TY - JOUR
T1 - Synthesis, Aromaticity, and Application of peri-Pentacenopentacene
T2 - Localized Representation of Benzenoid Aromatic Compounds
AU - Jousselin-Oba, Tanguy
AU - Mamada, Masashi
AU - Wright, Karen
AU - Marrot, Jérome
AU - Adachi, Chihaya
AU - Yassar, Abderrahim
AU - Frigoli, Michel
N1 - Funding Information:
M.F. and A.Y. acknowledge financial support from the Agence Nationale de la Recherche Grant Number ANR‐16‐CE07‐0024 (GATE). M.M. acknowledges financial support from JST ERATO Grant Number JPMJER1305, JSPS KAKENHI Grant Number 19H02790 and 21H05401, JSPS Core‐to‐Core Program Grant Number JPJSCCA20180005, Inamori Foundation and Iketani Science and Technology Foundation.
Publisher Copyright:
© 2021 Wiley-VCH GmbH
PY - 2022/1/3
Y1 - 2022/1/3
N2 - 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.
AB - 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.
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U2 - 10.1002/anie.202112794
DO - 10.1002/anie.202112794
M3 - Article
C2 - 34727416
AN - SCOPUS:85119623749
SN - 1433-7851
VL - 61
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 1
M1 - e202112794
ER -