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Exclusive Feature Papers in Colorants- 2nd Volume

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Colorants".

Deadline for manuscript submissions: closed (31 March 2023) | Viewed by 10716

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Guest Editor
Department of Chemical Sciences, University of Naples “Federico II”, Via Cintia 4, I-80126 Naples, Italy
Interests: structural characterization, extraction, and evaluation/modulation of the antioxidant properties of natural phenolic compounds; exploitation of phenolic compounds, especially from agri-food by-products for the development of functional materials to be used in cosmetics, food packaging, and biomedicine; reactivity of natural phenolic compounds with reactive oxygen and nitrogen species and their manipulation/derivatization to improve their functional properties; evaluation of the antioxidant properties of phenolic compounds and of complex extracts/matrices using validated chemical assays; chemistry of melanin pigments
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Special Issue Information

Dear Colleagues,

We are pleased to announce the Special Issue entitled “Exclusive Feature Papers in Colorants-2nd Volume.” This is a collection of important high-quality papers (original research articles or comprehensive review papers) published in open access format by Editorial Board Members or prominent scholars invited by the Editorial Office and the Guest Editors. This Special Issue aims to discuss new knowledge or new cutting-edge developments in the colorants research field through selected works, in the hope of making a great contribution to the community. We intend for this Special Issue to be the best forum for disseminating excellent research findings as well as sharing innovative ideas in the field.

Prof. Dr. Lucia Panzella
Guest Editor

Manuscript Submission Information

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Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 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.

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Published Papers (6 papers)

