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Advanced Organic Functional Materials
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Advanced Organic Functional Materials

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

Deadline for manuscript submissions: closed (20 January 2023) | Viewed by 18801

Special Issue Editors

Prof. Dr. Grzegorz Mlostoń

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Guest Editor
Department of Organic and Applied Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12, 91-403 Łódź, Poland
Interests: organic synthesis; organic chemistry of sulfur; organic chemistry of fluorine; organic reactions mechanisms; sulfur containing functional materials; homogenous catalysis; drug synthesis and drug delivery
Special Issues, Collections and Topics in MDPI journals
Dr. Marcin Jasiński

E-Mail Website
Guest Editor
Department of Organic and Applied Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12, 91-403 Łódź, Poland
Interests: organic synthesis; reaction mechanisms; cycloadditions; heterocycles; allenes; fluorinated compounds; natural products; total synthesis; organic materials; liquid crystals; stable radicals
Dr. Adam Marek Pieczonka

E-Mail Website
Guest Editor
University of Lodz, Faculty of Chemistry, Department of Organic and Applied Chemistry, Tamka 12, 91-403 Łódź, Poland
Interests: organic chemistry; organic synthesis; asymmetric synthesis; antimicrobial activity; cytotoxicity; photoluminescence; photoluminescent thin films; aggregation induced emission (AIE); electroluminescence; organic electronics; organic light emitting diodes (OLEDs)

Special Issue Information

Dear Colleagues,

The crucial importance of advanced organic functional materials as drivers of technological and societal progress is generally recognized and accepted by the international community of researchers in the natural, medicinal, and technical sciences. In addition, the basic importance of interdisciplinary research has been widely accepted for many decades and it is clearly demonstrated by the rapid development of areas such as informatics, communication and transportation techniques, energy production and storage, medicinal research, etc. Modern organic synthesis plays a crucial role as a driving force of the development of methods applied for the appropriate design and preparation of advanced functional organic materials, which, in many instances, are the result of interdisciplinary-oriented studies and are explored in collaborating physical and medicinal laboratories.

This Special Issue entitled ‘Advanced Organic Functionalized Materials’ welcomes manuscripts presenting results from current studies performed predominately in the research areas pointed out by the keywords given below. However, other related topics are also welcome.

Ionic liquids (ILs): Organic fluids and low melting point materials (<100 °C) composed of ions have been recognized as powerful polar solvents for organic synthesis, which often significantly tune reaction outcomes. Syntheses and applications of ILs, e.g., as green reaction media and bioactive materials, are of current interest.

Liquid crystals: Within a century of the discovery of liquid crystallinity, practical applications of mesogenic molecules, particularly as key components of LC displays, have revolutionized our daily life. Further development in the chemistry and analysis of the thermo- and electro-optic properties of both naturally occurring and synthetic liquid crystals is highly desirable.

Host–guest systems: Inspired by biological systems, host–guest interactions have attracted considerable attention, particularly in the context of chiral molecular recognition. In addition to this hot topic, manuscripts covering studies on different types of noncovalent bonding and the related problems are highly welcome.

Organic nanomaterials: Organic nanomaterials with a controlled morphology and well-defined properties, in many instances, demonstrate unique physical properties, thus opening diverse paths for their useful, practical application. There is a growing demand for the biomedical exploration of organic nanomaterials.

Organic radicals: Open-shell organic molecules attract considerable attention not only as reactive intermediates but also as active structural elements of functional materials exhibiting unique physicochemical properties. The synthesis and characterization of new materials derived from nitroxide, triphenylmethyl, verdazyl, and other persistent radicals are the focus of current, multidisciplinary research.

Radical polymers: Both the development of new therapies aimed at efficient drug delivery and electrochemical energy storage techniques are based on the wide exploration of diverse stable radical polymers (ORPs). In the course of their manufacture, the main challenges are related to their chemical composition and desired structure.

