Rh‐Catalyzed [2 + 2 + 2] Cycloaddition of Linked Bis(Diynes) Ar‐C≡C‐C≡C‐(CH 2 ) 3 ‐C≡C‐C≡C‐Ar With Quinones: Synthesis and Photophysical Properties of Bis(Arylethynyl)‐Naphthoquinones and Anthraquinones
Year: 2026
Type: article
Abstract: ABSTRACT Herein, we report the Rh‐catalyzed [2 + 2 + 2] cycloaddition of linked bis(diynes) Ar‐C≡C‐C≡C‐(CH 2 ) 3 ‐C≡C‐C≡C‐Ar with quinones for the rapid and efficient assembly of rigid structures containing bis(arylethynyl)naphthoquinones or anthraquinones using microwave radiation. The photophysical properties of the products were investigated, including absorption, emission, transient absorption (TA) spectroscopy, and singlet oxygen luminescence studies. However, the quinones did not exhibit photoluminescence or detectable singlet oxygen luminescence. Computational analysis via density functional theory (DFT) was performed to elucidate the electronic and structural factors influencing their behavior. Moreover, reductive methylation of one of the bis(arylethynyl)naphthoquinones ( 3aa ) generated the fluorescent bis(methoxy) naphthalene derivative 4aa ( Φ f = 0.53). However, 4aa underwent photooxidation in air under sunlight via reaction with 1 O 2 , which it sensitized, leading to ring opening of the bis(methoxy)arene ring.
Source: Chemistry - A European Journal
Authors: Luana A. Machado, Jianhua Han, Fábio G. Delolo, Joyce C. Oliveira, Breno U. Abreu, Hállen D. R. Calado, Joannes Krebs, Leibo Tan, Qing Ye, Tobias Groß, Christoph Lambert, Camille Latouche, Abdou Boucekkine, Jean‐François Halet, Holger Braunschweig, Todd B. Marder, Eufrânio N. da Silva Júnior
Institutions: Universidade Federal de Minas Gerais, University of Würzburg, Bavarian Polymer Institute, Centre National de la Recherche Scientifique, Institut Universitaire de France, Institut des Matériaux Jean Rouxel, Université de Nantes, Nantes Université, Institut des Sciences Chimiques de Rennes, École Nationale Supérieure de Chimie de Rennes, Université de Rennes
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,640
Funders: Deutscher Akademischer Austauschdienst, Deutsche Forschungsgemeinschaft, Coordenação de Aperfeiçoamento de Pessoal de Nível Superior, Conselho Nacional de Desenvolvimento Científico e Tecnológico, Fundação de Amparo à Pesquisa do Estado de Minas Gerais, Julius-Maximilians-Universität Würzburg
Awards: G1096969766, G116629194, G1326970997, G13927161, G1606716188, G1761474058, G2090612655, G2203481824, G2430310200, G2823776494, NANOCATALISADORES HETEROBIMETÁLICOS PARA PRODUZIR ANÔDOS ORGÂNICOS PARA BATERIAS DE ?UXO REDOX, REDE DE PESQUISA E INOVAÇÃO PARA BIOENGENHARIA DE NANOSSISTEMAS, G3690646728, INCT DE NANOMATERIAIS DE CARBONO, G3924967235, G4316363450, G5168849808, G5675663293, G6132485245, G6263641072, FOTOCATÁLISE E ESTRATÉGIAS MULTICOMPONENTES DE LIBERAÇÃO DE TENSÃO DE LIGAÇÃO: UMA NOVA VEREDA NA VALORIZAÇÃO DE CO2, USO DE ESTRATÉGIAS MODERNAS PARA A FUNCIONALIZAÇÃO DE COMPOSTOS QUINOIDAIS: INOVAÇÃO TECNOLÓGICA NA OBTENÇÃO DE FÁRMACOS E BATERIAS DE FLUXO REDOX, 500 MHz NMRSpektrometerkonsole, G6815844370, G749042157, G8329556143, G8637253157, NANOCATALISADORES HETEROBIMETÁLICOS PARA PRODUZIR ANÔDOS ORGÂNICOS PARA BATERIAS DE FLUXO REDOX
OpenAlex ID: W7124154250