First Example of a Lipophilic Porphyrin-Cardanol Hybrid Embedded in a Cardanol-Based Micellar Nanodispersion

Bloise, Ermelinda; Carbone, Luigi; Colafemmina, Giuseppe; D’Accolti, Lucia; Mazzetto, Selma Elaine; Vasapollo, Giuseppe; Mele, Giuseppe

doi:10.3390/molecules171012252

Cited by 29 publications

(28 citation statements)

References 27 publications

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“…15,16 Some studies mention the synthesis of porphyrins using cardanol as starting material, [17][18][19] which provides interesting lipophilic properties, besides being a substance derived from a renewable raw material, the cashew nut shell liquid (CNSL). 20 Cardanol is a phenolic lipid and the main constituent of the CNSL, a dark oil obtained as a by product from industrial processing of the cashew nut (Anacardium occidentale L.).…”

Section: -13mentioning

confidence: 99%

Synthesis, Characterization and Dielectric Properties of New 5-(4-Hydroxyphenyl)-10,15,20-tri-4-[2-(3-pentadecylphenoxy)ethoxy]phenyl porphyrin and Their Ni, Co and Cu Complexes

Mota¹,

Júnior²,

Ribeiro³

et al. 2016

J. Braz. Chem. Soc.

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New asymmetric cardanol-based porphyrins, free-base and coordinated with Ni, Co and Cu, were synthesized and completely characterized as A3B type. Such porphyrins were obtained aiming improved solubility in polar solvents due insertion of an −OH phenolic group. Their thermal and dielectric properties were also evaluated. Changes in the synthetic route reduced the reaction time and improved the yields of the aldehyde precursor obtainment. Electronic absorption spectra of the new porphyrins in CH 2 Cl 2 , EtOH and acetone, indicated a decrease in the ε (molar absorptivity) values with increasing solvent polarity, except for the nickel complex which, in acetone, showed a slight increase of 2% in the ε value. The dielectric measurements showed that the conductivity (σ) and the loss tangent (tan δ) increased with frequency, but the permittivity (ε') decreased. The results showed that the coordination of the porphyrin promoted a significant change in thermal and dielectric properties, specially for to the Ni-complex compound, which presented the best dielectric properties with interesting values of permittivity and loss tangent at 100 MHz (19.46 and 0.011 a.u., respectively). Keywords: asymmetric porphyrins, cardanol, dielectric properties IntroductionPorphyrins are relatively planar aromatic system consisting of four pyrrole type rings joined by four methynic carbons. They have attracted scientists from many areas due to their biological importance, their fascinating physical, chemical, and spectroscopic properties.1 These compounds have a high electron density due to its 18 π-electrons delocalized on the macrocyclic ring, which are responsible for their spectroscopic characteristics. 2Porphyrin and its derivatives play multiple roles in nature, such as energy transfer and light absorption in a wide range of the electromagnetic spectrum. Such features are of great interest to the industry of optoelectronic components, such as solar cells, due to its ability to act as photosensitizers when irradiated under visible light.3 Thus, this is certainly one of the most promising areas of application for these compounds. The structural modeling and synthesis of new porphyrins has grown exponentially in order to control their electronic and thermal properties. 4 The addition of substituents at the meso positions and metal ions in the center of porphyrins can improve the electrical and magnetic properties, protecting against auto-oxidation and reducing the formation of dimers. However, these structural modifications can promote, in some cases, a significant decrease in their planarity. 5A simple way to obtain porphyrins is the acid catalyzed condensation reaction of pyrrole with specific aldehyde, followed by oxidation of the porphyrinogen. This procedure, originally developed by Rothemund,6 has been refined by [7][8][9] due to the addition of metal salts to the reaction. Despite the modest yields, the relative simplicity of this method has become suited for preparation of large amounts of tetraarylporphyrins. Higher yields an...

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Section: -13mentioning

confidence: 99%

Synthesis, Characterization and Dielectric Properties of New 5-(4-Hydroxyphenyl)-10,15,20-tri-4-[2-(3-pentadecylphenoxy)ethoxy]phenyl porphyrin and Their Ni, Co and Cu Complexes

Mota¹,

Júnior²,

Ribeiro³

et al. 2016

J. Braz. Chem. Soc.

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“…Our twenty years’ experience in green chemistry [18,19,20,21,22,23] has convinced us to extend our studies to the synthesis of bio-polyurethanes [24]. In fact, in our recent work we just reported an efficient, cost-effective, and environmentally safer conversion of soybean oil (SO) into soy-based PU, using as catalyst the molybdenum(VI) dichloride dioxide (MoCl 2 O 2 ) for one-pot synthesis starting from the epoxidized oil (ESO) and with 2,6-tolyl-diisocyanate (TDI).…”

