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Dyes: Synthesis, Properties, and Applications
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Dyes: Synthesis, Properties, and Applications

A special issue of Materials (ISSN 1996-1944). This special issue belongs to the section "Materials Chemistry".

Deadline for manuscript submissions: closed (15 December 2021) | Viewed by 12576

Special Issue Editor

Dr. Lucinda V. Reis

E-Mail Website
Guest Editor
Chemistry Research Centre-Vila Real (CQ-VR), University of Trás-os-Montes and Alto Douro, 5000-801 Vila Real, Portugal
Interests: organic synthesis; squarylium cyanine dyes; photodynamic therapy (PDT); NIR probes for biomolecules
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Interest in colored substances has changed radically over time. While until the middle of the last century, the main goals of research were potential applications in the textile and photonic industries, nowadays due to their unique photophysical and photochemical properties, dyes have grown in particular relevance to several fields of science: technology engineering, pharmacology, medicine, and the environment for its application in new forms of renewable energy.

The expansion and unlimited variation that can be made in the base molecular structures of the most diverse classes of dyes in an attempt to enhance and improve their applicability in a given scientific field and/or application has been widely reported in recent studies that demonstrate their broad spectrum of potential uses and their high promise.

Thus, this Special Issue has as its primary challenge the dissemination of information regarding the design and synthesis of new dyes which, regardless of their structure type, should be studied in relation to their photophysical, photochemical, and, when appropriate, photobiological properties in order to prove their relevance in some applications, such as solar organic cell sensitizers, photochromic materials, liquid crystal displays, organic light-emitting devices, organic semiconductors, dye-affinity chromatography for the proteins and enzymes purification, fluorescent sensors and photodynamic therapy photosensitizers. Review articles and communications addressing these topics are also welcome.

Therefore, we kindly invite researchers to submit manuscripts focusing on the topics mentioned above. We would also like to acknowledge in advance all of our colleagues who wish to contribute to this Special Issue: thanks indeed.

Prof. Lucinda V. Reis
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Materials is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2600 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Synthesis of new dyes
  • Physical and chemical properties
  • Photochemical, ecological, or biological studies
  • Structure-activity relationships

Published Papers (4 papers)

