Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 1, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202112794
Keywords
acenoacenes; aromaticity; Clar's representation; organic light-emitting diodes; structure elucidation
Categories
Funding
- Agence Nationale de la Recherche [ANR-16-CE07-0024]
- JST ERATO [JPMJER1305]
- JSPS KAKENHI [19H02790, 21H05401]
- JSPS Core-to-Core Program [JPJSCCA20180005]
- Inamori Foundation
- Iketani Science and Technology Foundation
- Grants-in-Aid for Scientific Research [21H05401] Funding Source: KAKEN
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The synthesis and optoelectronic properties of TIPS-peri-pentacenopentacene (TIPS-PPP) were reported, showing high stability and mobility for use in organic field-effect transistors and near-infrared organic light-emitting diodes. The unique structure of TIPS-PPP with a 2D brickwall motif in crystals leads to enhanced performance in devices.
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 cm(2) 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.
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