Related Experiment Video
Updated: Aug 7, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Ab initio investigation of the n --> pi* transitions in thiocarbonyl dyes
Denis Jacquemin1, Valérie Wathelet, Eric A Perpète
1Laboratoire de Chimie Théorique Appliquée, Facultés Universitaires Notre-Dame de la Paix, rue de Bruxelles, 61, B-5000 Namur, Belgium. denis.jacquemin@fundp.ac.be
Abstract:
The n --> pi* transitions in more than 100 thiocarbonyl dyes have been calculated with an ab initio procedure relying on the combination of time-dependent density functional theory (TD-DFT) for evaluating excited states and the polarizable continuum model (PCM) for modeling the bulk solvent effects on both the geometrical and electronic structures. Two hybrid functionals (B3LYP and PBE0) and several basis sets, some including f polarization functions, have been used. B3LYP provides the most accurate raw estimates, but once simple linear regression is performed, both functionals give similar results with a small advantage for PBE0. By use of the latter, the mean absolute deviation with respect to experiment is limited to 0.06 eV whereas less than 20% of the estimates differ from absorption data by more than 0.10 eV. To assess the validity limits of our model, compounds containing multiple C=S chromophores have also been considered.
More Related Videos
Related Concept Videos
2° Amines to N-Nitrosamines: Reaction with NaNO2
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
UV–Vis Spectroscopy: Molecular Electronic Transitions
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Preparation and Reactions of Thiols

