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Tetracarboxy‐Functionalized [8]‐, [10]‐, [12]‐, and [14]Phenacenes
Author(s) -
Moreira Thamires S.,
Ferreira Marli,
Dall'armellina Alice,
Cristiano Rodrigo,
Gallardo Hugo,
Hillard Elizabeth A.,
Bock Harald,
Durola Fabien
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700893
Subject(s) - chrysene , chemistry , naphthalene , yield (engineering) , organic chemistry , medicinal chemistry , pyrene , materials science , metallurgy
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.