Tetra and octa substituted Zn(II) and Cu(II) phthalocyanines: Synthesis, characterization and investigation as hole-transporting materials for inverted type-perovskite solar cells

Dalkılıç, Zeynep; Lee, Cheong B.; Choi, Hyosung; Nar, Ilgın; Karatepe, Nilgün; Burat, Ayfer Kalkan

doi:10.1016/j.jorganchem.2020.121419

Cited by 18 publications

(14 citation statements)

References 38 publications

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“…These central metal ions are important in regulating the properties of MPcs. [6] Pcs are of great interest due to the diversity of their interesting optical, electronic and structural properties and serve as active compounds in different fields, especially in materials science and medicine; some of these are liquid crystals, [7] nonlinear optical applications, [8] organic solar cells, [9][10][11] catalyst, [12][13][14] chemical sensors [15] and photodynamic therapy. [16][17][18] Recently, researchers have also studied the antioxidant and antimicrobial activities of Pc molecules.…”

Section: Introductionmentioning

confidence: 99%

“…Pcs are of great interest due to the diversity of their interesting optical, electronic and structural properties and serve as active compounds in different fields, especially in materials science and medicine; some of these are liquid crystals, [7] nonlinear optical applications, [8] organic solar cells, [9–11] catalyst, [12–14] chemical sensors [15] and photodynamic therapy [16–18] …”

Section: Introductionmentioning

confidence: 99%

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Investigation of Biological Activities of Tetra‐substituted Phthalocyanines Bearing Tetraethyleneglycol Monomethyl Ether Chains at Peripheral and Non‐peripheral Positions

et al. 2023

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This study describes the synthesis and characterization of peripherally and non‐peripherally substituted copper(II) and cobalt(II) phthalocyanines bearing tetraethyleneglycol monomethyl ether chains. In addition, the metal‐free and zinc(II) phthalocyanine derivatives were prepared according to the referred procedure. All newly synthesized phthalocyanines were characterized using some spectroscopic techniques such as elemental analysis and fourier transform infrared, ultraviolet‐visible, and mass spectroscopies. The effects of solvent type and concentration on aggregation properties of phthalocyanines were studied, as well. The biological activities of a series of these peripherally and non‐peripherally tetra‐substituted phthalocyanines were investigated. The effects of the central metal ion and the position of the substituent on biological activities of phthalocyanines were also compared. When the antioxidant activities of the synthesized molecules were evaluated by the 2,2‐diphenyl‐1‐picrylhydrazyl method, 1,8/11,15/18,22/25‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy)ethoxy)ethoxy]phthalocyaninatocobalt(II) (63.17±0.012 %) showed the highest activity. The highest reducing power activity was obtained with the 2,9/10,16/17,23/24‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy)ethoxy)ethoxy]phthalocyaninatozinc(II) molecule. In the antibacterial activity studies using the disc diffusion method, 2,9/10,16/17,23/24‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy) ethoxy)ethoxy)ethoxy]phthalocyaninatocopper(II) exhibited the highest inhibition activity on both gram negative (18±0.23 mm) and gram positive (23±0.07 mm) strains. On the other hand, 2,9/10,16/17,23/24‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy) ethoxy)ethoxy]phthalocyaninatozinc(II) and 1,8/11,15/18,22/25‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy)ethoxy)ethoxy]phthalo‐cyaninatozinc(II) compounds presented hemolytic activity against sheep blood in the hemolytic activity studies. The results confirmed that the synthesized molecules demonstrated average antioxidant activity compared to standard antioxidants. 2,9/10,16/17,23/24‐Tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy)ethoxy)ethoxy]phthalo‐cyaninatocopper(II), 2,9/10,16/17,23/24‐tetrakis[2‐(2‐(2‐(2‐methoxy ethoxy)ethoxy)ethoxy)ethoxy]phthalocyaninatozinc(II) and 1,8/11, 15/18,22/25‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy)ethoxy) ethoxy]phthalocyaninatozinc(II) complexes could remarkably inhibit S. aureus and CuPc‐1 complex E. coli growth.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Investigation of Biological Activities of Tetra‐substituted Phthalocyanines Bearing Tetraethyleneglycol Monomethyl Ether Chains at Peripheral and Non‐peripheral Positions

et al. 2023

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“…[22][23][24][25][26][27][28] Due to the ease of the structural modification of Pcs, these macromolecules can be designed for special applications. [29][30][31][32] Additionally, axially substituted phthalocyanines bearing various ligand(s) on the metal center have attracted attention in recent years. [33][34][35][36] Among the axially substituted Pcs, silicon phthalocyanines (SiPcs) exhibit excellent biological properties owing to the unusual six-coordinated silicon (IV) ion and the possibility of symmetrically or unsymmetrically replacement of different axial ligands.…”

Section: Introductionmentioning

confidence: 99%

“…Phthalocyanines (Pcs) are aromatic heterocycles that are well‐known as one of the most potent materials for fundamental and many technological applications such as liquid crystals, electrochromic devices, gas sensors, solar cells, and catalysis [22–28] . Due to the ease of the structural modification of Pcs, these macromolecules can be designed for special applications [29–32] . Additionally, axially substituted phthalocyanines bearing various ligand(s) on the metal center have attracted attention in recent years [33–36] .…”

