Novel 1,3-bis(p-substituted phenylamino)squaraine dyes. The synthesis and spectroscopic studies

Balcerak, Alicja; Iwińska, Katarzyna; Kabatc, Janina

doi:10.1016/j.dyepig.2019.107596

Cited by 8 publications

(6 citation statements)

References 23 publications

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“…These dyes can exist in three different resonance forms, as neutral, ionic or zwitterionic structure. [69][70][71][72] The general chemical structure of squaraines is presented in Chart 2.…”

Section: Characteristics Of Squaraine Dyesmentioning

confidence: 99%

“…The most commonly used solvents are n-butanol/toluene or 2-propanol/tri-n-butyl orthoformate. Typically, the condensation reactions are performed by heating a reaction mixture under reflux for 16-24 h. 71,73 For example, the basic method of synthesis of 1,3-bis( p-substituted phenylamino)squaraine dyes is presented in Scheme 2. 71 Squaraines are an important and very interesting class of organic functional dyes because of their unique physicochemical properties.…”

Section: Characteristics Of Squaraine Dyesmentioning

confidence: 99%

“…Typically, the condensation reactions are performed by heating a reaction mixture under reflux for 16-24 h. 71,73 For example, the basic method of synthesis of 1,3-bis( p-substituted phenylamino)squaraine dyes is presented in Scheme 2. 71 Squaraines are an important and very interesting class of organic functional dyes because of their unique physicochemical properties. Most of all, squarylium dyes are characterized by strong and sharp absorption extending from ultraviolet (UV), through visible (Vis) to near infrared light (NIR).…”

Section: Characteristics Of Squaraine Dyesmentioning

confidence: 99%

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Recent progress in the development of highly active dyeing photoinitiators based on 1,3-bis(p-substituted phenylamino)squaraines for radical polymerization of acrylates

Balcerak

Kabatc

2022

Polym. Chem.

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Section: Characteristics Of Squaraine Dyesmentioning

confidence: 99%

Section: Characteristics Of Squaraine Dyesmentioning

confidence: 99%

Section: Characteristics Of Squaraine Dyesmentioning

confidence: 99%

See 1 more Smart Citation

Recent progress in the development of highly active dyeing photoinitiators based on 1,3-bis(p-substituted phenylamino)squaraines for radical polymerization of acrylates

Balcerak

Kabatc

2022

Polym. Chem.

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“…After 1 h of heating, an appropriate 6-substituted 2-aminobenzothiazole derivative (5 mmol) was added and the reaction mixture refluxed for additional 4 h. After that, the reaction mixture was cooled and the solvent removed under vacuum. The solid was dried at room temperature [46]. The 2-aminobenzothiazole derivatives were used as photosensitizers in photopolymerization experiments.…”

Section: General Procedures For the Synthesis Of 2-aminobenzothiazole...mentioning

confidence: 99%

“…In 2021, Giacoletto and co-workers [45] presented an overview paper regarding recent advances on squaraine-based photoinitiators. It turns out that squaraines are a promising group of useful dyes for various innovative applications because of their unique features, such as the easiness of the methods of synthesis, the low costs of manufacturing and good photochemical stability [45,46]. For these reasons, the design of novel squaraine acid derivatives seems to be really important.…”

Section: Introductionmentioning

confidence: 99%

High-Performance UV-Vis Light Induces Radical Photopolymerization Using Novel 2-Aminobenzothiazole-Based Photosensitizers

et al. 2021

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The popularity of using the photopolymerization reactions in various areas of science and technique is constantly gaining importance. Light-induced photopolymerization is the basic process for the production of various polymeric materials. The key role in the polymerization reaction is the photoinitiator. The huge demand for radical and cationic initiators results from the dynamic development of the medical sector, and the optoelectronic, paints, coatings, varnishes and adhesives industries. For this reason, we dealt with the subject of designing new, highly-efficient radical photoinitiators. This paper describes novel photoinitiating systems operating in UV-Vis light for radical polymerization of acrylates. The proposed photoinitiators are composed of squaraine (SQ) as a light absorber and various diphenyliodonium (Iod) salts as co-initiators. The kinetic parameters of radical polymerization of trimethylolpropane triacrylate (TMPTA), such as the degree of double bonds conversion (C%), the rate of photopolymerization (Rp), as well as the photoinitiation index (Ip) were calculated. It was found that 2-aminobenzothiazole derivatives in the presence of iodonium salts effectively initiated the polymerization of TMPTA. The rates of polymerization were at about 2 × 10−2 s−1 and the degree of conversion of acrylate groups from 10% to 36% were observed. The values of the photoinitiating indexes for the most optimal initiator concentration, i.e., 5 × 10−3 M were in the range from 1 × 10−3 s−2 even to above 9 × 10−3 s−2. The photoinitiating efficiency of new radical initiators depends on the concentration and chemical structure of used photoinitiator. The role of squaraine-based photoinitiating systems as effective dyeing photoinitiators for radical polymerization is highlighted in this article.

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Synthesis and fluorescence of N-squaraine dianions derived from electron-deficient primary anilines

et al. 2022

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Novel 1,3-bis(p-substituted phenylamino)squaraine dyes. The synthesis and spectroscopic studies

Cited by 8 publications

References 23 publications

Recent progress in the development of highly active dyeing photoinitiators based on 1,3-bis(p-substituted phenylamino)squaraines for radical polymerization of acrylates

Recent progress in the development of highly active dyeing photoinitiators based on 1,3-bis(p-substituted phenylamino)squaraines for radical polymerization of acrylates

High-Performance UV-Vis Light Induces Radical Photopolymerization Using Novel 2-Aminobenzothiazole-Based Photosensitizers

Synthesis and fluorescence of N-squaraine dianions derived from electron-deficient primary anilines

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