Tetracarboxy-Functionalized [8]-, [10]-, [12]-, and [14]Phenacenes

Thamires S. Moreira (1, 2) , Marli Ferreira (1) , Alice Dall'Armellina (1) , Rodrigo Cristiano (2) , Hugo Gallardo (3) , Elisabeth A. Hillard (1) , Harald Bock (1) , Fabien Durola (1)

1 CRPP - Centre de Recherche Paul Pascal
2 UFPB - Universidade Federal da Paraiba / Federal University of Paraiba
3 Departamento de Quimica [Universidade Federal de Santa Catarina]

Mono- and diglyoxylation of chrysene and naphthalene leads to Perkin reactants that yield bismaleates, which efficiently photocyclize to elongated phenacenetetracarboxylic esters. Their band gaps remain significantly larger than the value postulated for polyphenacene. The reaction with α-branched amines gives the corresponding imides, which are significantly stronger electron acceptors than the esters. The obtained [12]- and [14]phenacenes are the longest [n]phenacenes that have been synthesized to date.

Mots clés: Photooxidation; Cyclization; Arenes; Fused-ring systems; Chromophores; Functional organic materials

Domaines: Matériaux

Thamires S. Moreira, Marli Ferreira, Alice Dall'Armellina, Rodrigo Cristiano, Hugo Gallardo, et al.. Tetracarboxy-Functionalized [8]-, [10]-, [12]-, and [14]Phenacenes. European Journal of Organic Chemistry, 2017, 30 (12), pp. 4548-4551. ⟨10.1002/ejoc.201700893⟩. ⟨hal-01583977⟩