Related Experiment Video
Updated: Mar 2, 2026

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
Published on: October 24, 2017
Donor (D)-Acceptor (A) Type Supramolecular Organogelators with Crown Ether-Annulated Tetrathiafulvalene-Pyridazine
Yan Xia1,2, Ruibin Hou1,2, Xiaoyu Liu1
1School of Chemistry and Life Science, Changchun University of Technology, Changchun 130012, People's Republic of China.
Abstract:
T-shaped π-conjugated molecules based on the crown ether-annulated tetrathiafulvalene (TTF)-pyridazine skeleton were prepared, and their gel-forming capacities in various organic solvents were evaluated. The two gelators carrying C14 and C16 alkyl chain units (1b and 1c) displayed efficient gelation in aromatic, polar, and nonpolar solvents owing to the introduced crown ether residue. Stimuli-responsive properties, including temperature sensitivity, redox activity, anion responsiveness, and Na+-dependent behavior, were exhibited by the synthesized gel. Notably, the organogelators easily generated stable charge-transfer complex-based organic gels with 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (T4CNQ) and iodine (I2). In addition, they also showed interaction with a fullerene in toluene system, leading to the formation of a binary gel. Meanwhile, according to scanning electron microscopic (SEM) observation, the xerogels revealed the construction of one-dimensional (1D) helical fibers, two-dimensional (2D) ribbons, and helical ribbons. According to small-angle X-ray scattering (SAXS) analysis results, it was confirmed that the molecules maintained a hexagonal columnar packing structure in the gel phase. These results showed that stacking of columnar tetrathiafulvalene (TTF)-pyridazine cores in the fiber or ribbon provides an efficient pathway for electron conduction.
Related Concept Videos
Crown Ethers
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
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.
Complexation Equilibria: The Chelate Effect
Thermal and Photochemical Electrocyclic Reactions: Overview