Dyes and pigments: organic photocatalysts: Organic dyes and pigments can be of natural or synthetic origin. Their traditional application is the coloration of diverse materials but current interest is also focused on other applications such as photocatalysis and phototherapy. In the latter case, anticancer and dermatological treatments are the main areas of interest. Numerous, selective photolytic conversions of organic molecules can only be performed in the presence of appropriate photocatalysts, which belong to the class of dyes or pigments. There is a growing number of such reactions reported in the recent literature, and many of them are classified as ‘nature inspired’ organic synthesis.

Photoluminescence: Organic materials with light-emitting properties have attracted growing attention as materials with a broad spectrum of applications in various technological fields. Organic luminogenic materials are widely used as fluorescent sensors or biological probes and show unique advantages in sensitivity, resolution, and the in situ visualization of biological processes.

Electroluminescence: Electroluminescence is a well-known phenomenon that is used in rigid and flexible electronic applications. In recent years, there has been an extremely rapid development in the field of electroluminescent materials for use in new and emerging technologies that could revolutionize illumination technologies.

Organic electronics: Organic compounds gained significant interest due to their broad spectrum of applications as organic semiconductors in organic light emitting diodes (OLEDs), organic field effect transistors (OFET), organic lasers, and other organic electronic devices. Organic electronics is a field of science concerning the design, synthesis, characterization, and application of organic molecules in various technological fields.

Prof. Grzegorz Mlostoń
Dr. Marcin Jasiński
Dr. Adam Marek Pieczonka
Guest Editors

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

  • ionic liquids
  • liquid crystals
  • host–guest systems
  • organic nanomaterials
  • organic radicals
  • radical polymers
  • dyes and pigments
  • organic photocatalysts
  • photoluminescence
  • electroluminescence
  • organic electronics

Published Papers (7 papers)