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Research

19 pages, 3214 KiB  
Article
Extraction of Natural Dye from Aerial Parts of Argy Wormwood Based on Optimized Taguchi Approach and Functional Finishing of Cotton Fabric
by Faizan Shafiq, Amna Siddique, Md. Nahid Pervez, Mohammad Mahbubul Hassan, Vincenzo Naddeo, Yingjie Cai, Aiqin Hou, Kongliang Xie, Muhammad Qamar Khan and Ick-Soo Kim
Materials 2021, 14(19), 5850; https://0-doi-org.brum.beds.ac.uk/10.3390/ma14195850 - 06 Oct 2021
Cited by 19 | Viewed by 2771
Abstract
The aerial parts of the Argy Worm Wood (AWW) plant have been used in different Chinese foods as a colorant and a taste enhancer for a long time. Despite its application as a food colorant, it has rarely been considered for the coloration [...] Read more.
The aerial parts of the Argy Worm Wood (AWW) plant have been used in different Chinese foods as a colorant and a taste enhancer for a long time. Despite its application as a food colorant, it has rarely been considered for the coloration of textiles. Keeping in mind the variation in color strength due to the change in phytochemical contents by seasonal change and other variables, the extraction of AWW aerial parts was optimized using the Taguchi method. Optimization was performed on the basis of total phytochemical contents (phenols, flavonoids, and tannins) in the extracted solutions. For this purpose, two different solvent systems, namely sodium hydroxide/water (NaOH/water) and ethanol/water (EtOH/water), were applied through a simple aqueous extraction method at varying levels of solvent concentration, and extraction temperature and duration. Maximum phytochemicals yield of 21.96% was obtained using NaOH/water system with 9 g/L NaOH/water at 85 °C for 20 min and 25.5% with 75% aqueous ethanol at 85 °C for 40 min. Optimized extracts were characterized by UV-Vis and FTIR spectrophotometry, which showed the presence of multiple phytochemicals in the extracts. The dyeing temperature and time were also optimized. Dyed cotton fabrics showed medium to high colorfastness to washing and excellent antibacterial and UV radiation absorption properties. The effect of pre-mordanting with salts of iron and copper was also studied on the color fastness properties. Cotton fabrics dyed with two different solvent system extracts displayed various shades of brown with NaOH/water, and green with aqueous ethanol with and without pre-mordanting. The present study provides the textile industry with a promising source of functional bio-colorant and a value-adding approach for the AWW plant industry. Full article
(This article belongs to the Special Issue Dyes: Synthesis, Properties, and Applications)
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19 pages, 5535 KiB  
Article
Substituent and Solvent Polarity on the Spectroscopic Properties in Azo Derivatives of 2-Hydroxynaphthalene and Their Difluoroboranes Complexes
by Agnieszka Skotnicka and Przemysław Czeleń
Materials 2021, 14(12), 3387; https://0-doi-org.brum.beds.ac.uk/10.3390/ma14123387 - 18 Jun 2021
Cited by 1 | Viewed by 1754
Abstract
Novel fluorescent dyes such as difluoroborane complexes of 1-phenylazonaphthalen-2-ol derivatives were successfully synthesized and characterized with a focus on the influence of a substituent and a solvent on the basic photophysical properties. 1H, 11B, 13C, 15N, and 19F [...] Read more.
Novel fluorescent dyes such as difluoroborane complexes of 1-phenylazonaphthalen-2-ol derivatives were successfully synthesized and characterized with a focus on the influence of a substituent and a solvent on the basic photophysical properties. 1H, 11B, 13C, 15N, and 19F nuclear magnetic resonance (NMR) spectra of substituted 1-phenylazonaphthalen-2-ol difluoroboranes and their parent azo dyes were recorded and discussed. The absorption and emission properties of synthesized compounds were investigated in solvents of varying polarity. They were found to be fluorescent despite the presence of the azo group. The azo group rotation was blocked by complexing with -BF2 to get a red shift in absorption. Solvent-dependent spectral properties of compounds were investigated using Lipper-Mataga and Bakhshiev plot. The calculated DFT energies and Frontier Molecular Orbitals calculations of the studied compounds were proved to be consistent with the experimental observations. Full article
(This article belongs to the Special Issue Dyes: Synthesis, Properties, and Applications)
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24 pages, 3024 KiB  
Article
Quinoline- and Benzoselenazole-Derived Unsymmetrical Squaraine Cyanine Dyes: Design, Synthesis, Photophysicochemical Features and Light-Triggerable Antiproliferative Effects against Breast Cancer Cell Lines
by Eurico Lima, Renato E. Boto, Diana Ferreira, José R. Fernandes, Paulo Almeida, Luis F. V. Ferreira, Eliana B. Souto, Amélia M. Silva and Lucinda V. Reis
Materials 2020, 13(11), 2646; https://0-doi-org.brum.beds.ac.uk/10.3390/ma13112646 - 10 Jun 2020
Cited by 18 | Viewed by 3418
Abstract
Photodynamic therapy is an innovative treatment approach broadly directed towards oncological diseases. Its applicability and efficiency are closely related to the interaction of three main components, namely a photosensitizer, light and molecular triplet oxygen, which should drive cell death. Recently, several studies have [...] Read more.
Photodynamic therapy is an innovative treatment approach broadly directed towards oncological diseases. Its applicability and efficiency are closely related to the interaction of three main components, namely a photosensitizer, light and molecular triplet oxygen, which should drive cell death. Recently, several studies have demonstrated that squaraine cyanine dyes have a set of photophysical and photochemical properties that have made of these compounds’ potential photosensitizers for this therapeutic modality. In the present research work, we describe the synthesis and characterization of four quinoline- and benzoselenazole-derived unsymmetrical squaraine cyanine dyes. Except for the precursor of aminosquaraine dyes, i.e., O-methylated derivative, all dyes were evaluated for their behavior and absorption capacity in different organic and aqueous solvents, their ability to form singlet oxygen, their light-stability, and in vitro phototherapeutic effects against two human breast cancer cell cultures (BT-474 and MCF-7). Regardless of the nature of the used solvents, the synthesized dyes showed intense absorption in the red and near-infrared spectral regions, despite the formation of aggregates in aqueous media. Dyes showed high light-stability against light exposure. Despite the low ability to produce singlet oxygen, aminosquaraine dyes demonstrated worthy in vitro phototherapeutic activity. Full article
(This article belongs to the Special Issue Dyes: Synthesis, Properties, and Applications)
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17 pages, 2317 KiB  
Article
Red and Near-Infrared Absorbing Dicyanomethylene Squaraine Cyanine Dyes: Photophysicochemical Properties and Anti-Tumor Photosensitizing Effects
by Tiago D. Martins, Eurico Lima, Renato E. Boto, Diana Ferreira, José R. Fernandes, Paulo Almeida, Luis F. V. Ferreira, Amélia M. Silva and Lucinda V. Reis
Materials 2020, 13(9), 2083; https://0-doi-org.brum.beds.ac.uk/10.3390/ma13092083 - 01 May 2020
Cited by 27 | Viewed by 3761
Abstract
Photodynamic therapy is a medical modality developed for the treatment of several diseases of oncological and non-oncological etiology that requires the presence of a photosensitizer, light and molecular oxygen, which combined will trigger physicochemical reactions responsible for reactive oxygen species production. Given the [...] Read more.
Photodynamic therapy is a medical modality developed for the treatment of several diseases of oncological and non-oncological etiology that requires the presence of a photosensitizer, light and molecular oxygen, which combined will trigger physicochemical reactions responsible for reactive oxygen species production. Given the scarcity of photosensitizers that exhibit desirable characteristics for its potential application in this therapeutic strategy, the main aims of this work were the study of the photophysical and photochemical properties and the photobiological activity of several dicyanomethylene squaraine cyanine dyes. Thus, herein, the study of their aggregation character, photobleaching and singlet oxygen production ability, and the further application of the previously synthesized dyes in Caco-2 and HepG2 cancer cell lines, to evaluate their phototherapeutic effects, are described. Dicyanomethylene squaraine dyes exhibited moderate light-stability and, despite the low singlet oxygen quantum yields, were a core of dyes that exhibited relevant in vitro photodynamic activity, as there was an evident increase in the toxicity of some of the tested dyes exclusive to radiation treatments. Full article
(This article belongs to the Special Issue Dyes: Synthesis, Properties, and Applications)
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