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Organics, Volume 4, Issue 1 (March 2023) – 10 articles

Cover Story (view full-size image): The reaction of the highly electrophilic azo compound MeTAD with bicycloalkadienes via the homo-Diels–Alder reaction provides rapid access to strained heterocycles. These heterocycles serve as precursors to strained azo compounds of both synthetic and theoretical interest. Earlier work by others demonstrated that reaction of MeTAD with unsubstituted, and singly substituted, bicycloalkadienes takes place successfully. However, reaction with 1,2-disubstituted bicycloalkadienes had not yet been explored. Our work demonstrates that disubstitution with the mild electron-withdrawing carboethoxy group permits continued Diels–Alder reactivity, but disubstitution with the very strong electron-withdrawing cyano group prevents reactivity. View this paper
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11 pages, 3271 KiB  
Article
Cell Viability Study of ZnCuInS/ZnS–TPPS4 Conjugates against Different Cell Lines as a Promising Fluorescent Probe
by Ncediwe Tsolekile, Sundararajan Parani, Thabang Calvin Lebepe, Rodney Maluleke, Vuyelwa Ncapayi, Mangaka Clara Matoetoe, Sandile Phinda Songca and Oluwatobi Samuel Oluwafemi
Organics 2023, 4(1), 126-136; https://doi.org/10.3390/org4010010 - 17 Mar 2023
Viewed by 1242
Abstract
In the present work, we report a simple synthetic strategy for fabricating ZnCuInS/ZnS–TPPS4 conjugates and study its cytotoxicity as a promising material for imaging and phototherapy applications. The quaternary QDs were synthesized using eco-friendly materials such as glutathione and water as a [...] Read more.
In the present work, we report a simple synthetic strategy for fabricating ZnCuInS/ZnS–TPPS4 conjugates and study its cytotoxicity as a promising material for imaging and phototherapy applications. The quaternary QDs were synthesized using eco-friendly materials such as glutathione and water as a solvent, while the anionic 10,15,20-(4-sulphonatophenyl) porphyrin (TPPS4) was synthesized via the acidification of a meso-tetraphenylporphyrin precursor. Interest in TPPS4 results from its high-water dispersity, stability, and ability to generate singlet oxygen. Conjugation of ZnCuInS/ZnS QDs with TPPS4 was performed by titrating porphyrin with different amounts of ZnCuInS/ZnS QDs while keeping all other experimental parameters constant. Comparative analysis of the conjugate to the bare QDs and porphyrin revealed enhanced spectral and photophysical properties. Comparative cytotoxicity assays were performed for TPPS4 and ZnCuInS/ZnS–TPPS4 conjugates in BHK21, Hela, A549, Hek 293 and B16-F10 Nex 2 cell lines using the MTT cell viability assay. The results showed negligible in vitro cytotoxicity indicating the conjugate is an excellent and biocompatible candidate for imaging and phototherapy applications. Full article
(This article belongs to the Collection Advanced Research Papers in Organics)
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17 pages, 2780 KiB  
Article
Triple Benefits of Cardanol as Chain Stopper, Flame Retardant and Reactive Diluent for Greener Alkyd Coating
by Maxinne Denis, Cédric Totée, Damien Le Borgne, Rodolphe Sonnier, Sylvain Caillol and Claire Negrell
Organics 2023, 4(1), 109-125; https://doi.org/10.3390/org4010009 - 15 Mar 2023
Cited by 2 | Viewed by 1712
Abstract
Cardanol, a waste from the food industry and widely produced (1 Mt/y), has been used as a chain stopper during the polycondensation of short oil alkyd resins in order to replace benzoic acid. Then, phosphorylated cardanol has been added in order to both [...] Read more.
Cardanol, a waste from the food industry and widely produced (1 Mt/y), has been used as a chain stopper during the polycondensation of short oil alkyd resins in order to replace benzoic acid. Then, phosphorylated cardanol has been added in order to both reduce solvent content and bring flame-retardant (FR) properties to the alkyd resins. The renewable carbon content of the formulations has been increased up to 23%. The impact of the introduction of phosphorylated cardanol molecules on the drying time and flexibility has been studied as well as the thermal and flame-retardant properties by differential scanning calorimeter, thermogravimetric analysis and pyrolysis-combustion flow calorimeter. The most effective flame-retardant coating that was associated with excellent FR properties and excellent coating properties has been obtained with phosphate-cardanol added at 2%wt of P. Indeed, the film properties were closed to the classical alkyd resin, the solvent content was reduced by 50% and the pHRR decreased by 42% compared to the reference alkyd resin. Full article
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12 pages, 2351 KiB  
Article
Looking for a Safe Bridge: Synthesis of P3HT-Bridge-TBO Block-Copolymers and Their Performance in Perovskite Solar Cells
by Aleksandra N. Zhivchikova, Irina V. Klimovich, Maxim E. Sideltsev, Aly Elakshar, Artur T. Kapasharov, Alexander V. Akkuratov, Albert G. Nasibulin, Keith J. Stevenson and Marina M. Tepliakova
Organics 2023, 4(1), 97-108; https://doi.org/10.3390/org4010008 - 27 Feb 2023
Cited by 1 | Viewed by 1817
Abstract
Here, we present a synthesis of three novel conjugated block-copolymers (BCP) with general formula P3HT-bridge-TBO, where P3HT is a poly(3-hexyl)thiophene, TBO is a thiophene-benzothiadiazole block, and the bridge is composed of two fluorene units (FF) or two thiophenes (TT) or a mixture (TF). [...] Read more.
