Demystifying the solvatochromic reversal in Brooker's merocyanine dye.
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.
Department of Theoretical Chemistry, School of Biotechnology, Royal Institute of Technology, SE-10691 Stockholm, Sweden. murugan@theochem.kth.se
N Arul
NA
Murugan
Jacob
J
Kongsted
Zilvinas
Z
Rinkevicius
Hans
H
Agren
D001578:Benzopyrans / Q000737:chemistry*; D003116:Color; D004396:Coloring Agents / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D014867:Water / Q000737:chemistry
D001578:Benzopyrans; D004396:Coloring Agents; D007211:Indoles; D012997:Solvents; C548873:merocyanine; D014867:Water