Regioisomers of magnesium(II) phthalocyanine bearing menthol substituents - Synthesis, spectral, electrochemical and computational studies

Szymczak, Joanna; Rębiś, Tomasz; Kotkowiak, Michał; Wicher, Barbara; Sobotta, Łukasz; Tykarska, Ewa; Mielcarek, Jadwiga; Kryjewski, Michał

doi:10.1016/j.dyepig.2021.109357

Cited by 7 publications

(3 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This distribution of emission maxima may be associated with the presence of regioisomers of Pc1 as discussed in Section . In a similar manner, the isolated regioisomers of tetra-α- substituted Mg-phthalocyanines were reported to exhibit slightly different fluorescence emission maxima . The linear correlation between fluorescence intensity and concentration in the investigated range (Figure S4A) underlines the presence of monomers as emitting species in DMSO.…”

Section: Resultsmentioning

confidence: 97%

“…In a similar manner, the isolated regioisomers of tetra-αsubstituted Mg-phthalocyanines were reported to exhibit slightly different fluorescence emission maxima. 48 The linear correlation between fluorescence intensity and concentration in the investigated range (Figure S4A) underlines the presence of monomers as emitting species in DMSO. On the other hand, for Pc1-PBS, the fluorescence emission remains constant between 0.25 and 1 μM (Figure S4B).…”

Section: Behavior Of Pc1 In Aqueous Pbs Solutionmentioning

confidence: 95%

See 1 more Smart Citation

Comparing PVP and Polymeric Micellar Formulations of a PEGylated Photosensitizing Phthalocyanine by NMR and Optical Techniques

et al. 2023

View full text Add to dashboard Cite

Phthalocyanines are ideal candidates as photosensitizers for photodynamic therapy (PDT) of cancer due to their favorable chemical and photophysical properties. However, their tendency to form aggregates in water reduces PDT efficacy and poses challenges in obtaining efficient forms of phthalocyanines for therapeutic applications. In the current work, polyvinylpyrrolidone (PVP) and micellar formulations were compared for encapsulating and monomerizing a water-soluble zinc phthalocyanine bearing four non-peripheral triethylene glycol chains (Pc1). 1H NMR spectroscopy combined with UV–vis absorption and fluorescence spectroscopy revealed that Pc1 exists as a mixture of regioisomers in monomeric form in dimethyl sulfoxide but forms dimers in an aqueous buffer. PVP, polyethylene glycol castor oil (Kolliphor RH40), and three different triblock copolymers with varying proportions of polyethylene and polypropylene glycol units (termed P188, P84, and F127) were tested as micellar carriers for Pc1. 1H NMR chemical shift analysis, diffusion-ordered spectroscopy, and 2D nuclear Overhauser enhancement spectroscopy was applied to monitor the encapsulation and localization of Pc1 at the polymer interface. Kolliphor RH40 and F127 micelles exhibited the highest affinity for encapsulating Pc1 in the micellar core and resulted in intense Pc1 fluorescence emission as well as efficient singlet oxygen formation along with PVP. Among the triblock copolymers, efficiency in binding and dimer dissolution decreased in the order F127 > P84 > P188. PVP was a strong binder for Pc1. However, Pc1 molecules are rather surface-attached and exist as monomer and dimer mixtures. The results demonstrate that NMR combined with optical spectroscopy offer powerful tools to assess parameters like drug binding, localization sites, and dynamic properties that play key roles in achieving high host–guest compatibility. With the corresponding adjustments, polymeric micelles can offer simple and easily accessible drug delivery systems optimizing phthalocyanines’ properties as efficient photosensitizers.

show abstract

Section: Resultsmentioning

confidence: 97%

Section: Behavior Of Pc1 In Aqueous Pbs Solutionmentioning

confidence: 95%

Comparing PVP and Polymeric Micellar Formulations of a PEGylated Photosensitizing Phthalocyanine by NMR and Optical Techniques

et al. 2023

View full text Add to dashboard Cite

show abstract

“…An important advantage of phthalocyanines is the ability to vary their structure widely by replacing the central metal and substituents, both in the aromatic macrocycle and in axial positions. Such modification leads to a significant change in the solubility of phthalocyanine derivatives, as well as their optical, electrophysical, and catalytic properties [8][9][10][11][12]. For example, the introduction of fluorine substituents into the phthalocyanine ring leads to a decrease in their solubility in conventional organic solvents, but fluorinated phthalocyanines become capable of transferring into the gaseous phase without decomposition in a vacuum [13,14], which makes it possible to obtain their homogeneous thin films using a physical vapor deposition method.…”

Section: Introductionmentioning

confidence: 99%

Octafluoro-Substituted Phthalocyanines of Zinc, Cobalt, and Vanadyl: Single Crystal Structure, Spectral Study and Oriented Thin Films

Sukhikh

Klyamer

Bonegardt

et al. 2023

IJMS

View full text Add to dashboard Cite

In this work, octafluoro-substituted phthalocyanines of zinc, vanadyl, and cobalt (MPcF8, M = Zn(II), Co(II), VO) were synthesized and studied. The structures of single crystals of the obtained phthalocyanines were determined. To visualize and compare intermolecular contacts in MPcF8, an analysis of Hirshfeld surfaces (HS) was performed. MPcF8 nanoscale thickness films were deposited by organic molecular beam deposition technique and their structure and orientation were studied using X-ray diffraction. Comparison of X-ray diffraction patterns of thin films with the calculated diffractograms showed that all three films consisted of a single crystal phase, which corresponded to a phase of single crystals. Only one strong diffraction peak corresponding to the plane (001) was observed on the diffraction pattern of each film, which indicated a strong preferred orientation with the vast majority of crystallites oriented with a (001) crystallographic plane parallel to the substrate surface. The effect of the central metals on the electronic absorption and vibrational spectra of the studied phthalocyanines as well as on the electrical conductivity of their films is also discussed.

show abstract

Phthalocyanines as corrosion inhibitors

Nnaji¹,

Soy²,

Ikala³

et al. 2023

Smart Anticorrosive Materials

View full text Add to dashboard Cite

Regioisomers of magnesium(II) phthalocyanine bearing menthol substituents - Synthesis, spectral, electrochemical and computational studies

Cited by 7 publications

References 51 publications

Comparing PVP and Polymeric Micellar Formulations of a PEGylated Photosensitizing Phthalocyanine by NMR and Optical Techniques

Comparing PVP and Polymeric Micellar Formulations of a PEGylated Photosensitizing Phthalocyanine by NMR and Optical Techniques

Octafluoro-Substituted Phthalocyanines of Zinc, Cobalt, and Vanadyl: Single Crystal Structure, Spectral Study and Oriented Thin Films

Phthalocyanines as corrosion inhibitors

Contact Info

Product

Resources

About