Synthesis, Aromaticity, and Application of peri-Pentacenopentacene: Localized Representation of Benzenoid Aromatic Compounds

Tanguy Jousselin-Oba, Masashi Mamada, Karen Wright, Jérome Marrot, Chihaya Adachi, Abderrahim Yassar, Michel Frigoli

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

We report the synthesis and optoelectronic properties of TIPS-peri-pentacenopentacene (TIPS-PPP), a vertical extension of TIPS-pentacene (TIPS-PEN) and a low-band-gap material with remarkable stability. We found the synthetic conditions to avoid the competition between 1,2- and 1,4-addition of lithium acetylide on the large aromatic dione. The high stability of TIPS-PPP is due to the peri-fusion which increases the aromaticity by generating two localized aromatic sextets that are flanked with 2 diene fragments, similar to two fused-anthracenes. Like TIPS-PEN, TIPS-PPP shows the archetypal 2D brickwall motif in crystals with a larger transfer integral and smaller reorganization energy. The high mobility of up to 1 cm2 V−1 s−1 was obtained in an organic field-effect transistor fabricated by a wet process. Also, TIPS-PPP was used as a near-infrared (NIR) emitter for NIR organic-light-emitting-diode devices resulting in a high external quantum efficiency at 800 nm.

Original languageEnglish
Article numbere202112794
JournalAngewandte Chemie - International Edition
Volume61
Issue number1
DOIs
Publication statusPublished - Jan 3 2022

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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