Dibenzannulated -acenoacenes from anthanthrene derivatives

• Published in: Chemical science (Cambridge) Vol. 14; no. 37; pp. 1184 - 1193
• Main Authors: Lirette, Frédéric, Darvish, Ali, Zhou, Zheng, Wei, Zheng, Renn, Lukas, Petrukhina, Marina A, Weitz, R. Thomas, Morin, Jean-François
• Format: Journal Article
• Published: 27.09.2023
• ISSN: 2041-6520; 2041-6539
• DOI: 10.1039/d3sc02898d

A series of dibenzannulated phenyl-annulated [4,2] peri -acenoacenes have been synthesized in three straightforward steps from 4,10-dibromoanthanthrone (vat orange 3). The phenyl bisannulation of [4,2] peri -acenoacene provides extra stability by increasing the overall aromatic character of the molecules, and allows for a 45-80% increase of the molar extinction coefficient ( ) compared to their [5,2] peri -acenoacene isomers. Depending on the substituents attached to the π-conjugated core, some derivatives exhibit strong aggregation in the solid state with association constant ( K a ) up to 255 M −1 , resulting in a significant broadening of the absorption spectrum and a substantial decrease of the bandgap value (more than 0.3 V) from solution to the solid state. One [4,2] peri -acenoacene derivative was doubly reduced using cesium and the crystal structure of the resulting salt has been obtained. Field-effect transistors showing a temperature-dependent hole mobility have been tested. A series of dibenzannulated phenyl-annulated [4,2] peri -acenoacenes have been synthesized in three straightforward steps from 4,10-dibromoanthanthrone (vat orange 3).