Here, we present a synthesis of three novel conjugated block-copolymers (BCP) with general formula P3HT-bridge-TBO, where P3HT is a poly(3-hexyl)thiophene, TBO is a thiophene-benzothiadiazole block, and the bridge is composed of two fluorene units (FF) or two thiophenes (TT) or a mixture (TF). It is demonstrated that the physicochemical properties of the materials with different bridges are similar. Furthermore, P3HT-bridge-TBO materials are investigated in PSCs with classical n-i-p configuration for the first time. PSCs with BCPs reach average efficiencies with a top of 14.4% for P3HT-FF-TBO. At the same time, devices demonstrate spectacular long-term operation stability after 1000 h under constant illumination with minor changes in efficiency, while PSCs with state-of-the-art hole-transport layer demonstrate unstable behavior. This groundbreaking work demonstrates the potential of BCP to ensure the stable operation of perovskite photovoltaics. Full article
(This article belongs to the Collection Advanced Research Papers in Organics)
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11 pages, 1656 KiB  
Article
Thia-Michael Reaction under Heterogeneous Catalysis
by Giovanna Bosica, Roderick Abdilla and Alessio Petrellini
Organics 2023, 4(1), 86-96; https://doi.org/10.3390/org4010007 - 21 Feb 2023
Viewed by 1743
Abstract
Thia-Michael reactions between aliphatic and aromatic thiols and various Michael acceptors were performed under environmentally-friendly solvent-free conditions using Amberlyst® A21 as a recyclable heterogeneous catalyst to efficiently obtain the corresponding adducts in high yields. Ethyl acrylate was the main acceptor used, although [...] Read more.
Thia-Michael reactions between aliphatic and aromatic thiols and various Michael acceptors were performed under environmentally-friendly solvent-free conditions using Amberlyst® A21 as a recyclable heterogeneous catalyst to efficiently obtain the corresponding adducts in high yields. Ethyl acrylate was the main acceptor used, although others such as acrylamide, linear, and cyclic enones were also utilized successfully. Bifunctional Michael donor, 3-mercaptopropanoic acid, positively furnished the product, albeit in a lower yield and after leaving the reaction to take place for a longer time. The catalyst was easy and safe to handle and successfully recycled for five consecutive cycles. Full article
(This article belongs to the Collection Advanced Research Papers in Organics)
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16 pages, 1912 KiB  
Article
Palladium Catalyzed Ring-Opening of Diazabicylic Olefins with 4-Halo-1,3-Dicarbonyl Compounds: Accessing 3(2H)-Furanone-Appended Cyclopentenes
by Vishnu K. Omanakuttan, Alisha Valsan, Henning Hopf and Jubi John
Organics 2023, 4(1), 70-85; https://doi.org/10.3390/org4010006 - 13 Feb 2023
Viewed by 1174
Abstract
We have realized a Pd-catalyzed ring-opening of diazabicyclic olefins with 4-halo-1,3-dicarbonyl compounds. This reaction resulted in the formation of 3(2H)-furanone-appended hydrazino cyclopentenes. The reaction proceeds via the formation of a π-allylpalladium intermediate which is attacked by the active methylene species, and [...] Read more.
We have realized a Pd-catalyzed ring-opening of diazabicyclic olefins with 4-halo-1,3-dicarbonyl compounds. This reaction resulted in the formation of 3(2H)-furanone-appended hydrazino cyclopentenes. The reaction proceeds via the formation of a π-allylpalladium intermediate which is attacked by the active methylene species, and an intramolecular nucleophilic substitution in the 4-halo-1,3-dicarbonyl moiety furnishes the 3(2H)-furanone-substituted cyclopentene. We could extend this methodology to cyclopropane-appended spirotricyclic olefin for synthesizing 3(2H)-furanone-substituted spiro[2.4]hept-5-ene. Full article
(This article belongs to the Collection Advanced Research Papers in Organics)
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11 pages, 1031 KiB  
Article
Synthesis and Wittig Rearrangement of 3- and 4-Benzyloxyphenylphosphonamidates
by R. Alan Aitken and Ryan A. Inwood
Organics 2023, 4(1), 59-69; https://doi.org/10.3390/org4010005 - 03 Feb 2023
Cited by 2 | Viewed by 1329
Abstract
A series of seven O-ethyl-N-butylphenylphosphonamidates with benzyl ether substituents at the para or meta position have been prepared and fully characterised. Upon treatment with n-butyllithium in THF at RT, these undergo Wittig rearrangement in six cases to give the [...] Read more.