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Research

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15 pages, 9693 KiB  
Article
Extended BODIPYs as Red–NIR Laser Radiation Sources with Emission from 610 nm to 750 nm
by Ainhoa Oliden-Sánchez, Enrique Alvarado-Martínez, Diana E. Ramírez-Ornelas, Miguel A. Vázquez, Edurne Avellanal-Zaballa, Jorge Bañuelos and Eduardo Peña-Cabrera
Molecules 2023, 28(12), 4750; https://doi.org/10.3390/molecules28124750 - 13 Jun 2023
Cited by 1 | Viewed by 1294
Abstract
Herein, we report the synthetic access to a set of π-extended BODIPYs featuring a penta-arylated (phenyl and/or thiophene) dipyrrin framework. We take advantage of the full chemoselective control of 8-methylthio-2,3,5,6-tetrabromoBODIPY when we conduct the Liebeskind–Srogl cross-coupling (LSCC) to functionalize exclusively the meso-position, [...] Read more.
Herein, we report the synthetic access to a set of π-extended BODIPYs featuring a penta-arylated (phenyl and/or thiophene) dipyrrin framework. We take advantage of the full chemoselective control of 8-methylthio-2,3,5,6-tetrabromoBODIPY when we conduct the Liebeskind–Srogl cross-coupling (LSCC) to functionalize exclusively the meso-position, followed by the tetra-Suzuki reaction to arylate the halogenated sites. All these laser dyes display absorption and emission bands in the red edge of the visible spectrum reaching the near-infrared with thiophene functionalization. The emission efficiency, both fluorescence and laser, of the polyphenylBODIPYs can be enhanced upon decoration of the peripheral phenyls with electron donor/acceptor groups at para positions. Alternatively, the polythiopheneBODIPYs show an astonishing laser performance despite the charge transfer character of the emitting state. Therefore, these BODIPYs are suitable as a palette of stable and bright laser sources covering the spectral region from 610 nm to 750 nm. Full article
(This article belongs to the Special Issue Exclusive Feature Papers in Colorants- 2nd Volume)
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17 pages, 32975 KiB  
Article
Effects of Different Lengths of Oligo (Ethylene Glycol) Side Chains on the Electrochromic and Photovoltaic Properties of Benzothiadiazole-Based Donor-Acceptor Conjugated Polymers
by Songrui Jia, Shiying Qi, Zhen Xing, Shiyi Li, Qilin Wang and Zheng Chen
Molecules 2023, 28(5), 2056; https://doi.org/10.3390/molecules28052056 - 22 Feb 2023
Cited by 4 | Viewed by 2055
Abstract
In recent years, donor-acceptor (D-A)-type conjugated polymers have been widely used in the field of organic solar cells (OSCs) and electrochromism (EC). Considering the poor solubility of D-A conjugated polymers, the solvents used in material processing and related device preparation are mostly toxic [...] Read more.
In recent years, donor-acceptor (D-A)-type conjugated polymers have been widely used in the field of organic solar cells (OSCs) and electrochromism (EC). Considering the poor solubility of D-A conjugated polymers, the solvents used in material processing and related device preparation are mostly toxic halogenated solvents, which have become the biggest obstacle to the future commercial process of the OSC and EC field. Herein, we designed and synthesized three novel D-A conjugated polymers, PBDT1-DTBF, PBDT2-DTBF, and PBDT3-DTBF, by introducing polar oligo (ethylene glycol) (OEG) side chains of different lengths in the donor unit benzodithiophene (BDT) as side chain modification. Studies on solubility, optics, electrochemical, photovoltaic and electrochromic properties are conducted, and the influence of the introduction of OEG side chains on its basic properties is also discussed. Studies on solubility and electrochromic properties show unusual trends that need further research. However, since PBDT-DTBF-class polymers and acceptor IT-4F failed to form proper morphology under the low-boiling point solvent THF solvent processing, the photovoltaic performance of prepared devices is not ideal. However, films with THF as processing solvent showed relatively desirable electrochromic properties and films cast from THF display higher CE than CB as the solvent. Therefore, this class of polymers has application feasibility for green solvent processing in the OSC and EC fields. The research provides an idea for the design of green solvent-processable polymer solar cell materials in the future and a meaningful exploration of the application of green solvents in the field of electrochromism. Full article
(This article belongs to the Special Issue Exclusive Feature Papers in Colorants- 2nd Volume)
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15 pages, 2765 KiB  
Article
HPLC Study of Product Formed in the Reaction of NBD-Derived Fluorescent Probe with Hydrogen Sulfide, Cysteine, N-acetylcysteine, and Glutathione
by Daniel Słowiński, Małgorzata Świerczyńska, Jarosław Romański and Radosław Podsiadły
Molecules 2022, 27(23), 8305; https://doi.org/10.3390/molecules27238305 - 28 Nov 2022
Cited by 5 | Viewed by 2093
Abstract
Hydrogen sulfide (H2S) and its bioderivatives analogs, such as L-cysteine (L-Cys) and glutathione (GSH), are ubiquitous biological thiols in the physiological and pathological processes of living systems. Their aberrant concentration levels are associated with many diseases. Although several NBD-based fluorescence probes [...] Read more.
Hydrogen sulfide (H2S) and its bioderivatives analogs, such as L-cysteine (L-Cys) and glutathione (GSH), are ubiquitous biological thiols in the physiological and pathological processes of living systems. Their aberrant concentration levels are associated with many diseases. Although several NBD-based fluorescence probes have been developed to detect biological thiols, the HPLC-detection of H2S, GSH, L-Cys, and N-acetylcysteine-specific products has not been described. Herein, a novel NBD-derived pro-coumarin probe has been synthesized and used to develop a new strategy for the triple mode detection of H2S and such thiols as GSH, L-Cys, and NAC. Hydrogen sulfide and those biothiols at physiological pH release fluorescent coumarin from the probe and cause a significant fluorescence enhancement at 473 nm. The appropriate NBD-derived product for H2S, L-Cys, GSH, and NAC has a different color and retention time that allows distinguishing these biological thiols meaning the probe has a great possibility in the biological application. Fluorescent imaging combined with colorimetric and HPLC detection of H2S/biothiol-specific product(s) brings a potential tool for confirming the presence of biological thiols and determining concentrations in various aqueous biological samples. Full article
(This article belongs to the Special Issue Exclusive Feature Papers in Colorants- 2nd Volume)
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9 pages, 1930 KiB  
Article
Novel Yellow Azo Pyridone Derivatives with Different Halide Atoms for Image-Sensor Color Filters
by Sunwoo Park, Yuna Kang, Hyukmin Kwon, Hayeon Kim, Seokwoo Kang, Hayoon Lee, Chun Yoon and Jongwook Park
Molecules 2022, 27(19), 6601; https://doi.org/10.3390/molecules27196601 - 5 Oct 2022
Cited by 3 | Viewed by 1413
Abstract
Novel yellow azo pyridone dye derivatives were synthesized for use in image-sensor color filters. The synthesized compounds have a basic chemical structure composed of azo, hydroxy, amide, and nitrile groups as well as different halide groups. New materials were evaluated on the basis [...] Read more.
Novel yellow azo pyridone dye derivatives were synthesized for use in image-sensor color filters. The synthesized compounds have a basic chemical structure composed of azo, hydroxy, amide, and nitrile groups as well as different halide groups. New materials were evaluated on the basis of their optical, thermal, and surface properties under conditions mimicking those of a commercial device fabrication process. A comparison of their related performance revealed that, among the four prepared compounds, 5-((4,6-dichlorocyclohexa-2,4-dien-1-yl)diazenyl)-6-hydroxy-1,4-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (Cl-PAMOPC) exhibited the best performance as an image-sensor color filter material, including a solubility greater than 0.1 wt% in propylene glycol monomethyl ether acetate solvent, a high decomposition temperature of 263 °C, and stable color difference values of 4.93 and 3.88 after a thermal treatment and a solvent-resistance test, respectively. The results suggest that Cl-PAMOPC can be used as a green dye additive in an image-sensor colorant. Full article
(This article belongs to the Special Issue Exclusive Feature Papers in Colorants- 2nd Volume)
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11 pages, 1615 KiB  
Article
A Straightforward Access to New Amides of the Melanin Precursor 5,6-Dihydroxyindole-2-carboxylic Acid and Characterization of the Properties of the Pigments Thereof
by Rita Argenziano, Marina Della Greca, Lucia Panzella and Alessandra Napolitano
Molecules 2022, 27(15), 4816; https://doi.org/10.3390/molecules27154816 - 27 Jul 2022
Cited by 2 | Viewed by 1453
Abstract
We report herein an optimized procedure for preparation of carboxamides of 5,6-dihydroxyindole-2-carboxylic acid (DHICA), the main biosynthetic precursor of the skin photoprotective agents melanins, to get access to pigments with more favorable solubility properties with respect to the natural ones. The developed procedure [...] Read more.
We report herein an optimized procedure for preparation of carboxamides of 5,6-dihydroxyindole-2-carboxylic acid (DHICA), the main biosynthetic precursor of the skin photoprotective agents melanins, to get access to pigments with more favorable solubility properties with respect to the natural ones. The developed procedure was based on the use of a coupling agent (HATU/DIPEA) and required protection of the catechol function by easily removable acetyl groups. The O-acetylated compounds could be safely stored and taken to the reactive o-diphenol form just before use. Satisfactorily high yields (>85%) were obtained for all amides. The oxidative polymerization of the synthesized amides carried out in air in aqueous buffer at pH 9 afforded melanin-like pigmented materials that showed chromophores resembling those of DHICA-derived pigments, with a good covering of the UVA and the visible region, and additionally exhibited a good solubility in alcoholic solvents, a feature of great interest for the exploitation of these materials as ingredients of dermocosmetic formulations. Full article
(This article belongs to the Special Issue Exclusive Feature Papers in Colorants- 2nd Volume)
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Review