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Research

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16 pages, 2947 KiB  
Article
Red-Emitting Dithienothiophene S,S-Dioxide Dyes for Cellular Membrane Staining
by Aneta Rzewnicka, Jerzy Krysiak, Róża Pawłowska and Remigiusz Żurawiński
Materials 2023, 16(5), 1806; https://0-doi-org.brum.beds.ac.uk/10.3390/ma16051806 - 22 Feb 2023
Cited by 1 | Viewed by 985
Abstract
A series of dithienothiophene S,S-dioxide (DTTDO) dyes was designed, synthesized, and investigated for their suitability in fluorescent cell imaging. Synthetized (D-π-A-π-D)-type DTTDO derivatives have molecule lengths close to the thickness of the phospholipid membrane, and they contain on [...] Read more.
A series of dithienothiophene S,S-dioxide (DTTDO) dyes was designed, synthesized, and investigated for their suitability in fluorescent cell imaging. Synthetized (D-π-A-π-D)-type DTTDO derivatives have molecule lengths close to the thickness of the phospholipid membrane, and they contain on both ends two positively charged or neutral polar groups to increase their solubility in water and to ensure simultaneous interaction with polar groups of the inner and outer part of the cellular membrane. DTTDO derivatives exhibit absorbance and emission maxima in the 517–538 nm and 622–694 nm range, respectively, and a large Stokes shift up to 174 nm. Fluorescence microscopy experiments revealed that these compounds selectively intercalate into cell membranes. Moreover, a cytotoxicity assay conducted on a model human live cells indicates low toxicity of these compounds at the concentrations required for effective staining. With suitable optical properties, low cytotoxicity, and high selectivity against cellular structures, DTTDO derivatives are proven to be attractive dyes for fluorescence-based bioimaging. Full article
(This article belongs to the Special Issue Advanced Organic Functional Materials)
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13 pages, 2612 KiB  
Article
Novel [FeFe]-Hydrogenase Mimics: Unexpected Course of the Reaction of Ferrocenyl α-Thienyl Thioketone with Fe3(CO)12
by Ahmad Q. Daraosheh, Hassan Abul-Futouh, Natsuki Murakami, Karl Michael Ziems, Helmar Görls, Stephan Kupfer, Stefanie Gräfe, Akihiko Ishii, Małgorzata Celeda, Grzegorz Mlostoń and Wolfgang Weigand
Materials 2022, 15(8), 2867; https://0-doi-org.brum.beds.ac.uk/10.3390/ma15082867 - 14 Apr 2022
Cited by 8 | Viewed by 1945
Abstract
The influence of the substitution pattern in ferrocenyl α-thienyl thioketone used as a proligand in complexation reactions with Fe3(CO)12 was investigated. As a result, two new sulfur–iron complexes, considered [FeFe]-hydrogenase mimics, were obtained and characterized by spectroscopic techniques (1 [...] Read more.
The influence of the substitution pattern in ferrocenyl α-thienyl thioketone used as a proligand in complexation reactions with Fe3(CO)12 was investigated. As a result, two new sulfur–iron complexes, considered [FeFe]-hydrogenase mimics, were obtained and characterized by spectroscopic techniques (1H, 13C{1H} NMR, IR, MS), as well as by elemental analysis and X-ray single crystal diffraction methods. The electrochemical properties of both complexes were studied and compared using cyclic voltammetry in the absence and in presence of acetic acid as a proton source. The performed measurements demonstrated that both complexes can catalyze the reduction of protons to molecular hydrogen H2. Moreover, the obtained results showed that the presence of the ferrocene moiety at the backbone of the linker of both complexes improved the stability of the reduced species. Full article
(This article belongs to the Special Issue Advanced Organic Functional Materials)
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15 pages, 2234 KiB  
Article
Anion Recognition by a Pincer-Type Host Constructed from Two Polyamide Macrocyclic Frameworks Jointed by a Photo-Addressable Azobenzene Switch
by Patryk Niedbała, Magdalena Ceborska, Mart Mehmet, Wiktor Ignacak, Janusz Jurczak and Kajetan Dąbrowa
Materials 2022, 15(2), 692; https://0-doi-org.brum.beds.ac.uk/10.3390/ma15020692 - 17 Jan 2022
Cited by 2 | Viewed by 2550
Abstract
A sterically crowded light-responsive host 1 was synthetized with a 93% yield by applying a post-functionalization protocol utilizing the double amidation of 4,4′-azodibenzoyl dichloride with a readily available 26-membered macrocyclic amine. X-ray structures of two hydrates of trans-1 demonstrate a very [...] Read more.
A sterically crowded light-responsive host 1 was synthetized with a 93% yield by applying a post-functionalization protocol utilizing the double amidation of 4,4′-azodibenzoyl dichloride with a readily available 26-membered macrocyclic amine. X-ray structures of two hydrates of trans-1 demonstrate a very different alignment of the azobenzene linkage, which is involved in T-shape or parallel-displaced π⋯π stacking interactions with the pyridine-2,6-dicarboxamide moieties from the macrocyclic backbone. Despite the rigidity of the macrocyclic framework, which generates a large steric hindrance around the azobenzene chromophore, the host 1 retains the ability to undergo a reversible cis⟷trans isomerization upon irradiation with UVA (368 nm) and blue (410 nm) light. Moreover, thermal cis→trans back-isomerization (ΔG0 = 106.5 kJ∙mol−1, t½ = 141 h) is markedly slowed down as compared to the non-macrocyclic analog. 1H NMR titration experiments in DMSO-d6/0.5% water solution reveal that trans-1 exhibits a strong preference for dihydrogenphosphate (H2PO4−) over other anions (Cl−, MeCO2−, and PhCO2−), whereas the photogenerated metastable cis-1 shows lower affinity for the H2PO4− anion. Full article
(This article belongs to the Special Issue Advanced Organic Functional Materials)
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15 pages, 2688 KiB  
Article
An Experimental and Theoretical Study of Dye Properties of Thiophenyl Derivatives of 2-Hydroxy-1,4-naphthoquinone (Lawsone)
