Related Experiment Video
Updated: Sep 15, 2025

Photoelectron Imaging of Anions Illustrated by 310 Nm Detachment of F−
Published on: July 27, 2018
Orthogonally Arranged π-Electronic Systems with Anion-Responsive Moiety Exhibiting Photoinduced Electron Transfer
Ryuto Toyoshima1, Hiroki Horita1, Shiori Tsuda1
1Department of Applied Chemistry, College of Life Sciences, Ritsumeikan University, Kusatsu 525-8577, Japan.
Abstract:
Orthogonally arranged π-electronic systems comprising directly connected electron-deficient and anion-responsive moieties were synthesized by the connection of acridine/N-methylacridinium and dipyrrolylpyrimidine (dpp) units. Acridine- and N-methylacridinium-substituted dpps showed anion-binding behaviors via hydrogen bonding at pyrrole NH and pyrimidine CH, suggesting the possibility of modulating the electronic states of the anion-responsive π-electronic systems. Transient absorption measurements of the acridine-substituted dpp revealed a photoinduced electron transfer from the anion-responsive unit to the electron-deficient moiety, which was accelerated by anion binding.
Related Concept Videos
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Thermal and Photochemical Electrocyclic Reactions: Overview
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Thermal Electrocyclic Reactions: Stereochemistry
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
π Molecular Orbitals of the Allyl Cation and Anion
Cycloaddition Reactions: MO Requirements for Photochemical Activation

