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Novel Hexadeca-Substituted Metal Free and Zinc(II) Phthalocyanines; Design, Synthesis and Photophysicochemical Properties
摘要： The syntheses of a novel 1,4,8,11,15,18,22,25-octahexyloxy-2,3,9,10,16,17,23,24-octa-(4-trifluoromethoxyphenyl) phthalocyanine (3a) and its zinc(II) phthalocyanine derivative (3b) have been described and characterized by elemental analysis, 1H NMR, 13C NMR, 19F NMR, mass, UV-Vis and FT-IR. The newly prepared metal-free phthalocyanine and its zinc(II) counterpart are soluble in most organic solvents. The photophysical and photochemical properties such as aggregation, fluorescence, singlet oxygen generation and photodegradation under light irradiation of these phthalocyanines have been investigated in DMF. The hexadeca-substituted phthalocyanines (3a and 3b) showed longer absorption and emission wavelength values when compared to that of reported phthalocyanine derivatives due to substitution of the all possible positions in the phthalocyanine framework. The zinc(II) phthalocyanine derivative does not only have a good singlet oxygen generation but also has other photophysicochemical properties that enables this phthalocyanine to be useful as a photosensitizer for cancer treatment using photodynamic therapy.
关键词： phthalocyanine,Suzuki-coupling,photodynamic therapy,photochemical,photophysical
更新于2025-09-19 17:15:36
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Pyrenylpyridines: Sky-Blue Emitters for Organic Light-Emitting Diodes
摘要： A novel sky-blue-emitting tripyrenylpyridine derivative, 2,4,6-tri(1-pyrenyl)-pyridine (2,4,6-TPP), has been synthesized using a Suzuki coupling reaction and compared with three previously reported isomeric dipyrenylpyridine (DPP) analogues (2,4-di(1-pyrenyl)pyridine (2,4-DPP), 2,6-di(1-pyrenyl)pyridine (2,6-DPP), and 3,5-di(1-pyrenyl)-pyridine (3,5-DPP)). As revealed by single-crystal X-ray analysis and computational simulations, all compounds possess highly twisted conformations in the solid state with interpyrene torsional angles of 42.3°?57.2°. These solid-state conformations and packing variations of pyrenylpyridines could be correlated to observed variations in physical characteristics such as photo/thermal stability and spectral properties, but showed only marginal influence on electrochemical properties. The novel derivative, 2,4,6-TPP, exhibited the lowest degree of crystallinity as revealed by powder X-ray diffraction analysis and formed amorphous thin films as verified using grazing-incidence wide-angle X-ray scattering. This compound also showed high thermal/photo stability relative to its disubstituted analogues (DPPs). Thus, a nondoped organic light-emitting diode (OLED) prototype was fabricated using 2,4,6-TPP as the emissive layer, which displayed a sky-blue electroluminescence with Commission Internationale de L’Eclairage (CIE) coordinates of (0.18, 0.34). This OLED prototype achieved a maximum external quantum efficiency of 6.0 ± 1.2% at 5 V. The relatively high efficiency for this simple-architecture device reflects a good balance of electron and hole transporting ability of 2,4,6-TPP along with efficient exciton formation in this material and indicates its promise as an emitting material for design of blue OLED devices.
关键词： Suzuki coupling reaction,tripyrenylpyridine derivative,OLED,electroluminescence,dipyrenylpyridine,sky-blue-emitting
更新于2025-09-16 10:30:52
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BODIPY Substituted Zinc(II) Phthalocyanine and Its Bulk Heterojunction Application in the solar cells
摘要： A novel asymmetrical zinc(II) phthalocyanine-BODIPY conjugate (ZnPc-BODIPY) bearing three iodine directly substituted to the macrocycle and one BODIPY connected to macrocycle with amide bond was synthesized by the reaction of carboxylic acid substituted asymmetrical zinc(II) phthalocyanine (ZnPc) with BODIPY derivative bearing amino group (BODIPY-NH2). This conjugate was fully characterized by spectroscopic methods (FT-IR, UV-Vis, 1H NMR, 11B NMR, 19F NMR and mass) and elemental analysis. The fluorescence behavior of ZnPc-BODIPY was studied for determination of energy transfer process. The voltammetry measurements (CV and SWV) were performed for specifying of the HOMO-LUMO energy levels and band gaps of ZnPc-BODIPY and starting compounds ZnPc and BODIPY-NH2 for comparison. In addition, the band gaps of these compounds were also determined by UV-Vis absorption onset (λonset) and theoretical calculations. Bulk heterojunction solar cell containing ZnPc-BODIPY were fabricated in the structure of ITO/PEDOT:PSS/ZnPc-BODIPY:PCBM/Al. The photovoltaic parameters of the solar cell were obtained and ZnPc-BODIPY conjugate was found to bring spectral contribution to IPCE at a peak of 510 nm.
关键词： BODIPY,Organic solar cell,Suzuki coupling,Phthalocyanine
更新于2025-09-12 10:27:22