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Updated: Jun 6, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Demystifying the solvatochromic reversal in Brooker's merocyanine dye
N Arul Murugan1, Jacob Kongsted, Zilvinas Rinkevicius
1Department of Theoretical Chemistry, School of Biotechnology, Royal Institute of Technology, SE-10691 Stockholm, Sweden. murugan@theochem.kth.se
Abstract:
Based on hybrid QM/MM simulation techniques, we rationalize the spectacular solvatochromic reversal behavior observed for a stilbazolium merocyanine (SM) called Brooker's merocyanine dye. This solvatochromic reversal is attributed to a change in the solute π-electron distribution from zwitterionic to neutral following the change in solvents from polar to non polar. Based on our calculations, we suggest that a polar solvent, like water, with larger relative permittivity is influential enough to bring the change in molecular structure from neutral to zwitterionic. Our results clearly indicate that SM exists in a neutral molecular structure in non polar solvents like trichloromethane and thereby we suggest that self-aggregation of SM may not occur in this solvent.
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