Related Experiment Video
Updated: Nov 11, 2025
08:51
Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
Published on: October 24, 2017
9.8K
Anthrathiadiazole Derivatives: Synthesis, Physical Properties and Two-photon Absorption
Mingxuan Fan1, Guangsheng Chen1, Yu Xiang1
1School of Chemistry and Environmental Engineering, Key Laboratory for Green Chemical Process of Ministry of Education, Wuhan Institute of Technology, Wuhan, P. R. China.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 29, 2021
Summary
This study introduces a straightforward method to synthesize substituted anthrathiadiazoles, crucial building blocks for advanced materials. These new compounds exhibit tunable properties and significant two-photon absorption, paving the way for novel applications.
Area of Science:
- Organic Chemistry
- Materials Science
- Photophysics
Background:
- Anthrathiadiazole is a vital synthon for constructing large azaacenes.
- Functionalizing anthrathiadiazole is challenging yet essential for diversifying azaacene structures.
- Developing efficient synthetic routes for substituted anthrathiadiazoles is highly desirable.
Purpose of the Study:
- To develop an easy method for synthesizing substituted anthrathiadiazole derivatives.
- To investigate the physical properties and stability of these new compounds.
- To explore the two-photon absorption (TPA) characteristics of the synthesized anthrathiadiazoles.
Main Methods:
- A [4+2] cycloaddition reaction between a,a,a',a'-tetrabromo-o-xylenes derivatives and benzo[c][1,2,5]thiadiazole-4,7-dione.
- Structural characterization of the synthesized anthrathiadiazole derivatives.
- Investigation of physical properties, including stability and oxidation behavior.
- Femtosecond Z-scan technique to measure two-photon absorption (TPA) cross-section values.
Main Results:
- Anthrathiadiazole derivatives with bromo, cyano, and methoxy substituents were successfully synthesized.
- The cyano-substituted derivative (BTH-CN) demonstrated the highest stability.
- The methoxy-substituted derivative (BTH-OCH3) was found to be easily oxidized.
- Synthesized anthrathiadiazoles exhibited large two-photon absorption cross-section values (3000-5000 GM).
- Substituent effects (nature, position, strength) significantly influence TPA properties.
Conclusions:
- A facile [4+2] cycloaddition provides access to functionalized anthrathiadiazoles.
- The synthesized derivatives possess tunable electronic and photophysical properties.
- These compounds hold potential for applications requiring significant two-photon absorption.
More Related Videos
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Related Concept Videos
01:11Aryldiazonium Salts to Azo Dyes: Diazo Coupling
3.3K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
3.3K
01:12Cycloaddition Reactions: MO Requirements for Photochemical Activation
2.3K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.3K
01:29UV–Vis Spectroscopy: Woodward–Fieser Rules
26.9K
UV–Visible absorption spectra of conjugated dienes arise from the lowest energy π → π* transitions. The light-absorbing part of the molecule is called the chromophore, and the substituents directly attached to the chromophore are called auxochromes. A strong correlation exists between the absorption maxima, λmax, and the structure of a conjugated π system. The Woodward–Fieser rules predict the value of λmax for a given structure by adding the...
26.9K
01:26Photochemical Electrocyclic Reactions: Stereochemistry
2.0K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
Selection Rules: Photochemical Activation
2.0K
01:26Thermal and Photochemical Electrocyclic Reactions: Overview
2.6K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
2.6K
01:19Diazonium Group Substitution: –OH and –H
3.0K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
3.0K