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Updated: Jan 15, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Influence of Sulfur Oxidation States on the Photophysical Properties of Naphthalimide-Based Donor-Acceptor Systems
Andrés R Urdaneta M1,2, Marcelo Puiatti1,2, Gustavo A Pino1,3,4
1INFIQC: Instituto de Investigaciones en Físico-Química de Córdoba (CONICET-UNC). Haya de la Torre y Medina Allende, Ciudad Universitaria, X5000HUA Córdoba, Argentina.
Abstract:
This study explores the correlation between the photophysical properties and the oxidation state of the sulfur bridge in NI-SOn-PhOMe (n = 0, 1, 2), which connects naphthalimide and p-methoxyphenyl units. The investigations were conducted in solution and in the solid state, with comparisons made to NI-PhOMe, where the two moieties are directly linked via a carbon-carbon bond. In the sulfur-bridged derivatives, aggregation-induced emission (AIE) was observed, the characteristics of which are influenced by intermolecular interactions and the nature of the medium in which insoluble aggregates form. In contrast, NI-PhOMe exhibited conventional solvatochromism typical of donor-acceptor (D-A) push-pull systems. A detailed analysis is presented on the influence of the oxidation state of the sulfur atom on key properties, including the D-A character induced by naphthalimide substitution, as well as the charge transfer (CT) contribution that governs its photophysical behavior.
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