Related Experiment Video
Updated: Apr 1, 2026

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
Published on: October 24, 2017
New Aggregation-Induced Emitters: Tetraphenyldistyrylbenzenes
Jan Freudenberg1, Frank Rominger1, Uwe H F Bunz2
1Organisch-Chemisches Institut, Ruprecht-Karls-Universität, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany), Fax: (+49) 6221-54-8401.
Abstract:
The synthesis of five novel distyrylbenzene (DSB) derivatives, featuring a central tetraphenylbenzene core, is reported. The targets show aggregation-induced emission (AIE), which, however, is substituent-dependent. For the pure hydrocarbon and derivatives that do not carry (+M) or (-M) substituents, classic AIE behavior is observed, that is, the DSBs are non-fluorescent in solution, but are highly fluorescent in cold matrices, upon aggregate formation in poor solvents and in the solid, crystalline state. If aldehyde or dibutylamino groups are attached in the para-position of the DSB unit, non-classic AIE-phores result. These are fluorescent both in dilute solution as well as in the solid state. Prolonged irradiation of the targets leads to benzotetraphene derivatives by a double cyclization.
Related Concept Videos
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds
NMR Spectroscopy of Benzene Derivatives
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group...
Thermal and Photochemical Electrocyclic Reactions: Overview
Directing and Steric Effects in Disubstituted Benzene Derivatives
Criteria for Aromaticity and the Hückel 4n + 2 Rule
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as Hückel’s rule or the 4n +...
![[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)
