Synthesis and photochemical characterization of a zinc phthalocyanine–zinc porphyrin heterotrimer and heterononamer

Zhao, Zhixin; Nyokong, Tebello; Maree, M. David

doi:10.1039/b508478d

Cited by 32 publications

(21 citation statements)

References 21 publications

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“…Moreover, the rate of energy transfer strongly depends on mutual orientation of transition dipole moments and distance between interacting chromophores. Besides dyads the synthesis and some photophysical properties of few phthalocyanine-porphyrin molecular systems containing up to eight porphyrin chromophores was described [32][33][34].…”

Section: Introductionmentioning

confidence: 99%

Photoinduced electron and energy transfer in a new porphyrin–phthalocyanine triad

et al. 2006

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Section: Introductionmentioning

confidence: 99%

Photoinduced electron and energy transfer in a new porphyrin–phthalocyanine triad

et al. 2006

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“…The fluorescence quantum yield (F F ) values for ClInTPP, 2a, 2b and the 2a-AuNPs nanoconjugate were determined in DMSO using a comparative method described previously in the literature [36]. Zinc(II) meso-substituted tetraphenylporphyrin (ZnTPP) was used as the standard (F F = 0.0397) [36].…”

Section: Fluorescence and Singlet Oxygen Quantum Yieldsmentioning

confidence: 99%

Photophysicochemical properties and photodynamic therapy activity of chloroindium(III) tetraarylporphyrins and their gold nanoparticle conjugates

Soy

Babu

Oluwole

et al. 2019

J. Porphyrins Phthalocyanines

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Novel chloroindium(III) complexes of tetra(4-methylthiophenyl)porphyrin (2a) and tetra-2-thienylporphyrin (2b) dyes have been synthesized and characterized. The main goal of the project was to identify fully symmetric porphyrin dyes with Q-band regions that lie partially in the therapeutic window that are suitable for use in photodynamic therapy (PDT). 2a and 2b were found to have fluorescence quantum yield values [Formula: see text] 0.01 and moderately high singlet oxygen quantum yields (0.54−0.73) due to heavy atom effects associated with the sulfur and indium atoms. The dark toxicity and PDT activity against epithelial breast cancer cells (MCF-7) were investigated over a dose range of 3.0−40 [Formula: see text]g [Formula: see text] mL[Formula: see text]. The in vitro dark cytotoxicity of 2a is significantly lower than that of 2b at [Formula: see text] 40 [Formula: see text]g [Formula: see text] mL[Formula: see text]. 2a was conjugated with gold nanoparticles (AuNPs) to form a nanoconjugate (2a-AuNPs), which exhibited a higher singlet oxygen quantum yield ([Formula: see text] value and PDT activity than was observed for 2a alone. The results suggest that the AuNPs nanoconjugates of readily synthesized fully symmetric porphyrin dyes are potentially suitable for PDT applications, if meso-aryl substituents that provide scope for nanoparticle conjugation can be introduced that shift the Q bands into the therapeutic window.

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“…[34] Bis(porphyrin)-phthalocyanine triad was synthesized according to literature methods with few modifications. [26] Synthesis of (ZnP-ZnP) 2 -ZnPc triad 5-(4-Hydroxyphenyl)-10, 15,20-tris(tolualyl)porphyrin (1) 4-Hydroxybenzaldehyde (500 mg, 4.09 mmol), p-tolualdehyde (1.44 mL, 12.28 mmol), and pyrrole (1.14 mL, 16.36 mmol) were kept in a round-bottom (RB) flask (500 mL), and then heated at reflux with 100 mL of propionic acid for 4 h. After cooling the mixture to RT, the solvent was evaporated, and mixture was purified by using silica column. The desired compound was eluted by CHCl 3 /CH 3 OH (90:10) as a second fraction.…”

Section: Chemicalsmentioning

confidence: 99%

Supramolecular Tetrad Featuring Covalently Linked Bis(porphyrin)–Phthalocyanine Coordinated to Fullerene: Construction and Photochemical Studies

Lim

Karr

et al. 2014

Chemistry A European J

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A multimodular donor-acceptor tetrad featuring a bis(zinc porphyrin)-(zinc phthalocyanine) ((ZnP-ZnP)-ZnPc) triad and bis-pyridine-functionalized fullerene was assembled by a "two-point" binding strategy, and investigated as a charge-separating photosynthetic antenna-reaction center mimic. The spectral and computational studies suggested that the mode of binding of the bis-pyridine-functionalized fullerene involves either one of the zinc porphyrin and zinc phthalocyanine (Pc) entities of the triad or both zinc porphyrin entities leaving ZnPc unbound. The binding constant evaluated by constructing a Benesi-Hildebrand plot by using the optical data was found to be 1.17×10(5) M(-1), whereas a plot of "mole-ratio" method revealed a 1:1 stoichiometry for the supramolecular tetrad. The mode of binding was further supported by differential pulse voltammetry studies, in which redox modulation of both zinc porphyrin and zinc phthalocyanine entities was observed. The geometry of the tetrad was deduced by B3LYP/6-31G* optimization, whereas the energy levels for different photochemical events was established by using data from the optical absorption and emission, and electrochemical studies. Excitation of the zinc porphyrin entity of the triad and tetrad revealed ultrafast singlet-singlet energy transfer to the appended zinc phthalocyanine. The estimated rate of energy transfer (k(ENT)) in the case of the triad was found to be 7.5×10(11) s(-1) in toluene and 6.3×10(11) s(-1) in o-dichlorobenzene, respectively. As was predicted from the energy levels, photoinduced electron transfer from the energy-transfer product, that is, singlet-excited zinc phthalocyanine to fullerene was verified from the femtosecond-transient spectral studies, both in o-dichlorobenzene and toluene. Transient bands corresponding to ZnPc(⋅+) in the 850 nm range and C60(⋅-) in the 1020 nm range were clearly observed. The rate of charge separation, k(CS), and rate of charge recombination, k(CR), for the (ZnP-ZnP)-ZnPc(⋅+):Py2C60(⋅-) radical ion pair (from the time profile of 849 nm peak) were found to be 2.20×10(11) and 6.10×10(8) s(-1) in toluene, and 6.82×10(11) and 1.20×10(9) s(-1) in o-dichlorobenzene, respectively. These results revealed efficient energy transfer followed by charge separation in the newly assembled supramolecular tetrad.

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Synthesis and photochemical characterization of a zinc phthalocyanine–zinc porphyrin heterotrimer and heterononamer

Cited by 32 publications

References 21 publications

Photoinduced electron and energy transfer in a new porphyrin–phthalocyanine triad

Photoinduced electron and energy transfer in a new porphyrin–phthalocyanine triad

Photophysicochemical properties and photodynamic therapy activity of chloroindium(III) tetraarylporphyrins and their gold nanoparticle conjugates

Supramolecular Tetrad Featuring Covalently Linked Bis(porphyrin)–Phthalocyanine Coordinated to Fullerene: Construction and Photochemical Studies

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