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13 pages, 2262 KiB  
Review
Recent Progress in Research on [2.2]Paracyclophane-Based Dyes
by Wenjing Liu, Huabin Li, Yanmin Huo, Qingxia Yao and Wenzeng Duan
Molecules 2023, 28(7), 2891; https://doi.org/10.3390/molecules28072891 - 23 Mar 2023
Cited by 5 | Viewed by 1639
Abstract
In recent years, the [2.2]paracyclophane (PCP) ring has attracted extensive attention due to its features of providing not only chirality and electron-donating ability but also steric hindrance, which reduces intermolecular π–π stacking interactions and thereby improves the fluorescence properties of dyes. To date, [...] Read more.
In recent years, the [2.2]paracyclophane (PCP) ring has attracted extensive attention due to its features of providing not only chirality and electron-donating ability but also steric hindrance, which reduces intermolecular π–π stacking interactions and thereby improves the fluorescence properties of dyes. To date, some circularly polarized luminescence (CPL)-active small organic molecules based on the PCP skeleton have been reviewed; however, the application of the PCP ring in improving the photophysical properties of fluorescent dyes is still limited, and new molecular design strategies are still required. This review summarizes and promotes the application of PCP in fluorescent dye design, fluorescence detection, and CPL modulation. We expect that this review will provide readers with a comprehensive understanding of the PCP skeleton and lead to further improvement in fluorescent dye design. Full article
(This article belongs to the Special Issue Exclusive Feature Papers in Colorants- 2nd Volume)
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