Related Experiment Video

Updated: Sep 21, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

Novel Azocoumarin Derivatives-Synthesis and Characterization

Katarzyna Piechowska¹, Angelika Baranowska-Łączkowska², Krzysztof Z Łączkowski¹

¹Department of Chemical Technology and Pharmaceuticals, Faculty of Pharmacy, Collegium Medicum, Nicolaus Copernicus University, Jurasza 2, 85-089 Bydgoszcz, Poland.

International Journal of Molecular Sciences

|May 28, 2022

Summary

Nine novel thiazolyl-(phenyldiazenyl)-2H-chromen-2-one dyes were synthesized and characterized. These azocoumarin dyes exhibit reversible photoisomerization and potential for use in organic solar cells, with tunable electrochemical and photovoltaic properties.

Area of Science:

Organic Chemistry
Materials Science
Photochemistry

Background:

Azocoumarin derivatives are known for their photoresponsive properties.
Substituent effects on molecular properties are crucial for material design.
Organic dyes are essential components in developing efficient solar cells.

Purpose of the Study:

To synthesize and characterize novel thiazolyl-(phenyldiazenyl)-2H-chromen-2-one dyes.
To investigate the impact of substituents on the dyes' electrochemical, photoisomerization, and photovoltaic properties.
To evaluate the potential of these dyes in bulk-heterojunction and three-component solar cell applications.

Main Methods:

Synthesis and characterization of nine azocoumarin dyes.
Electrochemical analysis to determine redox processes and energy band gaps.
UV illumination studies to investigate photoisomerization in various solvents and solid-state polymer matrices.
Fabrication and testing of bulk-heterojunction and three-component solar cells using the synthesized dyes.

Main Results:

The synthesized dyes are electrochemically active with low energy band gaps (1.71-2.13 eV).
Reversible trans-cis-trans photoisomerization was observed, with slow thermal back-relaxation (up to 7 days in DMF).
Selected dyes showed photovoltaic activity as weak donors in bulk-heterojunction solar cells, with one dye exhibiting promising performance in three-component devices.

Conclusions:

The structure of substituents on the thiazole ring significantly influences the dyes' properties.
These azocoumarin dyes demonstrate potential for applications in organic electronics, particularly in solar energy conversion.
Further optimization of dye structure and device architecture is warranted to enhance photovoltaic performance.

Keywords:

azocoumarine cis-trans thermal relaxation photoisomerization reaction photovoltaic cells

More Related Videos

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Published on: June 13, 2022

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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...

Preparation of 1° Amines: Azide Synthesis

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...

Preparation of 1° Amines: Gabriel Synthesis

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...

Articles linked to this work by shared authors, journal, and citation graph.

Effect of Photoanode Modification with Rare-Earth Metal Oxides on DSSC Performance.

Materials (Basel, Switzerland)·2026

Controlling Photophysical Properties in Bis-Cyclometalated Ir(III)-Terpyridine Complexes through Photoinduced Intraligand Charge Transfer.

Inorganic chemistry·2026

Theoretical and Experimental Study of the Effect of Functional Groups on the Thiazole-5H Proton Chemical Shift in 1H NMR Spectroscopy.

Materials (Basel, Switzerland)·2026

Synergistic Effects of Nanoparticles and Surface Anchoring on Fine-Tuning the Photonic Bandgap in Blue Phase Liquid Crystals.

ACS nano·2026

Copper(II) Complexes with 4-Substituted 2,6-Bis(thiazol-2-yl)pyridines-An Overview of Structural-Optical Relationships.

International journal of molecular sciences·2025

Interpretable Quantitative Structure-Activity Relationship (QSAR) for identification of potent antifungal activity agents towards Candida albicans ATCC 2091.

Molecular diversity·2025

See all related articles