by Matías Monroy-Cárdenas, Oscar Forero-Doria, Ramiro Araya-Maturana and Maximiliano Martínez-Cifuentes
Materials 2021, 14(19), 5587; https://0-doi-org.brum.beds.ac.uk/10.3390/ma14195587 - 26 Sep 2021
Cited by 2 | Viewed by 1892
Abstract
A prospective study of the dye properties of non-toxic lawsone thiophenyl derivatives, obtained using a green synthetic methodology allowed for the description of their bathochromic shifts in comparison to those of lawsone, a well-known natural pigment used as a colorant that recently also [...] Read more.
A prospective study of the dye properties of non-toxic lawsone thiophenyl derivatives, obtained using a green synthetic methodology allowed for the description of their bathochromic shifts in comparison to those of lawsone, a well-known natural pigment used as a colorant that recently also has aroused interest in dye-sensitized solar cells (DSSCs). These compounds exhibited colors close to red, with absorption bands in visible and UV wavelength range. The colorimetric study showed that these compounds exhibited a darker color than that of lawsone within a range of colors depending on the substituent in the phenyl ring. Computational calculations employing Density Functional Theory (DFT) and Time-Dependent Density Functional Theory (TD-DFT), showed that the derivatives have lower excitation energies than lawsone, while the alignment of their frontier orbitals regarding the conduction bands of TiO2 and ZnO and the redox potential of the electrolyte I−/I3− suggests that they could be employed as sensitizers. The study of the interactions of the lawsone and a derivative with a TiO2 surface model by different anchoring modes, showed that the adsorption is thermodynamically favored. Natural bond orbital (NBO) analysis indicates a two-center bonding (BD) O-Ti as the main interaction of the dyes with TiO2. Full article
(This article belongs to the Special Issue Advanced Organic Functional Materials)
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19 pages, 3681 KiB  
Article
Tuning the Surface Properties of Poly(Allylamine Hydrochloride)-Based Multilayer Films
by Justyna Ciejka, Michal Grzybala, Arkadiusz Gut, Michal Szuwarzynski, Krzysztof Pyrc, Maria Nowakowska and Krzysztof Szczubiałka
Materials 2021, 14(9), 2361; https://0-doi-org.brum.beds.ac.uk/10.3390/ma14092361 - 01 May 2021
Cited by 10 | Viewed by 3836
Abstract
The layer-by-layer (LbL) method of polyelectrolyte multilayer (PEM) fabrication is extremely versatile. It allows using a pair of any oppositely charged polyelectrolytes. Nevertheless, it may be difficult to ascribe a particular physicochemical property of the resulting PEM to a structural or chemical feature [...] Read more.
The layer-by-layer (LbL) method of polyelectrolyte multilayer (PEM) fabrication is extremely versatile. It allows using a pair of any oppositely charged polyelectrolytes. Nevertheless, it may be difficult to ascribe a particular physicochemical property of the resulting PEM to a structural or chemical feature of a single component. A solution to this problem is based on the application of a polycation and a polyanion obtained by proper modification of the same parent polymer. Polyelectrolyte multilayers (PEMs) were prepared using the LbL technique from hydrophilic and amphiphilic derivatives of poly(allylamine hydrochloride) (PAH). PAH derivatives were obtained by the substitution of amine groups in PAH with sulfonate, ammonium, and hydrophobic groups. The PEMs were stable in 1 M NaCl and showed three different modes of thickness growth: exponential, mixed exponential-linear, and linear. Their surfaces ranged from very hydrophilic to hydrophobic. Root mean square (RMS) roughness was very variable and depended on the PEM composition, sample environment (dry, wet), and the polymer constituting the topmost layer. Atomic force microscopy (AFM) imaging of the surfaces showed very different morphologies of PEMs, including very smooth, porous, and structured PEMs with micellar aggregates. Thus, by proper choice of PAH derivatives, surfaces with different physicochemical features (growth type, thickness, charge, wettability, roughness, surface morphology) were obtained. Full article
(This article belongs to the Special Issue Advanced Organic Functional Materials)
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10 pages, 6635 KiB  
Article
Oxidation of Cysteinate Anions Immobilized in the Interlamellar Space of CaAl-Layered Double Hydroxide
by Zita Timár, Truong Ngoc Hung, Cora Pravda, Zoltán Kónya, Ákos Kukovecz, Pál Sipos, Gábor Varga and István Pálinkó
Materials 2021, 14(5), 1202; https://0-doi-org.brum.beds.ac.uk/10.3390/ma14051202 - 04 Mar 2021
Cited by 1 | Viewed by 1474
Abstract
L-Cysteinate-intercalated CaAl-layered double hydroxide (LDH) was prepared by the co-precipitation method producing highly crystalline hydrocalumite phase with a well-pillared interlayer gallery. The obtained materials were characterized by X-ray diffractometry, IR as well as Raman spectroscopies. By performing interlamellar oxidation reactions with peracetic acid [...] Read more.
L-Cysteinate-intercalated CaAl-layered double hydroxide (LDH) was prepared by the co-precipitation method producing highly crystalline hydrocalumite phase with a well-pillared interlayer gallery. The obtained materials were characterized by X-ray diffractometry, IR as well as Raman spectroscopies. By performing interlamellar oxidation reactions with peracetic acid as oxidant, oxidation of cysteinate to cystinate in aqueous and cysteinate sulfenic acid in acetonic suspensions occurred. The oxidations could be performed under mild conditions, at room temperature, under neutral pH and in air. It has been shown that the transformation pathways are due to the presence of the layered structure, that is, the confined space of the LDH behaved as molecular reactor. Full article
(This article belongs to the Special Issue Advanced Organic Functional Materials)
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Review