Section: Introductionmentioning

confidence: 99%

Preparation and Characterization of Soybean Oil-Based Polyurethanes for Digital Doming Applications

Pantone¹,

Laurenza

Annese

et al. 2017

Materials

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Polyurethane-resin doming is currently one of the fastest growing markets in the field of industrial graphics and product identification. Semi-rigid bio-based polyurethanes were prepared deriving from soybean oil as a valuable alternative to fossil materials for digital doming and applied to digital mosaic technology. Bio-resins produced can favorably compete with the analogous fossil polymers, giving high-quality surface coatings (ascertained by SEM analyses). In addition, polyurethane synthesis was accomplished by using a mercury- and tin-free catalyst (the commercially available zinc derivative K22) bringing significant benefits in terms of cost efficiency and eco-sustainability.

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“…Cardanol is a renewable and inexpensive organic natural resource that is obtained via the vacuum distillation of roasted cashew nut shell liquid obtained from the spongy mesocarp of cashew nut shells, a byproduct of cashew nut processing . The chemistry of cardanol and its derivatives is becoming an interesting area in academic and industrial research, mainly for the preparation of new eco‐friendly chemicals, composites, and functional organic materials . Indeed cardanol, is a mixture of 3‐n‐pentadecylphenol (20–30%), 3‐(pentadeca‐8‐enyl)phenol (70–80%), 3‐(penta‐deca‐8,11‐dienyl)‐phenol (nearly 5%), and 3‐(pentadeca‐8,11,14‐trienyl) phenol (<5%) .…”

Section: Introductionmentioning

confidence: 99%

“…The chemistry of cardanol and its derivatives is becoming an interesting area in academic and industrial research, mainly for the preparation of new eco‐friendly chemicals, composites, and functional organic materials . Indeed cardanol, is a mixture of 3‐n‐pentadecylphenol (20–30%), 3‐(pentadeca‐8‐enyl)phenol (70–80%), 3‐(penta‐deca‐8,11‐dienyl)‐phenol (nearly 5%), and 3‐(pentadeca‐8,11,14‐trienyl) phenol (<5%) . Specific properties of cardanol and its derivatives, such as the relatively high solubility in nonpolar milieu and good processability, can be attributed to the presence of the ‐C15‐ chain attached to the meta position of the phenolic ring .…”

Section: Introductionmentioning

confidence: 99%

Reactive plasticization of poly(lactide) with epoxy functionalized cardanol

Mihai

Hassouna

Fouquet

et al. 2017

Polymer Engineering & Sci

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New biobased plasticizers made of di‐functional glycidyl ether epoxy cardanol (ECard) were investigated to improve the ductility of renewable poly(lactide) (PLA). Compatibility between PLA and ECard was achieved out through in situ reactive grafting strategy catalyzed with Ethyltriphenyl phosphonium bromide (ETPB) using twin‐screw extruder. In absence of catalyst, ECard forms domain ill‐dispersed in the PLA matrix due to the high incompatibility between both phases. When ETPB is added as catalyst domain size distribution of the plasticizer decreased, indicating an enhanced compatibility due to the reactive grafting of a fraction of ECard plasticizer onto PLA backbone. Although all plasticized PLA specimens exhibit lower glass transition temperature, lower elastic/tensile modulus, lower yield stress, and higher strain at break, the reactive blend containing the lowest amount of catalyst, that is, 0.02 phr, exhibited the highest ductility behavior. POLYM. ENG. SCI., 58:E64–E72, 2018. © 2017 Society of Plastics Engineers

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First Example of a Lipophilic Porphyrin-Cardanol Hybrid Embedded in a Cardanol-Based Micellar Nanodispersion

Cited by 29 publications

References 27 publications

Synthesis, Characterization and Dielectric Properties of New 5-(4-Hydroxyphenyl)-10,15,20-tri-4-[2-(3-pentadecylphenoxy)ethoxy]phenyl porphyrin and Their Ni, Co and Cu Complexes

Synthesis, Characterization and Dielectric Properties of New 5-(4-Hydroxyphenyl)-10,15,20-tri-4-[2-(3-pentadecylphenoxy)ethoxy]phenyl porphyrin and Their Ni, Co and Cu Complexes

Preparation and Characterization of Soybean Oil-Based Polyurethanes for Digital Doming Applications

Reactive plasticization of poly(lactide) with epoxy functionalized cardanol

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