Efficient synthesis and electronic structure identification of cyclopentadiene-containing systems

Lei Chen, Sufian M. Mahmoud, Xiaodong Yin, Roger A. Lalancette, Agostino Pietrangelo

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

An efficient route to cyclopentadiene-containing π-conjugated molecules is reported. A comparative analysis between the aryl/dienyl hybrids and their aromatic congeners shows a propensity of the diene moiety to reduce the optical band gap of a π-conjugated system without compromising a planar structural topology. Moreover, a novel poly(fluorene) derivative bearing alternating cyclopentadiene repeat units was synthesized to demonstrate the applicability of this method in polymer synthesis.

Original languageEnglish (US)
Pages (from-to)5970-5973
Number of pages4
JournalOrganic letters
Volume15
Issue number23
DOIs
StatePublished - Dec 6 2013

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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