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Updated: Jun 20, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Toggling the Oxygen Affinity between Anthracenes and Naphthalenes
Werner Fudickar1, Torsten Linker1
1Department of Chemistry, University of Potsdam, Karl-Liebknecht-Str. 24-25, D-14476, Potsdam, Germany.
Abstract:
We present the design of an anthracenyl-naphthyl (ANT-NAPH) dyad and its application as a luminescent 4-stage photo switch. Both segments can individually react with singlet oxygen to switch off an optical response. In their initial form the larger ANT component reacts significantly faster and thus an ANTO2-NAPH stage is turned on, observed by optical response of the remaining NAPH. To reduce its reactivity, ANT is substituted with two pyridine rings. This concept is first investigated and quantified on ANT and NAPH as separated molecules. Upon protonation the reaction of ANT becomes significantly slower. For the three possible pyridyl isomers this effect increases along the order meta
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