Novel porphyrazines containing peripherally functionalized macrocyclic (N2O2, N2S2) units: Synthesis and characterization

Bílgín, Ahmet; Ertem, Beytullah; Gök, Yaşar

doi:10.1016/j.dyepig.2008.07.002

Cited by 14 publications

(13 citation statements)

References 42 publications

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“…The dyes exhibit an array of molecular structural varieties, each imparting unique physiochemical and photophysical profiles. These characteristics further highlight their potential for application in specific medical, scientific and industrial niches (described by Bilgin et al …”

Section: Macrocycle Dyesmentioning

confidence: 86%

“…Here, nitrogen electrons are no longer available to the macrocycle π‐system resulting in a degenerate LUMO and LUMO + 1π* (when two or more MO exhibit equal e − energies) and nearly degenerate HOMO and HOMO‐1π. Single Q‐band peaks can then observed . With regard to symmetry, such observations can be further influenced by the presence of non‐symmetrical core‐bound axial satellites (small charged functional groups bound to a core metal bearing additional charges not utilized by the macrocycle ring).…”

Section: Macrocycle Dyesmentioning

confidence: 99%

“…In comparison with other porphyrin derivatives, porphyrazines have been less researched due to synthesis and purification difficulties . However, they have recently gained interest for light‐based applications for diagnoses and therapies.…”

Section: Considerations For Light Sources and Photosensitizers In Phomentioning

confidence: 99%

“…Therefore, syntheses of unsymmetrical porphyrazines with diverse peripheral substituents allow for improved properties, but require the use of multiple precursors and more complicated methods of purification . Additionally, both core and peripheral metal complexing have also been linked to the nature of Pz solubility and phototoxicity …”

Section: Considerations For Light Sources and Photosensitizers In Phomentioning

confidence: 99%

“…Phthalocyanines are popularly co‐ordinated to a range of metal ions including Ld(II), Ni(II), Pd(II), Cu(II), Ga(II), Ge(II), Co(II) and Fe(II); however, Al(II), Zn(II), Sn(IV) and Si(II) derivatives are the most extensively studied to date Likewise, texaphyrins are also closely associated with numerous metal complexes including Cd(II), Mg(II), Mn(II), Ci(II), Ni(II), Zn(II), Fe(II), Sm(II), Gd(III), La(III), Lu(III), Er(III), Y(III) and In(III) . Porphyrazine co‐ordination with Zn(II), Co(II), Ni(II), Pd(II), Gd(III), Mg(II) and Cu(II) has also been detailed . Conversely, research associating metal ions to the large class of chlorin‐based Ps for PDT are not common with the few reported studies including benzoporphyrins complexed to In(III), Pd(II) and Pt(II), bacteriochlorins complexed to Cu(II), Zn(II), Pd(II), NI(II), Cd(II), In(III) and Sn(II) and porphycenes complexed to Al(III) and Co(II) …”

Section: Shortcomings Of Current Photosensitizers For Phototherapymentioning

confidence: 99%

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Mechanistics and photo‐energetics of macrocycles and photodynamic therapy: An overview of aspects to consider for research

Horne

Cronjé

2017

Chem Biol Drug Des

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Research within the field of photodynamic therapy has escalated over the past 20 years. The required conjunctional use of photosensitizers, particularly of the macrocycle structure, has lead to a vast repertoire of derivatives that branch classes and subclasses thereof. Each exhibits a differential range of physiochemical properties that influence their potential applications within the larger phototherapy field for use in either diagnostics, photodynamic therapy, both or none. Herein, we provide an overview of these properties as they relate to photodynamic therapy and to a lesser extent diagnostics. By summarizing the mechanistics of photodynamic therapy coupled to the photo-energetics displayed by macrocycle photosensitizers, we aimed to highlight the critical aspects any researcher should be aware of and consider when selecting and performing research for therapeutic application purposes. These include photosensitizer, photophysical and structural properties, synthesis design and subsequent attributes, main applications within research, common shortcomings exhibited and the current methods practiced to overcome them. K E Y W O R D Sco

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Section: Macrocycle Dyesmentioning

confidence: 86%

Section: Macrocycle Dyesmentioning

confidence: 99%

Section: Considerations For Light Sources and Photosensitizers In Phomentioning

confidence: 99%

Section: Considerations For Light Sources and Photosensitizers In Phomentioning

confidence: 99%

Section: Shortcomings Of Current Photosensitizers For Phototherapymentioning

confidence: 99%

See 3 more Smart Citations

Mechanistics and photo‐energetics of macrocycles and photodynamic therapy: An overview of aspects to consider for research

Horne

Cronjé

2017

Chem Biol Drug Des

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Experimental and computational study on the reactivity of 2,3-bis[(3-pyridylmethyl)amino]-2(Z)-butene-1,4-dinitrile, a key intermediate for the synthesis of tribenzoporphyrazine bearing peripheral methyl(3-pyridylmethyl)amino substituents

et al. 2011

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An earlier developed alkylating path leading to tetraalkylated diaminomaleonitrile derivatives was explored. Attempts to explain the reactivity of the representative dialkylated diaminomaleonitrile 2,3-bis[(3-pyridylmethyl)amino]-2(Z)-butene-1,4-dinitrile during the alkylation reaction were performed using X-ray and density functional theory (DFT) studies. The condensed Fukui functions accompanied by softness indices were found to be useful in explaining its reactivity observed during the reaction. The values of the Fukui functions and condensed softness for electrophilic attack calculated from Mulliken, Löwdin, and natural population analyses closely corresponded to the experimental observations. When 2,3-bis[(3-pyridylmethyl)amino]-2(Z)-butene-1,4-dinitrile disodium salt was treated with dimethyl sulfate at lower temperatures the alkylation reaction prevailed, whereas at higher temperatures the alkylating agent acted as a hydride anion acceptor, which favored the elimination reaction. The tetraalkylated dinitrile 2,3-bis[methyl(3-pyridylmethyl)amino]-2(Z)-butene-1,4-dinitrile was used in the synthesis of tribenzoporphyrazine bearing methyl(3-pyridylmethyl)amino groups, which was subsequently subjected to solvatochromic and metallation studies. The changes observed during metallation seem to result from the coordination of the 3-pyridyl group by a palladium ion. This could influence the configuration of the methyl(3-pyridylmethyl)amino moiety, causing more effective donation of a lone pair of electrons from peripheral nitrogen to the macrocyclic ring.Graphical abstract.Electronic supplementary materialThe online version of this article (doi:10.1007/s00706-011-0503-9) contains supplementary material, which is available to authorized users.

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New diaminomaleonitrile-based azo-azomethine dyes; synthesis, characterization and spectral properties

Khanmohammadi

Abdollahi

2012

Dyes and Pigments

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Novel porphyrazines containing peripherally functionalized macrocyclic (N2O2, N2S2) units: Synthesis and characterization

Cited by 14 publications

References 42 publications

Mechanistics and photo‐energetics of macrocycles and photodynamic therapy: An overview of aspects to consider for research

Mechanistics and photo‐energetics of macrocycles and photodynamic therapy: An overview of aspects to consider for research

Experimental and computational study on the reactivity of 2,3-bis[(3-pyridylmethyl)amino]-2(Z)-butene-1,4-dinitrile, a key intermediate for the synthesis of tribenzoporphyrazine bearing peripheral methyl(3-pyridylmethyl)amino substituents

New diaminomaleonitrile-based azo-azomethine dyes; synthesis, characterization and spectral properties

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