Related Experiment Video
Updated: Dec 30, 2025

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
Published on: October 24, 2017
Carbazole-Terpyridine Donor-Acceptor Dyads with Rigid π-Conjugated Bridges
Elia Matteucci1, Andrea Baschieri2, Letizia Sambri1
1Dipartimento di Chimica Industriale "Toso Montanari", Università di Bologna, Viale Risorgimento 4, 40136, Bologna, Italy.
Abstract:
A series of molecules in which 9H-carbazole (electron donor, D) and 2,2':6',2''-terpyridine (electron acceptor, A) are connected through rigid π-conjugated bridges (D-π-A systems) have been synthesized and their photophysical properties examined in detail, with the support of DFT calculations. The bridges are made of different sequences of ethynylene, phenylene, and anthracene groups. The synthetic strategies involve condensation of 2-acetylpyridine with the aromatic aldehyde moiety on different functionalized π-conjugated bridges and couplings with carbazole derivatives. The system incorporating anthracene in the bridge shows the typical absorption and emission fingerprints of this polycyclic hydrocarbon. The other systems have HOMOs and LUMOs centred, respectively, over the carbazole and the bridge and exhibit solvatochromic charge-transfer (CT) luminescence with high photoluminescence yield up to 70 %, except when an ethynylene unit is directly attached to the carbazole ring, due to a trans-bent non-emissive π-σ* excited state.
More Related Videos
14:11Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group...
Radicals: Electronic Structure and Geometry
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
Structure of Conjugated Dienes
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
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.