Synthesis, characterization, oxygen electrocatalysis and OFET properties of novel mono- and ball-type metallophthalocyanines

Başak, Ali Sadi; Özkaya, Ali Rıza; Altındal, Ahmet; Salih, Bekir; Şengül, Abdurrahman; Bekâroĝlu, Özer

doi:10.1039/c3dt51955d

Cited by 23 publications

(16 citation statements)

References 31 publications

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“…The dihedral angles between the central isoindole units perylene core to result in a dome-shaped Pc ring and twisting of obtained by DFT at the B3LYP/6-31G level provide preliminary insights into the electronic structures and interactions in this D−A hybrid. 10 According to the calculation, the electron distribution of HOMOs was found to be primarily delocalized over the ZnPc, while the electron distribution of the LUMO was found to be predominantly located on the PDI core as depicted in Fig. 4.…”

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confidence: 88%

“…Fig. 1 The optimized structure of 6 calculated at DFT level of theory 10 using B3LYP/6-31G(d) basis set with LanL2DZ on Zn. The ball and stick presentation of the molecule at the left and the space-filling presentation of the molecule at the right side.…”

Section: Introductionmentioning

confidence: 99%

“…The cyclic-tetramerization of 5 was accomplished by template reaction in the presence of excess of Zn(OAc) 2 ⋅2H 2 O and a base DBU in dry n-pentanol at reflux under argon to yield very dark purple-black powder with 20% yield (Scheme 1). The compound is thermally stable above 400 30 °C, and almost insoluble in common organic solvents, but significantly soluble in coordinating solvents such as DMSO, DMF and pyridine, and no significant metal-ligand interactions are expected due to closed-shell d 10 The first direct evidence for the synthesis of 6 is provided by FT-IR which shows complete disappearance of the cyano stretching at 2232 cm -1 observed in the precursor 5. The experimental and calculated FT-IR spectra are almost identical showing the same 40 pattern of absorption (ESI †, Fig.…”

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confidence: 99%

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A conformationally stressed novel ball-type perylenediimide appended zinc(ii)phthalocyanine hybrid: spectroelectrochemical, electrocolorimetric and photovoltaic properties

et al. 2015

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A supramolecule, 6, based on an electron-donor zinc phthalocyanine (ZnPc) and an electron-acceptor perylene diimide (PDI) has been synthesized and characterized by elemental analysis, UV/Vis, IR, (1)H NMR and solid state (13)C CPMAS NMR and also MALDI-TOF and ICP mass spectrometry. The PDI appended ZnPc core brings about a geometrical constraint in the molecule with intriguing spectroscopic, electrochemical and photovoltaic properties. The first reduction process of 6 occurs on the PDI core while the first oxidation takes place on the Pc ring. These processes reflect a considerably small HOMO-LUMO gap of 1.50 eV, which has vital importance for optoelectronic applications. In addition, the PDI-based first and second reduction processes of 6 are accompanied by an electrochromic behaviour with colour changes from dark purple to blue and blue to turquoise, respectively. A photovoltaic cell involving 6 as the donor and [6,6]-phenyl C61 butyric acid methyl ester as the acceptor has been fabricated. The measurements of the effect of annealing temperature on its performance indicated that the annealing process gives rise to a significant increase in the open circuit voltage, the fill factor and the photoconversion efficiency.

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confidence: 88%

Section: Introductionmentioning

confidence: 99%

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confidence: 99%

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A conformationally stressed novel ball-type perylenediimide appended zinc(ii)phthalocyanine hybrid: spectroelectrochemical, electrocolorimetric and photovoltaic properties

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“…20 We reported a novel peripherally substituted 2, 3,9,10,16,17,23,24-octatosylamino-phthalocyanine which acts as a viable chromogenic anion chemosensor with high affinity towards uoride ions. 21 Suitable modication of Pcs with functional ligands results in a signicant change of their optical properties.…”

Section: Introductionmentioning

confidence: 99%

“…The molecular tolerability via chemical modication and compatibility with the exible substrates of Pcs make them ideal organic semiconductor materials for use as active layers in organic eld effect transistors and photosensitizers in photodynamic therapy (PDT) applications. [10][11][12] Phthalocyanines were employed as active chemosensor materials in the development of electronic conductance, mass-sensitive, surface acousticwave (SAW) and optical sensors. [13][14][15][16] Several studies have investigated their sensing ability by changing both the central metal of the Pc core and the peripheral substituents for effective detection of toxic vapours like NO 2 , NH 3 , SO 2 , ethanol and those containing hazardous metal ions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and photophysical characterization of dimethylamine-derived Zn(ii)phthalocyanines: exploring their potential as selective chemosensors for trinitrophenol

