Synthesis of new <i>meso</i>-tetraarylporphyrins bearing cardanol and further transformation of the unsaturated chains

Guo, Ying‐Cen; Xiao, Wen‐Jing; Mele, Giuseppe; Martina, Francesca; Margapoti, Eleonora; Mazzetto, Selma Elaine; Vasapollo, Giuseppe

doi:10.1142/s1088424606000430

Cited by 8 publications

(10 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For instance, the UV-Vis spectrum of 3 showed a Soret band at 419 nm and Q bands at 516, 552, 590 and 646 nm; the UV-Vis spectrum of 4 showed a 1 nm red shift, with a Soret band at 420 nm and Q bands at 517, 553, 591 and 647 nm. A red shift in the Q bands was also observed in the previously reported cardanol-based A 4 -porphyrin [ 16 ]. This suggested to us that the number of the substituents in the porphyrin molecule influences the value of the maximum of absorption in the UV-Vis spectra, producing a red shift when the number of substituents is increased.…”

Section: Resultssupporting

confidence: 74%

“…In the past, we have used 3- n -pentadecylphenol (hydrogenated cardanol), as well as cardanol, as basic materials for the preparation of fine chemicals such as meso- tetrasubstituted cardanol-based A 4 -porphyrins [ 15 , 16 ]; but, we noted that only a few examples concerning the use of 3- n -pentadecyl- phenol-based porphyrins as sensitizers to enhance the photoactivity of TiO 2 in the photodegradation of pollutants in water under UV light, have been reported [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Use of Novel Cardanol-Porphyrin Hybrids and Their TiO2-Based Composites for the Photodegradation of 4-Nitrophenol in Water

et al. 2011

Self Cite

View full text Add to dashboard Cite

Cardanol, a well known hazardous byproduct of the cashew industry, has been used as starting material for the synthesis of useful differently substituted “cardanol-based” porphyrins and their zinc(II), copper(II), cobalt(II) and Fe(III) complexes. Novel composites prepared by impregnation of polycrystalline TiO2 powder with an opportune amount of “cardanol-based” porphyrins, which act as sensitizers for the improvement of the photo-catalytic activity of the bare TiO2, have been used in the photodegradation in water of 4-nitrophenol (4-NP), which is a toxic and bio-refractory pollutant, dangerous for ecosystems and human health.

show abstract

Section: Resultssupporting

confidence: 74%

Section: Introductionmentioning

confidence: 99%

Use of Novel Cardanol-Porphyrin Hybrids and Their TiO2-Based Composites for the Photodegradation of 4-Nitrophenol in Water

et al. 2011

Self Cite

View full text Add to dashboard Cite

show abstract

“…were obtained via mixed aldehyde condensations, using a mixture of two different aldehydes as starting materials. [11][12][13] Asymmetric porphyrins are molecules that exhibit some advantages over the symmetric porphyrins (A4) like: reduced aggregation, groups that allows the use of a wide range of solvents, and presence of dipole moment, which may facilitate the electron injection into the TiO 2 conduction band.…”

Section: Introductionmentioning

confidence: 99%

“…21 It is known that the presence of an alkyl chain or an aryl substituents in porphyrins are important, not just for increase solubility in organic solvents and influence the aggregation of these materials, but also to modify its chemical characteristics and photophysical properties. 11 Here, we report the synthesis and characterization of novel asymmetric cardanol-based A3B porphyrins 4a-d (4a: metal-free, 4b: Ni, 4c: Co, 4d: Cu) as well as the study of their thermal and dielectric properties. Scheme 1 shows the steps and reagents used in the preparation of asymmetric porphyrins.…”

Section: Introductionmentioning

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.

Self Cite

View full text Add to dashboard Cite

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...

show abstract

“…In recent years, among other natural compounds, the use of cardanol to form various new compounds and hybrid compounds has attracted the attention of scientists [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 ]. Cardanol is a renewable and inexpensive organic natural resource that is easily obtained via the vacuum distillation of roasted cashew nut shell liquid (CNSL) obtained from the spongy mesocarp of cashew nut shells.…”

Section: Introductionmentioning

confidence: 99%

Cardanol-Based Materials as Natural Precursors for Olefin Metathesis

2011

Self Cite

View full text Add to dashboard Cite

Cardanol is a renewable, low cost natural material, widely available as a by-product of the cashew industry. It is a mixture of 3-n-pentadecylphenol, 3-(pentadeca-8-enyl)phenol, 3-(pentadeca-8,11-dienyl)phenol and 3-(pentadeca-8,11,14-trienyl)phenol. Olefin metathesis (OM) reaction on cardanol is an important class of reactions that allows for the synthesis of new olefins that are sometime impossible to prepare via other methods. The application of this natural and renewable material to both academic and industrial research will be discussed.

show abstract

Synthesis of new meso-tetraarylporphyrins bearing cardanol and further transformation of the unsaturated chains

Cited by 8 publications

References 2 publications

Use of Novel Cardanol-Porphyrin Hybrids and Their TiO2-Based Composites for the Photodegradation of 4-Nitrophenol in Water

Use of Novel Cardanol-Porphyrin Hybrids and Their TiO2-Based Composites for the Photodegradation of 4-Nitrophenol in Water

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

Cardanol-Based Materials as Natural Precursors for Olefin Metathesis

Contact Info

Product

Resources

About