Excellent Semiconductors Based on Tetracenotetracene and Pentacenopentacene: From Stable Closed-Shell to Singlet Open-Shell

Tanguy Jousselin-Oba, Masashi Mamada, Jérôme Marrot, Antoine Maignan, Chihaya Adachi, Abderrahim Yassar, Michel Frigoli

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Designing stable open-shell organic materials through the modifications of the π-topology of molecular organic semiconductors has recently attracted considerable attention. However, their uses as an active layer in organic field-effect transistors (OFETs) are very limited, and the obtained hole and electron charge mobilities are around 10-3 cm2 V-1 s-1. Herein, we disclose the synthesis of two peri-fused materials, so-called tetracenotetracene (TT) and pentacenopentacene (PP), which have low band gaps of 1.79 and 1.42 eV, respectively. Their ground state natures have been investigated by different experiments including steady state absorption, electron spin resonance, superconducting quantum interfering device, and variable-temperature NMR along with DFT calculations. TT and PP have closed-shell and singlet open-shell structures in their ground state, respectively, and possess high stability. Their biradical characteristics were found to be 0.50 and 0.64. The origin of the open-shell character of PP is related to the concomitant opening of two tetracenes with the recovering of two extra aromatic sextets and a small HOMO-LUMO energy gap (gap <1.5 eV). Thanks to the high stability, thin film OFET devices could be fabricated. In TG-BC configuration PP shows a remarkably high hole mobility of 1.4 cm2 V-1 s-1, while TT exhibits a hole mobility of 0.77 cm2 V-1 s-1. In the configuration of BG-TC, ambipolar behaviors for both were obtained with hole and electron mobilities of 0.21 and 0.01 cm2 V-1 s-1 for PP and 0.14 and 0.006 cm2 V-1 s-1 for TT.

Original languageEnglish
Pages (from-to)9373-9381
Number of pages9
JournalJournal of the American Chemical Society
Volume141
Issue number23
DOIs
Publication statusPublished - Jun 12 2019

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Semiconductors
Hole mobility
Naphthacenes
Organic field effect transistors
Electrons
Semiconductor materials
Equipment and Supplies
Ground state
Electron Spin Resonance Spectroscopy
Energy gap
Semiconducting organic compounds
Electron mobility
Discrete Fourier transforms
Temperature
Paramagnetic resonance
Nuclear magnetic resonance
Topology
Thin films
Experiments

All Science Journal Classification (ASJC) codes

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

Cite this

Excellent Semiconductors Based on Tetracenotetracene and Pentacenopentacene : From Stable Closed-Shell to Singlet Open-Shell. / Jousselin-Oba, Tanguy; Mamada, Masashi; Marrot, Jérôme; Maignan, Antoine; Adachi, Chihaya; Yassar, Abderrahim; Frigoli, Michel.

In: Journal of the American Chemical Society, Vol. 141, No. 23, 12.06.2019, p. 9373-9381.

Research output: Contribution to journalArticle

Jousselin-Oba, Tanguy ; Mamada, Masashi ; Marrot, Jérôme ; Maignan, Antoine ; Adachi, Chihaya ; Yassar, Abderrahim ; Frigoli, Michel. / Excellent Semiconductors Based on Tetracenotetracene and Pentacenopentacene : From Stable Closed-Shell to Singlet Open-Shell. In: Journal of the American Chemical Society. 2019 ; Vol. 141, No. 23. pp. 9373-9381.
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