The synthesis and fluorescence behaviour of phthalocyanines unsymmetrically substituted with naphthol and carboxy groups
- Authors: Nombona, Nolwazi , Antunes, Edith M , Nyokong, Tebello
- Date: 2010
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/261534 , vital:53418 , xlink:href="https://doi.org/10.1016/j.dyepig.2009.11.010"
- Description: Unsymmetrically substituted phthalocyanines 8,15,22-tris-(naphtho)-2-(carboxy)phthalocyanine, [8,15,22-tris-(naphtho)-2-(carboxy)phthalocyanato]zinc(II), 8,15,22-tris-(naphtho)-4,5-(3-carboxy-1,2-dioxyphenyl)phthalocyanine and [8,15,22-tris-(naphtho)-4,5-(3-carboxy-1,2-dioxyphenoxy)phthalocyanato]zinc(II) were prepared using the mixed phthalonitrile cyclotetramerization of 3-(1-naphthoxy) phthalonitrile with a carboxylic acid phthalonitrile. The phthalocyanines were separated using column chromatography employing a mixture of THF, ammonia and water. The novel compounds were characterized using UV–Vis, IR, 1H NMR and mass spectrometry as well as elemental analysis. Fluorescence quantum yields were found to range from 0.05 to 0.16.
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- Date Issued: 2010
The synthesis and photophysical properties of novel cationic tetra pyridiloxy substituted aluminium, silicon and titanium phthalocyanines in water
- Authors: Masilela, Nkosiphile , Nyokong, Tebello
- Date: 2010
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/249159 , vital:51783 , xlink:href="https://doi.org/10.1016/j.jlumin.2010.04.011"
- Description: This work reports on the synthesis, characterisation and photophysical properties of new unquaternized β-2,(3)-tetra-(2 pyridiloxy) aluminium(III) (3a), silicon(IV) (3b), titanium(IV) (3c) phthalocyanines and their water-soluble quaternized counterparts, 4a, 4b and 4c, respectively. The water-soluble silicon(IV) (4b) and titanium(IV) (4c) phthalocyanine derivatives were found to be aggregated in aqueous media but were partially or fully disaggregated in the presence of a surfactant Cremophor® EL (CEL). The photophysical properties of aggregated complexes were investigated both in the presence of CEL and in pH 11 alone. Low triplet and fluorescence yield were obtained in pH 11 but an improvement was achieved upon addition of CEL for the aggregated complexes. The unquaternized silicon(IV) phthalocyanine complex (3b) gave the highest triplet quantum yield of 0.77 in DMF followed by its quaternized derivative (4b) with triplet yield of 0.73 in pH 11 plus CEL. The highest triplet lifetime of 220 μs was obtained for 4b in the presence of CEL. Higher fluorescence yields of 0.23 were obtained for quaternized water-soluble aluminium(III) phthalocyanine derivative (4a) in the presence of CEL.
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- Date Issued: 2010
Tuning the physico-electrochemical properties of novel cobalt (II) octa [(3, 5-biscarboxylate)-phenoxy] phthalocyanine complex using phenylamine-functionalised SWCNTs
- Authors: Agboola, Bolade O , Ozoemena, Kenneth I , Nyokong, Tebello , Fukuda, Takamitsu , Kobayashi, Nagao
- Date: 2010
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/261692 , vital:53435 , xlink:href="https://doi.org/10.1016/j.carbon.2009.10.023"
- Description: The integration of phenylamine-functionalised SWCNTs (SWCNT-phenylamine) with a novel cobalt (II) octa[(3,5-biscarboxylate)-phenoxy] phthalocyanine (CoOBPPc) complex has been described. The physical and electrochemical properties of the CoOBPPc-SWCNT-phenylamine hybrid were evaluated using spectroscopy (IR and UV–vis), field emission scanning electron microscopy and electrochemistry (cyclic voltammetry and electrochemical impedance spectroscopy). Integration of SWCNT-phenylamine resulted in the physical transformation of the CoOBCPPc from the usually bluish colour of cobalt phthalocyanine complexes to a beautiful bright green colour. In addition, the heterogeneous electron transfer kinetics and electrocatalytic properties of the CoOBCPPc were greatly enhanced following the attachment of the SWCNT-phenylamine. The potential electrocatalytic application of the hybrid was tested using β-nicotinamide adenine dinucleotide (NADH) as a model biological analyte. Interestingly, the onset oxidation potential of this analyte was significantly reduced (300 mV) by this hybrid compared to the bare electrode.
