Related Experiment Video
Updated: Apr 6, 2026

Facile Preparation and Photoactivation of Prodrug-Dye Nanoassemblies
Published on: February 17, 2023
Stepwise Polychlorination of 8-Chloro-BODIPY and Regioselective Functionalization of 2,3,5,6,8-Pentachloro-BODIPY
Ning Zhao1, Sunting Xuan1, Frank R Fronczek1
1Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, United States.
Abstract:
An effective, stepwise methodology for polychlorination of BODIPY using trichloroisocyanuric acid (TCCA) in acetic acid was developed. In this way, selectively substituted di-, tri-, tetra-, and pentachloro-BODIPYs 2-5 were prepared. The pentachloro-BODIPY is shown to undergo regioselective Pd(0)-catalyzed Stille and Suzuki coupling reactions, first at the 8-position followed by the 3,5- and then the 2,6-positions; nucleophilic substitution reactions occur first at the 8- followed by the 3,5-positions, while the 2,6 are unreactive.
More Related Videos
Related Concept Videos
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
Reactions at the Benzylic Position: Halogenation
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Carboxylic Acids to Acid Chlorides

![[DPEPhosbcpCu]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)