Photophysical Properties of a Substituted Trinaphthylene Synthesized via Palladium-Catalyzed [2 + 2 + 2] Aryne Cyclotrimerization

Abstract Polycyclic aromatic hydrocarbons are fundamental building blocks for organic materials due to their extended π-conjugation and tunable optoelectronic behavior. Among them, trinaphthylenes exhibit remarkable electronic delocalization and structural rigidity, making them attractive candidates for applications in molecular electronics and photonics. In this work, we present an approach to access a novel trinaphthylene derivative through palladium-catalyzed cyclotrimerization of in situ-generated arynes. This transformation leverages a dimethoxynaphthalene precursor, expanding the synthetic utility of these intermediates toward complex aromatic architectures. Comprehensive photophysical studies revealed the luminescent nature of the obtained framework, underscoring its potential as a new platform for the development of organic semiconductors and related optoelectronic materials.

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Publication Details

Journal
Synlett
Published
2026-02-26
DOI
https://doi.org/10.1055/a-2823-7986
Primary Topic
Cyclization and Aryne Chemistry
Type
article
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article

Photophysical Properties of a Substituted Trinaphthylene Synthesized via Palladium-Catalyzed [2 + 2 + 2] Aryne Cyclotrimerization

John F. Bower, Eufrânio N. da Silva Júnior, Luana A. Machado, Guilherme A. M. Jardim et al.
Synlett
Cyclization and Aryne Chemistry
article

Photophysical Properties of a Substituted Trinaphthylene Synthesized via Palladium-Catalyzed [2 + 2 + 2] Aryne Cyclotrimerization

John F. Bower, Eufrânio N. da Silva Júnior, Luana A. Machado, Guilherme A. M. Jardim, Adriano F. Camargo, Craig Robertson
article en

Abstract

Abstract Polycyclic aromatic hydrocarbons are fundamental building blocks for organic materials due to their extended π-conjugation and tunable optoelectronic behavior. Among them, trinaphthylenes exhibit remarkable electronic delocalization and structural rigidity, making them attractive candidates for applications in molecular electronics and photonics. In this work, we present an approach to access a novel trinaphthylene derivative through palladium-catalyzed cyclotrimerization of in situ-generated arynes. This transformation leverages a dimethoxynaphthalene precursor, expanding the synthetic utility of these intermediates toward complex aromatic architectures. Comprehensive photophysical studies revealed the luminescent nature of the obtained framework, underscoring its potential as a new platform for the development of organic semiconductors and related optoelectronic materials.

Synlett
Universidade Federal de Minas Gerais (BR), Centre National de la Recherche Scientifique (FR), University of Liverpool (GB), Centre National pour la Recherche Scientifique et Technique (CNRST) (MA), Centrale Méditerranée (FR)
Openalex Percentile: Top 40%
Cyclization and Aryne Chemistry
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