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- Date Issued: 2010
Characterization of amine-functionalized single-walled carbon nanotube-low symmetry phthalocyanine conjugates
- Authors: Chidawanyika, Wadzanai J U , Nyokong, Tebello
- Language: English
- Type: Article
- Identifier: vital:7237 , http://hdl.handle.net/10962/d1019688
- Description: Functionalization of single-walled carbon nanotubes (SWCNTs) with amine groups using a previously developed diazonium approach, followed by reaction with a carboxylic acid moiety allows direct attachment by an amide bond. We have developed a new SWCNT-low symmetry phthalocyanine conjugate using this approach, using dicyclohexylcarbodiimide as an activating agent to facilitate formation of an amide bond to give a covalently linked conjugate. A conjugate formed by non-covalent attachment has been used for a comparative investigation by FT-IR, Raman, and UV–Vis spectroscopies, and thermal gravimetric analysis. The fluorescence of the phthalocyanine is quenched in the conjugate. , Original publication is available at http://dx.doi.org/10.1016/j.carbon.2010.04.015
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Novel, soluble, FluXoro functional substituted zinc phthalocyanines; synthesis, characterization and photophysicochemical properties
- Authors: Erdoğmuş, Ali , Nyokong, Tebello
- Language: English
- Type: Article
- Identifier: vital:7235 , http://hdl.handle.net/10962/d1019686
- Description: Three novel phthalonitriles and the respective, peripheral tetrakis zinc phthalocyanines were synthesized and characterized using elemental analysis, IR, 1H NMR, mass spectra and electronic spectroscopy. The phthalocyanines displayed good solubility in organic solvents such as CHCl3, DCM, DMSO, DMF, THF and toluene. The presence of a long chain fluorine substitituent was found to result in reduced aggregation. The singlet oxygen, photodegradation, fluorescence quantum yield, triplet quantum yield and triplet life time of the complexes in toluene were determined. The effect of fluoro-functional groups on the photophysical and photochemical parameters of the zinc(II) phthalocyanines are also reported. Fluorescence quantum yields for the complexes ranged from 0.021 to 0.041 , Original publication is available at http://dx.doi.org/10.1016/j.dyepig.2010.01.001
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Synthesis and electrochemical properties of new cobalt and manganese phthalocyanine complexes tetra-substituted with 3,4-(methylendioxy)-phenoxy
- Authors: Erdoğmuş, Ali , Akinbulu, Isaac Adebayo , Nyokong, Tebello
- Language: English
- Type: Article
- Identifier: vital:7234 , http://hdl.handle.net/10962/d1019672
- Description: The synthesis and electrochemical properties of new cobalt and manganese phthalocyanine complexes, tetra-substituted with 3,4-(methylendioxy)-phenoxy at the peripheral (complexes 3 and 5) and non-peripheral (complexes 4 and 6) positions, are reported. Complexes 3 and 4 showed Q-band absorption, in DMF, at 668 and 686 nm, respectively while Q-band due to complexes 5 and 6 appeared at 732 and 760 nm, respectively in CHCl3. All the complexes showed well resolved redox processes attributed to both metal and ring based processes. Complexes 3 and 4 showed four redox processes, labeled I, II, III and IV. For complex 3, process I (CoIPc−2/CoIPc−3) was observed at −1.45 V, II (CoIIPc−2/CoIPc−2) at −0.38 V, III (CoIIIPc−2/CoIIPc−2) at +0.49 V and IV (CoIIIPc−1/CoIIIPc−2) at +0.97 V versus Ag|AgCl. Similar processes were observed for complex 4 at −1.36 V, −0.27 V, +0.56 V, +1.03 V versus Ag|AgCl, respectively. Complexes 5 and 6 showed two redox processes (I and II). For complex 5, these processes appeared at −0.79 V (MnIIPc−2/MnIIPc−3, I) and −0.07 V versus Ag|AgCl (MnIIIPc−2/MnIIPc−2, II), while for complex 6, they were observed at −0.86 V and −0.04 V versus Ag|AgCl. Spectroelectrochemistry was used to probe and confirm the origin of these processes. , Original publication is availabe at http://dx.doi.org/10.1016/j.poly.2010.05.012
