Tetracarboxy‐Functionalized [8]‐, [10]‐, [12]‐, and [14]Phenacenes. Issue 31 (18th August 2017)

• Record Type: Journal Article
• Authors: Moreira, Thamires S.; Ferreira, Marli; Dall'armellina, Alice; Cristiano, Rodrigo; Gallardo, Hugo; Hillard, Elizabeth A.; Bock, Harald; Durola, Fabien
• Is Part Of: European journal of organic chemistry. Issue 31(2017)
• Page Start: 4548
• Page End: 4551
• Publication Date: 2017-08-18
• Subjects: Arenes -- Fused‐ring systems -- Cyclization -- Photooxidation -- Chromophores -- Functional organic materials; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700893
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : The longest known phenacenes so far are constructed efficiently from chrysene and naphthalene diglyoxylic and monoacetic acids by Perkin condensation and photocyclization.