Related Experiment Video
Updated: May 8, 2026

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
Published on: October 24, 2017
Synthesis of a non-aggregating bay-unsubstituted perylene bisimide dye with latent bromo groups for C-C cross
Peter D Frischmann1, Frank Würthner
1Universität Würzburg , Institut für Organische Chemie, Am Hubland, 97074 Würzburg, Germany.
Abstract:
To address the absence of synthetic routes to access easily functionalizable, non-aggregating, and soluble bay-unsubstituted perylene bisimide dyes, an efficient, three-step, multigram-scale synthesis of the divergent building block N,N'-bis(4-bromo-2,6-diisopropylphenyl)perylene-3,4:9,10-tetracarboxylic bisimide is reported. Suzuki coupling yields new dyes that maintain excellent solubility and exhibit unity quantum yields in CHCl3, THF, toluene, and CH3CN. The methodology reported here enables access to dyes with sensitive functional groups such as aldehydes that are not accessible by traditional imidization routes.
More Related Videos
Related Concept Videos
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Radical Substitution: Allylic Bromination
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.
Nucleophilic Aromatic Substitution: Elimination–Addition
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene
![Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F51444.jpg&w=3840&q=50)
