Bisindeno-annulated pentacenes with exceptionally high photo-stability and ordered molecular packing: Simple synthesis by a regio-selective Scholl reaction

Arun Naibi Lakshminarayana, Jingjing Chang, Jie Luo, Bin Zheng, Kuo-Wei Huang, Chunyan Chi

Research output: Contribution to journalArticlepeer-review

45 Scopus citations

Abstract

Bisindeno-annulated pentacenes 3a and 3b were synthesized by a simple regio-selective, FeCl3-mediated Scholl reaction from the corresponding 6,13-diaryl pentacene precursors. The fusion of two indeno-units dramatically changes the electronic properties and chemical reactivity of pentacene and the obtained compounds exhibited exceptionally high photo-stability in the solution, with a half-life time of 11.2 (3a) and 32.0 (3b) days under ambient light and air conditions. Ordered molecular packing with a small π-π stacking distance was observed in the single crystals of 3a and 3b. Our research provides a promising strategy to access stable higher order acenes with controlled molecular order. This journal is
Original languageEnglish (US)
Pages (from-to)3604-3607
Number of pages4
JournalChem. Commun.
Volume51
Issue number17
DOIs
StatePublished - 2015

ASJC Scopus subject areas

  • Materials Chemistry
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Ceramics and Composites
  • Chemistry(all)
  • Catalysis
  • Electronic, Optical and Magnetic Materials

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