Synthesis, characterization and investigation of the photophysical and photochemical properties of highly soluble novel metal-free, zinc(<scp>ii</scp>), and indium(<scp>iii</scp>) phthalocyanines substituted with 2,3,6-trimethylphenoxy moieties

Gürel, Ekrem; Pişkin, Mehmet; Altun, Selçuk; Odabaş, Zafer; Durmuş, Mahmut

doi:10.1039/c5dt00304k

Cited by 51 publications

(11 citation statements)

References 40 publications

(42 reference statements)

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“…The peak can be protonation of the nitrogen atoms on the Pc core instead of J type aggregation because chloroform contains a little amounts of acidic impurities (generally HCl) (Gürel et al 2015, Gürel et al 2016. Moreover, the absorption intensity of this extra peak increased by adding trifluoroacetic acid and decreased by adding potassium carbonate (Figure 8 for 3 in chloroform) as in the literature (Gürel et al 2015, Gürel et al 2016. This obtained result substantiated the protonation…”

Section: Aggregation Studiessupporting

confidence: 76%

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Pişkin¹,

Odabaş²

2016

KSEJ

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They have found wide application in technological areas such fluorescence materials (Buono-Core et al. 1990, Wu et al. 2008), electroluminescence (Edward et al. 1997), and as fluorescence probes and labels in a variety of biological systems (Meares et al. 1984, Kukhta et al. 2006, Wu and Zhang 2002). Lutetium phthalocyanine complexes of (LuPcs) have been studied owing to their rich electrochromic and gas-sensing properties and high intrinsic conductivity (Nicholson et al. 1993, Zugle et al. 2011, Weiss and Fischer 2003, Besbes et al. 1987, Petty 1992). Their properties can be tuned by depending on the substituents at peripheral or non-peripheral positions onto the macrocycle ring (Yılmaz et al. 2003). Therefore, it is important to know electrochemical and spectroelectrochemical properties of these complexes to be used in various technological applications. Moreover, solubilities of phthalocyanines, which play key role for their application areas, can be enhanced substi

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Section: Aggregation Studiessupporting

confidence: 76%

Untitled

Pişkin¹,

Odabaş²

2016

KSEJ

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“…) show their monomeric behavior as evidenced by a narrow, single Q‐band at 682 and 695 nm, for complexes 2 and 3 , respectively (Table ), which is typical for metalated phthalocyanines with degenerate D 4h symmetry . The red shift in the Q‐band of complex 3 compared to 2 can be attributed to the nonplanar effect of the indium(III) ion, with a relatively bigger atomic radius than the zinc(II) as the central metal ion in the Pc cavity .…”

Section: Resultsmentioning

confidence: 99%

Improved Photophysical and Photochemical Properties of Thiopheneethoxy Substituted Metallophthalocyanines on Immobilization onto Gold‐speckled Silica Nanoparticles

Dube

Oluwole

Nyokong

2018

Photochem & Photobiology

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This work reports on the synthesis of tetrakis-[(thiophineethoxy) phthalocyaninato] indium(II) chloride (3). The photophysical behavior of complex 3 was compared to that of the Zn derivative (tetrakis-[(thiophineethoxy) phthalocyaninato] zinc(II) (complex 2)). The compounds were interacted with gold-speckled silica (GSS) nanoparticles via Au-S self assembly to afford the conjugates (2-GSS and 3-GSS). The photophysicochemical behavior of the compounds and their conjugates were assessed. The conjugates afforded a decrease in fluorescence quantum yields and lifetimes with improved triplet and singlet oxygen quantum yields in comparison with complexes 2 and 3 alone. The complexes and their conjugates could serve as good candidates for photodynamic therapy.

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“…In this study, the aggregation behavior of the phthalocyanine complexes (3-6) were investigated in various commonly known organic solvents DMSO, DMF, THF, toluene, the Q bands highly shift to the red region of the spectra (Kobayashi et al 2003, Gürel et al 2015. The Q bands of the alpha-substituted phthalocyanines (3 and 5) were red-shifted when compared to the beta-counterparts (4 and 6) in DMSO (Fig 3a and 3b).…”

Section: Aggregation Studiesmentioning

confidence: 86%

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Pişkin¹,

Öztürk²,

Odabaş³

2017

KSEJ

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This work presents the synthesis and characterization of non-aggregated and highly soluble copper(II) and tin(II) phthalocyanines substituted with 2,6-dimethoxyphenoxy groups at the non-peripheral (alpha) and peripheral (beta) positions. The phthalocyanines have been characterized by common spectroscopic techniques. They show excellent solubility and non-aggregated species in common organic solvents such as dimethylsulfoxide, dimethylformamide, tetrahydrofuran, toluene, acetonitrile, chloroform and dichloromethane, which make them candidates to use for many applications in different fields of science and technology. The effects positions of substituent on the phthalocyanine skeleton and the variety of central metal ions on the phthalocyanine of aggregation and on their spectroscopic properties were determined in different solvents as mentioned above. The novel synthesized copper phthalocyanines were not evaluated for fluorescence, photophysical and photochemical properties due to transition metal and paramagnetic behavior of central metal in the phthalocyanine cavity. The effects of substituent and their positions on the tin(II) phthalocyanines' on their photophysical (fluorescence quantum yields and lifetimes) and photochemical properties (singlet oxygen generation and photodegradation under light irradiation) were also investigated and reported in dimethylsulfoxide for the first time.

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Synthesis, characterization and investigation of the photophysical and photochemical properties of highly soluble novel metal-free, zinc(ii), and indium(iii) phthalocyanines substituted with 2,3,6-trimethylphenoxy moieties

Cited by 51 publications

References 40 publications

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Improved Photophysical and Photochemical Properties of Thiopheneethoxy Substituted Metallophthalocyanines on Immobilization onto Gold‐speckled Silica Nanoparticles

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