Related Experiment Video
Updated: May 7, 2026

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
Published on: April 22, 2016
Photoinduced processes in a dyad made of a linear and an angular perylene bisimide
Lucia Flamigni1, Alberto Zanelli, Heinz Langhals
1Istituto per la Sintesi Organica e Fotoreattivita' (ISOF), CNR, Via P. Gobetti 101, 40129 Bologna, Italy. lucia.flamigni@isof.cnr.it.
Abstract:
A dyad (PI0-PIa) made of a linear (PI0) and an angular (PIa) perylene biscarboximide is synthesized and its spectroscopic, electrochemical and photophysical properties investigated in solvents of various polarity. PIa is characterized by a high intersystem crossing. The spectroscopy and electrochemistry data point to a modest electronic coupling. LUMO-LUMO electron transfer from the singlet excited state PI0-¹PIa is thermodynamically feasible in polar solvents but its occurrence is precluded by a very fast energy transfer to yield ¹PI0-PIa, k(en) ≥ 10(11) s(-1). A HOMO-HOMO electron transfer in the latter state in polar solvents is precluded by the poor driving force, the reaction being unable to compete with the radiative deactivation of the excited state. The efficient energy transfer process is quantitatively examined in the frame of current theories and ascribed to a dipole-dipole (Förster) mechanism.
Related Concept Videos
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Thermal and Photochemical Electrocyclic Reactions: Overview
Pericyclic Reactions: Introduction
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic rearrangements are...
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.
Cycloaddition Reactions: MO Requirements for Photochemical Activation

![[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)