Related Experiment Video
Updated: Nov 17, 2025

Using Cyclic Voltammetry, UV-Vis-NIR, and EPR Spectroelectrochemistry to Analyze Organic Compounds
Published on: October 18, 2018
A Substituent Effect on Two-Photon Absorption of Diphenylacetylene Derivatives with an Electron-Donating/Withdrawing
Tetsuro Ishii1, Tasuku Isozaki1,2, Sho Kinoshita1
1Department of Chemistry and Biological Science, Aoyama Gakuin University, 5-10-1 Fuchinobe, Chuo-ku, Sagamihara, Kanagawa 252-5258, Japan.
Abstract:
Two-photon absorption for diphenylacetylene derivatives with an electron-donating (ED) or electron-withdrawing (EW) group (DPA-Rs) was investigated by high-sensitivity optical-probing photoacoustic spectroscopy. Two-photon absorption spectra and two-photon absorption cross sections σ(2) for DPA-Rs were successfully obtained. Two-photon absorption spectra of DPA-Rs with stronger ED or EW groups display more significant red-shifts and larger σ(2) values. Simulated two-photon absorption spectra, using time-dependent density functional theory within the Tamm-Dancoff approximation, compared well with the experimental spectra. Based on the three-state model, the substituent effect on the two-photon absorption for DPA-Rs was expected to manifest in the transition dipole moments and detuning energies. Information obtained from investigating the monosubstituent effect on two-photon absorption of DPA is critical for an improved understanding of two-photon absorption.
Related Concept Videos
Directing and Steric Effects in Disubstituted Benzene Derivatives
Directing Effect of Substituents: ortho–para-Directing Groups
Substituent Effects on Acidity of Carboxylic Acids
Directing Effect of Substituents: meta-Directing Groups
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