A series of seven O-ethyl-N-butylphenylphosphonamidates with benzyl ether substituents at the para or meta position have been prepared and fully characterised. Upon treatment with n-butyllithium in THF at RT, these undergo Wittig rearrangement in six cases to give the novel phosphonamidate-substituted diarylmethanols in moderate to good yield. Full article
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8 pages, 1364 KiB  
Communication
Parallel Synthesis of Aurones Using a Homogeneous Scavenger
by Zachary E. Taylor and Scott T. Handy
Organics 2023, 4(1), 51-58; https://doi.org/10.3390/org4010004 - 28 Jan 2023
Cited by 1 | Viewed by 1439
Abstract
The ability to synthesize arrays of related compounds quickly and with good purity has become critical for a rapid exploration of their properties for biological or material applications. While a number of methods have been developed to enable this combinatorial synthesis, the existing [...] Read more.
The ability to synthesize arrays of related compounds quickly and with good purity has become critical for a rapid exploration of their properties for biological or material applications. While a number of methods have been developed to enable this combinatorial synthesis, the existing options were not readily appliable to the synthesis of aurones using the simple Knoevenagel condensation approach. In order to avoid the time, expense, and lowered yields associated with flash column chromatography, we developed a scavenging approach for their synthesis. This method uses an excess of aldehyde to ensure complete conversion to aurones, followed by selective removal of the remaining aldehyde using a simple, inexpensive scavenger – isoniazid – and subsequent extraction with dilute acid, to produce the desired compounds with good purity under operationally simple conditions. This approach is expected to be applicable to many other reactions involving aldehydes as one of the reactants. Full article
(This article belongs to the Collection Advanced Research Papers in Organics)
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2 pages, 159 KiB  
Editorial
Acknowledgment to the Reviewers of Organics in 2022
by Organics Editorial Office
Organics 2023, 4(1), 49-50; https://doi.org/10.3390/org4010003 - 19 Jan 2023
Viewed by 786
Abstract
High-quality academic publishing is built on rigorous peer review [...] Full article
8 pages, 1322 KiB  
Article
Exploring the Limits of Reactivity of N-Methyl-1,2,4-triazoline-3,5-dione (MeTAD) with Disubstituted Bicycloalkadienes in the Homo-Diels–Alder Reaction
by Gary W. Breton and Kenneth L. Martin
Organics 2023, 4(1), 41-48; https://doi.org/10.3390/org4010002 - 31 Dec 2022
Viewed by 1349
Abstract
The [2+2+2] cycloaddition (homo-Diels–Alder reaction) of N-substituted 1,2,4-triazoline-3,5-diones (TADs) with bicycloalkadienes produces strained heterocyclic compounds. A reaction with the unsubstituted dienes occurs readily to produce only the expected homo-Diels–Alder adducts. However, previous work in the literature showed that the attachment of a [...] Read more.
The [2+2+2] cycloaddition (homo-Diels–Alder reaction) of N-substituted 1,2,4-triazoline-3,5-diones (TADs) with bicycloalkadienes produces strained heterocyclic compounds. A reaction with the unsubstituted dienes occurs readily to produce only the expected homo-Diels–Alder adducts. However, previous work in the literature showed that the attachment of a single electron-withdrawing group to the diene system results in the formation of not only the expected homo-Diels–Alder adducts, but also interesting “insertion” products. To probe the limits of reactivity of these diene systems, we investigated the reaction of N-methyl-1,2,4-triazoline-3,5-dione (MeTAD) with bicycloalkadienes substituted with two electron-withdrawing groups, i.e., two carbomethoxy or two cyano groups. We hoped to learn whether the reaction still proceeded, and if so, whether the homo-Diels–Alder adducts and/or other types of products were formed. We found that a reaction between MeTAD and the dienes takes place upon substitution with two carbomethoxy groups, albeit at a considerably slower rate than other reactions. The only products observed were the homo-Diels–Alder adducts. However, attachment of two CN groups completely inhibited reactivity. Full article
(This article belongs to the Collection Advanced Research Papers in Organics)
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40 pages, 16239 KiB  
Review
Phenyliodine(III)diacetate (PIDA): Applications in Organic Synthesis
by Ravi Varala, Vittal Seema and Narsimhaswamy Dubasi
Organics 2023, 4(1), 1-40; https://doi.org/10.3390/org4010001 - 23 Dec 2022
Cited by 3 | Viewed by 7546
Abstract
One of the hypervalent iodines most widely used as an oxidizing agent in organic chemistry is (diacetoxyiodo)benzene (PhI(OAc)2), also known as (DAIB), phenyliodine(III) diacetate (PIDA). In this septennial mini-review, the authors have concisely and systematically presented representative applications of PIDA in [...] Read more.
One of the hypervalent iodines most widely used as an oxidizing agent in organic chemistry is (diacetoxyiodo)benzene (PhI(OAc)2), also known as (DAIB), phenyliodine(III) diacetate (PIDA). In this septennial mini-review, the authors have concisely and systematically presented representative applications of PIDA in organic synthesis involving C-H functionalization, hetero-hetero bond formations, heterocyclic ring construction, rearrangements or migrations and miscellaneous reactions along with their interesting mechanistic aspects starting from the summer of 2015 to the present. Full article
(This article belongs to the Collection Advanced Research Papers in Organics)
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