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150 pages, 139433 KiB  
Review
Diels–Alder Cycloaddition with CO, CO2, SO2, or N2 Extrusion: A Powerful Tool for Material Chemistry
by Stanisław Krompiec, Aneta Kurpanik-Wójcik, Marek Matussek, Bogumiła Gołek, Angelika Mieszczanin and Aleksandra Fijołek
Materials 2022, 15(1), 172; https://0-doi-org.brum.beds.ac.uk/10.3390/ma15010172 - 27 Dec 2021
Cited by 2 | Viewed by 4207
Abstract
Phenyl, naphthyl, polyarylphenyl, coronene, and other aromatic and polyaromatic moieties primarily influence the final materials’ properties. One of the synthetic tools used to implement (hetero)aromatic moieties into final structures is Diels–Alder cycloaddition (DAC), typically combined with Scholl dehydrocondensation. Substituted 2-pyranones, 1,1-dioxothiophenes, and, especially, [...] Read more.
Phenyl, naphthyl, polyarylphenyl, coronene, and other aromatic and polyaromatic moieties primarily influence the final materials’ properties. One of the synthetic tools used to implement (hetero)aromatic moieties into final structures is Diels–Alder cycloaddition (DAC), typically combined with Scholl dehydrocondensation. Substituted 2-pyranones, 1,1-dioxothiophenes, and, especially, 1,3-cyclopentadienones are valuable substrates for [4 + 2] cycloaddition, leading to multisubstituted derivatives of benzene, naphthalene, and other aromatics. Cycloadditions of dienes can be carried out with extrusion of carbon dioxide, carbon oxide, or sulphur dioxide. When pyranones, dioxothiophenes, or cyclopentadienones and DA cycloaddition are aided with acetylenes including masked ones, conjugated or isolated diynes, or polyynes and arynes, aromatic systems are obtained. This review covers the development and the current state of knowledge regarding thermal DA cycloaddition of dienes mentioned above and dienophiles leading to (hetero)aromatics via CO, CO2, or SO2 extrusion. Particular attention was paid to the role that introduced aromatic moieties play in designing molecular structures with expected properties. Undoubtedly, the DAC variants described in this review, combined with other modern synthetic tools, constitute a convenient and efficient way of obtaining functionalized nanomaterials, continually showing the potential to impact materials sciences and new technologies in the nearest future. Full article
(This article belongs to the Special Issue Advanced Organic Functional Materials)
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