Tetraiodophthalocyanines: Simple and convenient synthetic protocol and structural modification via Sonogashira cross-coupling reaction

Moiseeva, Ekaterina O.; Kosov, Anton D.; Borisova, Nataliya E.; Tarasevich, B. N.; Dubinina, Tatiana V.; Tomilova, Larisa G.

doi:10.1016/j.ica.2022.120855

Cited by 5 publications

(6 citation statements)

References 71 publications

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“…2(3),9 (10),16 (17),23(24)-tetra-(2-trimethylsilylethynyl) phthalocyaninato zinc (II) (ZnPc) (Scheme S1) was prepared using approach described earlier. [29] Briefly, 2(3),9 (10),16 (17), 23(24)-Tetraiodophthalocyaninato zinc (II) (190 mg, 0.18 mmol), Pd(PPh 3 ) 2 Cl 2 (10 mg, 0.01 mmol, 2 mol %), CuI (3 mg, 0.02 mmol, 4 mol %), and PPh 3 (8 mg, 0.03 mmol, 4 mol %) were placed in an argon-filled Schlenk flask. After the addition of 2 mL of freshly distilled triethylamine and 4 mL of dry THF the mixture was stirred at room temperature for 15 min and (trimethylsilyl)acetylene (40 mg, 0.87 mmol) was added.…”

Section: Methodsmentioning

confidence: 99%

“…Synthesis of photosensitizer . 2(3),9(10),16(17),23(24)‐tetra‐(2‐trimethylsilylethynyl) phthalocyaninato zinc (II) (ZnPc) (Scheme S1) was prepared using approach described earlier [29] . Briefly, 2(3),9(10),16(17),23(24)‐Tetraiodophthalocyaninato zinc (II) (190 mg, 0.18 mmol), Pd(PPh 3 ) 2 Cl 2 (10 mg, 0.01 mmol, 2 mol %), CuI (3 mg, 0.02 mmol, 4 mol %), and PPh 3 (8 mg, 0.03 mmol, 4 mol %) were placed in an argon‐filled Schlenk flask.…”

Section: Methodsmentioning

confidence: 99%

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Coupling of Phthalocyanines with Plasmonic Gold Nanoparticles by Click Chemistry for an Enhanced Singlet Oxygen Based Photoelectrochemical Sensing

Khan,

Matshitse,

Borah

et al. 2024

ChemElectroChem

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Coupling photosensitizers (PSs) with plasmonic nanoparticles increases the photocatalytic activity of PSs as the localized surface plasmon resonance (LSPR) of plasmonic nanoparticles leads to extreme concentration of light in their vicinity known as the near‐field enhancement effect. To realize this in a colloidal phase, efficient conjugation of the PS molecules with the plasmonic nanoparticle surface is critical. In this work, we demonstrate the coupling of phthalocyanine (Pc) molecules with gold nanoparticles (AuNPs) in the colloidal phase via click chemistry. This conjugated Pc‐AuNPs colloidal system is shown to enhance the photocatalytic singlet oxygen (1O2) production over non‐conjugated Pcs and hence improve the photoelectrochemical detection of phenols. The plasmonic enhancement of the 1O2 generation by Pcs was clearly elucidated by complementary experimental and computational classical electromagnetic models. The dependence of plasmonic enhancement on the spectral position of the excitation laser wavelength and the absorbance of the Pc molecules with respect to the wavelength specific near‐field enhancement is clearly demonstrated. A high ∼ 8 times enhancement is obtained with green laser (532 nm) at the LSPR due to the maximum near‐field enhancement at the resonance wavelength.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Coupling of Phthalocyanines with Plasmonic Gold Nanoparticles by Click Chemistry for an Enhanced Singlet Oxygen Based Photoelectrochemical Sensing

Khan,

Matshitse,

Borah

et al. 2024

ChemElectroChem

Self Cite

View full text Add to dashboard Cite

show abstract

“…2(3),9(10),16(17),23(24)-tetra-(2-trimethylsilylethynyl) phthalocyaninato zinc (II) (ZnPc) (Scheme S1) was prepared using approach described earlier. 27 Briefly, 2(3),9(10),16(17),23(24)-Tetraiodophthalocyaninato zinc (II) (190 mg, 0.18 mmol), Pd(PPh3)2Cl2 (10 mg, 0.01 mmol, 2 mol %), CuI (3 mg, 0.02 mmol, 4 mol %), and PPh3 (8 mg, 0.03 mmol, 4 mol %) were placed in an argon-filled Schlenk flask. After the addition of 2 mL of freshly distilled triethylamine and 4 mL of dry THF the mixture was stirred at room temperature for 15 min and (trimethylsilyl)acetylene (40 mg, 0.87 mmol) was added.…”

Section: Methodsmentioning

confidence: 99%

Coupling of phthalocyanines with plasmonic gold nanoparticles by click chemistry for an enhanced singlet oxygen based photoelectrochemical sensing

