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

Tanguy Jousselin‐oba (1) , Masashi Mamada (2) , Karen Wright (1) , Jérome Marrot (1) , Chihaya Adachi (2) , Abderrahim Yassar (3) , Michel Frigoli (1)

1 ILV - Institut Lavoisier de Versailles
2 Kyushu University
3 LPICM - Laboratoire de physique des interfaces et des couches minces [Palaiseau]

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.

Domaines: Chimie organique

Tanguy Jousselin‐oba, Masashi Mamada, Karen Wright, Jérome Marrot, Chihaya Adachi, et al.. Synthesis, Aromaticity and Application of peri-PentacenoPentacene: Localized Representation of Benzenoid Aromatic Compounds. Angewandte Chemie International Edition, In press, ⟨10.1002/anie.202112794⟩. ⟨hal-03442478⟩