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Synthesis,Aromaticity, and Application of peri-Pentacenopentacene: Localized Representation of Benzenoid Aromatic Compounds
Authors:Tanguy Jousselin-Oba,Masashi Mamada,Karen Wright,J  rome Marrot,Chihaya Adachi,Abderrahim Yassar,Michel Frigoli
Affiliation:Tanguy Jousselin-Oba,Masashi Mamada,Karen Wright,Jérome Marrot,Chihaya Adachi,Abderrahim Yassar,Michel Frigoli
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.
Keywords:acenoacenes  aromaticity  Clar's representation  organic light-emitting diodes  structure elucidation
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