Section: Introductionmentioning

confidence: 99%

Silicon Phthalocyanines as Anti‐infectious, Antioxidant, and Anticancer Agents

Yenilmez¹,

Farajzadeh²,

Tollu³

et al. 2023

ChemistrySelect

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This study reports the synthesis of three silicon phthalocyanines (SiPc1–3) bearing 2‐dimethylaminoethoxy, 2‐[2‐(dimethylamino)ethoxy]ethoxy, or 2‐{2‐[2‐(dimethylamino)ethoxy]ethoxy}ethoxy on axial positions. Also, their quaternized derivatives (SiPcQ1–3) were prepared. The effect of ligand length on the biological features of water‐soluble silicon phthalocyanines (SiPcQ1–3) was investigated. The highest antimicrobial activity was obtained 32 μg/mL for SiPcQ1 against double‐distilled water, E. hirae, and E. faecalis. The growth inhibition percentages of compounds SiPcQ1–3 were obtained 100 %, 100 %, and 85.14 %, respectively. The highest biofilm inhibition activity was obtained 86.16 % for 250 mg/L SiPcQ3 against S. aureus. The E. coli growth inhibition activities of 50 mg/L compounds SiPcQ1–3 ranged from 60.17 % to 87.53 % and their activities increased (73.46 %–95.37 %) by the enhancement of the concentration. The E. coli viability inhibition activities of SiPcQ1–3 were concentration‐dependent. The DNA cleavage and binding properties of SiPcQ1–3 were studied using pBR322 DNA and CT‐DNA, respectively. Besides, the toxicity of SiPcQ1–3 was examined against the human colon cancer cell line (DLD‐1). The IC50 values of compounds (SiPcQ1–3) were obtained between 10.12 and 27.06 μM in the dark, however, these values were calculated between 12.32 and 22.17 μM under the light. SiPcQ3 exhibited the highest in vitro anticancer activity against the tested cell.

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“…Tuning energy levels of HTMs, especially the HOMO level, can be achieved by modifying HTMs molecular structures to maximize the photovoltaic performance of PSCs [ 7 ]. Numerous studies have been done to fulfill this issue using different techniques such as: structural tuning [ 8 , 9 , 10 , 11 ], changing numbers and positions of attached methoxy groups [ 12 , 13 ], conjugation with more electron-donating moieties [ 14 , 15 , 16 ], replacing the core of spiro-OMeTAD with other electron-rich cores [ 17 , 18 ], attaching aromatic groups onto their peripheral positions [ 19 , 20 ], binary HTMs blending [ 21 ], etc. Fabrication of the first highly efficient PSC was accomplished using the common spiro-OMeTAD as an HTM producing high power conversion efficiency (PCE) > 20%.…”

Section: Introductionmentioning

confidence: 99%

Novel Triarylamine-Based Hole Transport Materials: Synthesis, Characterization and Computational Investigation

Nhari

El‐Shishtawy

et al. 2021

Materials

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Three novel triarylamine-based electron-rich chromophores were synthesized and fully characterized. Compound 1 and Compound 2 were designed with electron-rich triphenylamine skeleton bearing two and four decyloxy groups namely, 3,4-bis(decyloxy)-N,N-diphenylaniline and N-(3,4-bis(decyloxy)phenyl)-3,4-bis(decyloxy)-N-phenylaniline, respectively. The well-known electron-rich phenothiazine was introduced to diphenylamine moiety through a thiazole ring to form N,N-bis(3,4-bis(decyloxy)phenyl)-5-(10H-phenothiazin-2-yl)thiazol−2-amine (Compound 3). These three novel compounds were fully characterized and their UV–vis absorption indicated their transparency as a favorable property for hole transport materials (HTMs) suitable for perovskite solar cells. Cyclic voltammetry measurements revealed that the HOMO energy levels were in the range 5.00–5.16 eV for all compounds, indicating their suitability with the HOMO energy level of the perovskite photosensitizer. Density functional theory (DFT) and time-dependent DFT (TD-DFT) have been used to investigate the possibility of the synthesized compounds to be utilized as HTMs for perovskite solar cells (PSCs). The computational investigation revealed that the hole mobility of Compound 1 was 1.08 × 10–2 cm2 V−1 s−1, and the substitution with two additional dialkoxy groups on the second phenyl ring as represented by Compound 2 significantly boosted the hole mobility to reach the value 4.21 × 10–2 cm2V−1 s−1. On the other hand, Compound 3, in which the third phenyl group was replaced by a thiazole-based phenothiazine, the value of hole mobility decreased to reach 5.93 × 10–5 cm2 V−1 s−1. The overall results indicate that these three novel compounds could be promising HTMs for perovskite solar cells.

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Tetra and octa substituted Zn(II) and Cu(II) phthalocyanines: Synthesis, characterization and investigation as hole-transporting materials for inverted type-perovskite solar cells

Cited by 18 publications

References 38 publications

Investigation of Biological Activities of Tetra‐substituted Phthalocyanines Bearing Tetraethyleneglycol Monomethyl Ether Chains at Peripheral and Non‐peripheral Positions

Investigation of Biological Activities of Tetra‐substituted Phthalocyanines Bearing Tetraethyleneglycol Monomethyl Ether Chains at Peripheral and Non‐peripheral Positions

Silicon Phthalocyanines as Anti‐infectious, Antioxidant, and Anticancer Agents

Novel Triarylamine-Based Hole Transport Materials: Synthesis, Characterization and Computational Investigation

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