Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 2—Azides, Phthalocyanines, Subphthalocyanines and Porphyrazines

Araújo, Ana R. L.; Tomé, Augusto C.; Santos, Carla I. M.; Faustino, Maria A. F.; Neves, Maria G. P. M. S.; Simões, Mário M. Q.; Moura, Nuno M. M.; Abu‐Orabi, Sultan T.; Cavaleiro, José A. S.

doi:10.3390/molecules25071745

Cited by 9 publications

(5 citation statements)

References 57 publications

(69 reference statements)

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“…85 Copper( i )-catalyzed azide-alkyne cycloaddition reactions (CuAAC) have been carried out from axially azido-substituted SubPcs 85,138 and ethynyl-substituted SubPcs. 72,136,138–140,167,168 SubPcs with terminal alkyne substituent have been employed in Pd-catalyzed oxidative Glaser–Hay coupling, 72,75,138 modified Cadiot–Chodkiewicz coupling 72,75,90 and Sonogashira coupling 57,58,72,75,90 reactions. Sonogashira cross-coupling reactions from the apical bromophenoxy group 169 and Suzuki cross-coupling either from iodophenoxy or borylated phenylacetylene with boronic acid and halogenated derivatives 170,171 have also been carried out.…”

Section: Subphthalocyaninesmentioning

confidence: 99%

Recent advances in subphthalocyanines and related subporphyrinoids

et al. 2022

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Section: Subphthalocyaninesmentioning

confidence: 99%

Recent advances in subphthalocyanines and related subporphyrinoids

et al. 2022

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“…As was stated by C. F. van Nostrum et al, the metal ions in the coordination centers and the peripheral substituents strongly influence the electronic absorption spectra of the porphyrinoids [29]. In general, in the spectra of Pzs, two characteristic bands can be observed, the Soret band (B-band) in the range of 300-400 nm and the Q-band in the range of 600-850 nm [29][30][31][32]. The Q-bands that appeared in the spectra of both Pzs 6 and 7 recorded in different solvents are presented in Figure 1.…”

Section: Absorption Properties Of New Porphyrazinesmentioning

confidence: 99%

Zinc(II) Sulfanyltribenzoporphyrazines with Bulky Peripheral Substituents—Synthesis, Photophysical Characterization, and Potential Photocytotoxicity

et al. 2022

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The study’s aim was to synthesize new unsymmetrical sulfanyl zinc(II) porphyrazines and subject them to physicochemical and electrochemical characterization and also an initial acute toxicity assessment. The procedure was initiated from a commercially available dimercaptomaleonitrile disodium salt and o-phthalonitrile using Linstead’s macrocyclization reaction conditions, which led to magnesium(II) tribenzoporphyrazine with 4-(3,5-dibutoxycarbonylphenoxy)butylthio substituents. The obtained macrocycle was demetallated with trifluoroacetic acid and subsequently remetallated with zinc(II) acetate toward the zinc(II) porphyrazine derivative. The zinc(II) tribenzoporphyrazine with 4-(3,5-dibutoxycarbonylphenoxy)butylthio substituents was then subjected to the reduction reaction with LiAlH4, yielding zinc(II) tribenzoporphyrazine with 4-[3,5-di(hydroxymethyl)phenoxy]butylthio substituents. The new zinc(II) tribenzoporphyrazines were characterized by UV-Vis spectroscopy, various NMR techniques (1HNMR, 13CNMR, 1H-1H COSY, 1H-13C HSQC, and 1H-13C HMBC), and mass spectrometry. In the UV-Vis spectra, both macrocycles revealed characteristic Soret and Q-bands, whose positions were dependent on the solvent used for the measurements. Zinc(II) tribenzoporphyrazines were studied using electrochemical and photochemical methods, including the singlet oxygen generation assessment. Both zinc(II) porphyrazines revealed high singlet oxygen generation quantum yield values of up to 0.59 in DMSO, which indicates their potential photosensitizing potential for photodynamic therapy. In addition, new derivatives were subjected to a Microtox® bioluminescence assay.

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“…Similar to corroles and porphyrins, the synthesis of both symmetric as well as asymmetric phthalocyanines has been described. Fine-tuning of solubility properties in a variety of common organic solvents as well as water is possible via the addition and incorporation of appropriate substituents (Sakamoto and Ohno-Okumura, 2009;Sorokin, 2013;Nemykin et al, 2014;Denekamp et al, 2019;Araújo et al, 2020).…”

Section: Porphyrins Corroles and Phthalocyaninesmentioning

confidence: 99%

Recent Progress in (Photo-)-Electrochemical Conversion of CO2 With Metal Porphyrinoid-Systems

et al. 2021

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Since decades, the global community has been facing an environmental crisis, resulting in the need to switch from outdated to new, more efficient energy sources and a more effective way of tackling the rising carbon dioxide emissions. The activation of small molecules such as O2, H+, and CO2 in a cost—and energy-efficient way has become one of the key topics of catalysis research. The main issue concerning the activation of these molecules is the kinetic barrier that has to be overcome in order for the catalyzed reaction to take place. Nature has already provided many pathways in which small molecules are being activated and changed into compounds with higher energy levels. One of the most famous examples would be photosynthesis in which CO2 is transformed into glucose and O2 through sunlight, thus turning solar energy into chemical energy. For these transformations nature mostly uses enzymes that function as catalysts among which porphyrin and porphyrin-like structures can be found. Therefore, the research focus lies on the design of novel porphyrinoid systems (e.g. corroles, porphyrins and phthalocyanines) whose metal complexes can be used for the direct electrocatalytic reduction of CO2 to valuable chemicals like carbon monoxide, formate, methanol, ethanol, methane, ethylene, or acetate. For example the cobalt(III)triphenylphosphine corrole complex has been used as a catalyst for the electroreduction of CO2 to ethanol and methanol. The overall goal and emphasis of this research area is to develop a method for industrial use, raising the question of whether and how to incorporate the catalyst onto supportive materials. Graphene oxide, multi-walled carbon nanotubes, carbon black, and activated carbon, to name a few examples, have become researched options. These materials also have a beneficial effect on the catalysis through for instance preventing rival reactions such as the Hydrogen Evolution Reaction (HER) during CO2 reduction. It is very apparent that the topic of small molecule activation offers many solutions for our current energy as well as environmental crises and is becoming a thoroughly investigated research objective. This review article aims to give an overview over recently gained knowledge and should provide a glimpse into upcoming challenges relating to this subject matter.

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Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 2—Azides, Phthalocyanines, Subphthalocyanines and Porphyrazines

Cited by 9 publications

References 57 publications

Recent advances in subphthalocyanines and related subporphyrinoids

Recent advances in subphthalocyanines and related subporphyrinoids

Zinc(II) Sulfanyltribenzoporphyrazines with Bulky Peripheral Substituents—Synthesis, Photophysical Characterization, and Potential Photocytotoxicity

Recent Progress in (Photo-)-Electrochemical Conversion of CO2 With Metal Porphyrinoid-Systems

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