Syntheses of Anthracene-Centered Large PAH Diimides and Conjugated Polymers.
Chemistry
; 28(24): e202104598, 2022 Apr 27.
Article
em En
| MEDLINE
| ID: mdl-35212059
ABSTRACT
Polycyclic aromatic hydrocarbon (PAH) structures with suitable electron-withdrawing groups are useful building blocks for developing optical and electron-transporting materials. Here, we report the application of a double benzannulation process to the syntheses of PAH diimides with enlarged π-frameworks featuring a central anthracene moiety. The preparations are realized by copper-catalyzed [4+2] cycloaddition of ethynyl-substituted aromatic dicarboximide to 2,5-bis(phenylethynyl)terephthalaldehyde, followed by intramolecular photocyclization or direct arylation via Heck cross coupling. A central symmetric benzo[1,2-k4,5-k']-bis(fluoranthene)-3,4,12,13-tetracarboxyl diimide (BFDI) is acquired, with the single crystal structure revealing its completely planar polycyclic skeleton. Such a shape-persistent PAH expectedly exhibits a tendency to stack face-to-face and forms J-aggregates. Moreover, BFDI can be difunctionalized site-selectively at the reactive 9 and 10 positions of the anthracene unit and then applied to prepare conjugated polymers. When coupled with 1,4-diketopyrrolo[3,4-c]-pyrrole (DPP) via thiophene and dithiophene linkers, two polymers with significantly broadened absorption bands extended to the near-infrared regime are obtained, evidencing the effective π-conjugative extension ability of BFDI unit.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Chemistry
Assunto da revista:
QUIMICA
Ano de publicação:
2022
Tipo de documento:
Article