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Synthesis of zinc phthalocyanine derivatives with improved photophysicochemical properties in aqueous media
- Authors: Erdoğmuş, Ali , Nyokong, Tebello
- Language: English
- Type: Article
- Identifier: vital:7236 , http://hdl.handle.net/10962/d1019687
- Description: The synthesis, photophysical and photochemical properties of new peripherally (β) tetra-substituted thioquinoline Zn(II) (2) and quaternized thioquinoline Zn(II) phthalocyanines (3) and quaternized fluoro functional thiopyridine Zn(II) (5) are described for the first time. These complexes (2, 3 and 5) have been synthesized and characterized by elemental analysis, IR, 1H NMR spectroscopy and electronic spectroscopy. Complexes 2, 4 and 6have good solubility in organic solvents such as CHCl3, DCM, DMSO, DMF, THF and toluene and are not aggregated in all solvents (except for 2 in DMSO) within a wide concentration range. Complexes 3 and 5 showed very good solubility in water as well as DMSO and DMF. General trends are described for singlet oxygen, photodegradation, fluorescence quantum yields, triplet quantum yields and triplet life times of these complexes in DMSO (2, 4 and 6) and water (3 and 5). Complex 3 gave a very large triplet quantum yield in aqueous media (ΦT = 0.8 in water plus Triton X-100) and a reasonable triplet lifetime of 110 μs. Photophysical and photochemical properties of the phthalocyanines complexes 2–6 are very useful for PDT. , Original publication is available at http://dx.doi.org/10.1016/j.molstruc.2010.04.048
- Full Text: false
Synthetic pathways to water-soluble phthalocyanines and close analogs
- Authors: Dumoulin, Fabienne , Durmus, Mahmut , Ahsen, Vefa , Nyokong, Tebello
- Language: English
- Type: Article
- Identifier: vital:7240 , http://hdl.handle.net/10962/d1019720
- Description: The different types of water-soluble phthalocyanines are presented and their synthesis is reviewed. , Original publication is available at http://dx.doi.org/10.1016/j.ccr.2010.05.002
- Full Text: false
Tuning the physico-electrochemical properties of novel cobalt (II) octa[(3,5-biscarboxylate)-phenoxy] phthalocyanine complex using phenylamine-functionalised SWCNTs
- Authors: Agboola, Bolade Oyeyinka , Ozoemena, Kenneth I. , Nyokong, Tebello , Fukuda, Takamitsu , Kobayashi, Nagao
- Language: English
- Type: Article
- Identifier: vital:7238 , http://hdl.handle.net/10962/d1019689
- Description: The integration of phenylamine-functionalised SWCNTs (SWCNT-phenylamine) with a novel cobalt (II) octa[(3,5-biscarboxylate)-phenoxy] phthalocyanine (CoOBPPc) complex has been described. The physical and electrochemical properties of the CoOBPPc-SWCNT-phenylamine hybrid were evaluated using spectroscopy (IR and UV–vis), field emission scanning electron microscopy and electrochemistry (cyclic voltammetry and electrochemical impedance spectroscopy). Integration of SWCNT-phenylamine resulted in the physical transformation of the CoOBCPPc from the usually bluish colour of cobalt phthalocyanine complexes to a beautiful bright green colour. In addition, the heterogeneous electron transfer kinetics and electrocatalytic properties of the CoOBCPPc were greatly enhanced following the attachment of the SWCNT-phenylamine. The potential electrocatalytic application of the hybrid was tested using β-nicotinamide adenine dinucleotide (NADH) as a model biological analyte. Interestingly, the onset oxidation potential of this analyte was significantly reduced (300 mV) by this hybrid compared to the bare electrode. , Original publication is available at http://dx.doi.org/doi:10.1016/j.carbon.2009.10.023
- Full Text: false