Synthesis, characterization, energy transfer and photophysical properties of ethynyl bridge linked porphyrin–naphthalimide pentamer and its metal complexes

Xu, Zhijie; Mei, Qunbo; Hua, Qingfang; Tian, Ruqiang; Weng, Jian; Shi, Yujie; Huang, Wei

doi:10.1016/j.molstruc.2015.03.005

Cited by 16 publications

(8 citation statements)

References 40 publications

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“…The emission spectrum from ZnP exhibited a maximum band at 601 nm and a smaller band at 652 nm, with a blue-shift in relation to H 2 P due to influence of the metal. Fluorescence quantum yield values for H 2 P and ZnP were similar (Table 1) and agree with the reported literature [29]. CuP did not exhibit fluorescence under the same conditions.…”

Section: Resultssupporting

confidence: 90%

“…The spectrum exhibits characteristic bands of porphyrins in two distinct regions derived from π → π* transitions of the highly conjugated aromatic porphyrin ring. The most intense band (Soret band) around 400 nm, emerged from transitions of the ground state to the second excited state (S 0 → S 2 ), while bands with molar absorbance magnitude lower (Q bands) between 500–700 nm are assigned to transitions to the first excited state (S 0 → S 1 ) [28,29].…”

Section: Resultsmentioning

confidence: 99%

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Light-Emitting Porphyrin Derivative Obtained from a Subproduct of the Cashew Nut Shell Liquid: A Promising Material for OLED Applications

et al. 2019

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In this work, the meso-tetra[4-(2-(3-n-pentadecylphenoxy)ethoxy]phenylporphyrin (H2P), obtained from the cashew nut shell liquid (CNSL), and its zinc (ZnP) and copper (CuP) metallic complexes, were applied as emitting layers in organic light emitting diodes (OLEDs). These compounds were characterized via optical and electrochemical analysis and the electroluminescent properties of the device have been studied. We performed a cyclic voltammetry analysis to determine the Highest Occupied Molecular Orbital (HOMO) and Lowest Unoccupied Molecular Orbital (LUMO) energy levels for the porphyrins, in order to select the proper materials to assemble the device. H2P and ZnP presented fluorescence emission band in the red region, from 601 nm to 718 nm. Moreover, we verified that the introduction of bulky substituents hinders the π–π stacking, favoring the emission in the film. In addition, the strongest emitter, ZnP, presented a threshold voltage of 4 V and the maximum irradiance of 10 μW cm−2 with a current density (J) of 15 mA cm−2 at 10 V. The CuP complex showed to be a favorable material for the design of OLEDs in the infrared. These results suggest that the porphyrins derived from a renewable source, such as CNSL, is a promising material to be used in organic optoelectronic devices such as OLEDs.

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Section: Resultssupporting

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Light-Emitting Porphyrin Derivative Obtained from a Subproduct of the Cashew Nut Shell Liquid: A Promising Material for OLED Applications

et al. 2019

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“…1000 cm -1 , which further confirmed the formation of metal complexes. 31 Moreover, the presence of aliphatic groups in porphyrins 4a-d, are also evident by the presence of absorbance peaks at 2923 and 2852 cm -1 , which are characteristic of asymmetric and symmetric νC−H modes, respectively. 17 In addition, the compounds exhibit absorption bands of the phenyl groups at ca.…”

Section: Characterizationmentioning

confidence: 97%

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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“…Porphyrins are versatile molecules with optical, photophysical, and electrochemical properties adjustable by peripheral substitution or metallic complexation [ 21 ]. Many efforts have been made towards the development of novel porphyrins to enhance electron transfer efficiency to semicondutors, among which molecules containing mainly carboxyl, sulfonyl, or hydroxyl groups are included [ 22 , 23 , 24 ].…”

Section: Introductionmentioning

confidence: 99%

New ZnO@Cardanol Porphyrin Composite Nanomaterials with Enhanced Photocatalytic Capability under Solar Light Irradiation

et al. 2017

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This work describes the synthesis, characterization, and photocatalytic activity of new composite nanomaterials based on ZnO nanostructures impregnated by lipophlilic porphyrins derived from cashew nut shell liquid (CNSL). The obtained nanomaterials were characterized by X-ray diffraction (XRD), UV-Vis diffuse reflectance spectroscopy (DRS), Fourier transform infrared spectroscopy (FT-IR), transmission electron microscopy (TEM), and steady-state photoluminescence spectra (PL). The results confirm nanostructures showing average diameter of 55 nm and an improved absorption in the visible region. Further, the FTIR analysis proved the existence of non-covalent interactions between the porphyrin molecules and ZnO. The photocatalytic activity of prepared photocatalysts was investigated by degradation of rhodamine B (RhB) in aqueous solution under visible light irradiation and natural sunlight. It was demonstrated that the photocatalytic activity increases in the presence of the porphyrins and, also, depends on the irradiation source. The development of composite photocatalysts based on porphyrins derived from CNSL provides an alternative approach to eliminate efficiently toxic wastes from water under ambient conditions.

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Synthesis, characterization, energy transfer and photophysical properties of ethynyl bridge linked porphyrin–naphthalimide pentamer and its metal complexes

Cited by 16 publications

References 40 publications

Light-Emitting Porphyrin Derivative Obtained from a Subproduct of the Cashew Nut Shell Liquid: A Promising Material for OLED Applications

Light-Emitting Porphyrin Derivative Obtained from a Subproduct of the Cashew Nut Shell Liquid: A Promising Material for OLED Applications

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

New ZnO@Cardanol Porphyrin Composite Nanomaterials with Enhanced Photocatalytic Capability under Solar Light Irradiation

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