Khan,

Matshitse,

Borah

et al. 2023

Preprint

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Coupling photosensitizers (PSs) with plasmonic nanoparticles increases the photocatalytic activity of PSs as the localized surface plasmon resonance (LSPR) of plasmonic nanoparticles leads to extreme concentration of light in their vicinity known as the near-field enhancement effect. To realize this in a colloidal phase, efficient conjugation of the PS molecules with the plasmonic nanoparticle surface is critical. In this work, we demonstrate the coupling of phthalocyanine (Pc) molecules with gold nanoparticles (AuNPs) in the colloidal phase via click chemistry. This conjugated Pc-AuNPs colloidal system is shown to enhance the photocatalytic singlet oxygen (1O2) production over non-conjugated Pcs and hence improve the photoelectrochemical detection of phenols. The plasmonic enhancement of the 1O2 generation by Pcs was clearly elucidated by complementary experimental and computational classical electromagnetic models. The dependence of plasmonic enhancement on the spectral position of the excitation laser wavelength and the absorbance of the Pc molecules with respect to the wavelength specific near-field enhancement is clearly demonstrated. A high ∼ 8 times enhancement is obtained with green laser (532 nm) at the LSPR due to the maximum near-field enhancement at the resonance wavelength.

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“…Moiseeva et al succeeded in synthesizing 1.9 grams of 2(3),9 (10),16 (17), 23(24)-tetraiodophthalocyanine MW10 in a single batch by irradiating a mixture of 4-iodophthalonitrile and Zn(quinoline) 2 Cl 2 salt in a microwave reactor at 150 W for 7 minutes. [43] The authors achieved a high 83 % yield at analytical grade (� 98 %) purity. This result is promising as this molecule is a versatile intermediate, whose iodide atoms can be widely substituted by exploiting the rich palladium-catalyzed chemistry to provide functionalized derivatives with high complexity.…”

Section: Microwave Irradiationmentioning

confidence: 95%

“…[39,40] This approach is by far the most represented green synthetic method in literature for the synthesis of phthalocyanines. Microwaveassisted synthesis has successfully provided macrocycles functionalized with halides, [41][42][43][44] terminal alkynes, [45] crown ethers, [46] substituted phenoxy [47][48][49] and 1-naphthyloxy [50] groups, tetraaza, [51] tetraoxamonoaza, [52] tetrathiacyclohexadecane, [53] dithiadiazadioxa, [54] diazadithio [55] and tetrathiadiaza rings, [56,57] thiazoles, [58] functionalized triazoles, [59][60][61][62] phenylthioethanol, [63] monoterpenes like (1R)-(À ) myrtenol and (1R,2S,5R)-(À )menthol, [64] benzenesulfonamide, [65] pyridine [66] and azo compounds. [67] Microwaves have been also employed to synthesize silicon [68] lanthanide(III), [69] lead, [49,70] and platinum [71] derivatives, and phthalocyanine-based polymers.…”

Section: Microwave Irradiationmentioning

confidence: 99%

Phthalocyanines Synthesis: A State‐of‐The‐Art Review of Sustainable Approaches Through Green Chemistry Metrics

Zanotti,

Palmeri,

Raglione

2024

Chemistry A European J

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Driven by escalating environmental concerns, synthetic chemistry faces an urgent need for a green revolution. Green chemistry, with its focus on low environmental impacting chemicals and minimized waste production, emerges as a powerful tool in addressing this challenge. Metrics such as the E‐factor guide the design of environmentally friendly strategies for chemical processes by quantifying the waste generated in obtaining target products, thus enabling interventions to minimize it. Phthalocyanines (Pcs), versatile molecules with exceptional physical and chemical properties, hold immense potential for technological applications. This review aims to bridge the gap between green chemistry and phthalocyanine synthesis by collecting the main examples of environmentally sustainable syntheses documented in the literature. The calculation of the E‐factor of a selection of them provides insights on how crucial it is to evaluate a synthetic process in its entirety. This approach allows for a better evaluation of the actual sustainability of the phthalocyanine synthetic process and indicates possible strategies to improve it.

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Tetraiodophthalocyanines: Simple and convenient synthetic protocol and structural modification via Sonogashira cross-coupling reaction

Cited by 5 publications

References 71 publications

Coupling of Phthalocyanines with Plasmonic Gold Nanoparticles by Click Chemistry for an Enhanced Singlet Oxygen Based Photoelectrochemical Sensing

Coupling of Phthalocyanines with Plasmonic Gold Nanoparticles by Click Chemistry for an Enhanced Singlet Oxygen Based Photoelectrochemical Sensing

Coupling of phthalocyanines with plasmonic gold nanoparticles by click chemistry for an enhanced singlet oxygen based photoelectrochemical sensing

Phthalocyanines Synthesis: A State‐of‐The‐Art Review of Sustainable Approaches Through Green Chemistry Metrics

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