et al. 2015

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We report a novel synthetic approach, with good yields, for the synthesis of selective dimethylaminesubstituted phthalonitriles (1-3) in the presence of triethyl phosphite and dimethylformamide at 160 C.The peripherally modified dimethylamine substituted Zn(II)phthalocyanines (ZnPc1-3) with varied numbers and positions of dimethylamine groups were prepared for a systematic investigation of the effect of the substituents on their electronic and spectroscopic properties. Compounds show strong aggregation behaviour in methanol and this behaviour decreases with the increase of the alkyl chain length of the alcohol solvents (i.e., from methanol to octanol). The fluorescence quantum yields of ZnPc1-3 showed an excellent correlation with the extent of the molecular aggregation. The versatility of the ZnPc1-5 compounds possessing both electron donating and electron withdrawing substituents at their periphery is investigated towards the detection of nitroaromatic compounds (NACs) in solution and in the vapour phase. It was found that ZnPc1-5 exhibit high selectivity towards trinitrophenol (TNP). A good linearity of fluorescence detection using ZnPc3 as the fluorescent probe was observed in the concentration range of 50 Â 10 À6 to 450 Â 10 À6 M in chloroform, with a detection limit (LOD) of 11 AE 2 ppm. Stern-Volmer (SV) and DFT studies reveal that the fluorescence quenching behaviour occurs through photo-induced electron transfer from the excited state of ZnPcs to TNP with static quenching behaviour occurring in a predominant fashion. The formation of a porous morphology of ZnPc3 thin films promotes high selectivity and accessibility to TNP vapours (7.7 Â 10 À3 ppb).

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Dual‐Metal Atom Electrocatalysts: Theory, Synthesis, Characterization, and Applications

Pedersen

Barrio

et al. 2021

Advanced Energy Materials

100

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a required reduction in emissions per unit production of 75% by 2050 in order to have a 50% chance of limiting global mean temperature rise by 2 °C compared to pre-industrial levels. [1,2] Improvements in the field of electrocatalysts, especially in relation to electrolyzers and fuel cells, will help these devices become part of the solution to the looming sustainable energy and chemical production needs. [3] For these devices to be entirely renewable, H 2 (and O 2 ) needs to be produced by water splitting in electrolyzers through H 2 and O 2 evolution (green hydrogen production), rather than from methane reforming (grey hydrogen production). [4,5] H 2 can then be used in electrochemical O 2 reduction in fuel cells to produce electricity. [6,7] Meanwhile, electrochemical reduction of N 2 to NH 3 can provide a sustainable means to a critical fertilization source for the agricultural industry and a carrier for H 2 . [8] Moreover, a way of producing value-added products and a "circular economy" for industry from CO 2 emissions is via the electrocatalytically driven CO 2 reduction, which converts CO 2 to essential feedstocks, such as ethylene or ethanol for the chemical industry. [9] Low-temperature fuel cells and electrolyzers typically utilize catalysts based on platinum group metal (PGM) nanoparticles, [10] which limits device commercialization due to increasing global demand, low uptake of recycling, and high cost of PGMs. [11] Consequently, many researchers have turned their attention to reducing PGM loading or entirely replacing them with lower-cost earth-abundant metals, such as Fe, Cu, Ni, Co, Mn, and, most recently, Sn. [12] Regardless of the catalyst composition, improvements in the electrochemical activity have been highly sought after with two general options available; increasing the number of accessible catalytic sites and/or increasing the intrinsic activity of the catalytic sites. [13] Many different catalyst designs have been explored in order to raise the activity, such as alloying [14] or nanostructuring. [15] While increasing the density of catalytic sites improves activity, this method becomes physically limited when catalyst loading affects charge and mass transport. [13] Thus, improving the activity per catalytic site (intrinsic activity) through controlling local geometry and electronic structure has garnered research attention, with successful methods including shrinking the catalytic site down to atomic scale, as well as locally introducing light heteroatoms or hosting the catalytic site at edges. [10,[16][17][18] Electrochemical clean energy conversion and the production of sustainable chemicals are critical in the journey to realizing a truly sustainable society. To progress electrochemical storage and conversion devices to commercialization, improving the electrocatalyst performance and cost are of utmost importance. Research into dual-metal atom catalysts (DACs) is rising in prominence due to the advantages of these sites over single-metal atom catalysts (SACs), such as breaking scaling ...

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Synthesis, characterization, oxygen electrocatalysis and OFET properties of novel mono- and ball-type metallophthalocyanines

Cited by 23 publications

References 31 publications

A conformationally stressed novel ball-type perylenediimide appended zinc(ii)phthalocyanine hybrid: spectroelectrochemical, electrocolorimetric and photovoltaic properties

A conformationally stressed novel ball-type perylenediimide appended zinc(ii)phthalocyanine hybrid: spectroelectrochemical, electrocolorimetric and photovoltaic properties

Synthesis and photophysical characterization of dimethylamine-derived Zn(ii)phthalocyanines: exploring their potential as selective chemosensors for trinitrophenol

Dual‐Metal Atom Electrocatalysts: Theory, Synthesis, Characterization, and Applications

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