Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 1—Azides, Porphyrins and Corroles

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/molecules25071662

Cited by 11 publications

(7 citation statements)

References 133 publications

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“…In general, these entities are introduced by making use of silicon reactants bearing hydrolysable groups (typically alkoxy, acyloxy, amine, or chlorine) that can react with hydroxyl groups on cellulose ( Figure 3 , path g). The non-hydrolysable unit typically holds a moiety that can react with a biologically active molecule [ 121 , 122 ].…”

Section: Functionalization Of Cellulose Supportsmentioning

confidence: 99%

Porphyrin Photosensitizers Grafted in Cellulose Supports: A Review

Monteiro

Neves

Nativi

et al. 2023

IJMS

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Cellulose is the most abundant natural biopolymer and owing to its compatibility with biological tissues, it is considered a versatile starting material for developing new and sustainable materials from renewable resources. With the advent of drug-resistance among pathogenic microorganisms, recent strategies have focused on the development of novel treatment options and alternative antimicrobial therapies, such as antimicrobial photodynamic therapy (aPDT). This approach encompasses the combination of photoactive dyes and harmless visible light, in the presence of dioxygen, to produce reactive oxygen species that can selectively kill microorganisms. Photosensitizers for aPDT can be adsorbed, entrapped, or linked to cellulose-like supports, providing an increase in the surface area, with improved mechanical strength, barrier, and antimicrobial properties, paving the way to new applications, such as wound disinfection, sterilization of medical materials and surfaces in different contexts (industrial, household and hospital), or prevention of microbial contamination in packaged food. This review will report the development of porphyrinic photosensitizers supported on cellulose/cellulose derivative materials to achieve effective photoinactivation. A brief overview of the efficiency of cellulose based photoactive dyes for cancer, using photodynamic therapy (PDT), will be also discussed. Particular attention will be devoted to the synthetic routes behind the preparation of the photosensitizer-cellulose functional materials.

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Section: Functionalization Of Cellulose Supportsmentioning

confidence: 99%

Porphyrin Photosensitizers Grafted in Cellulose Supports: A Review

Monteiro

Neves

Nativi

et al. 2023

IJMS

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“…Most recently, K. B. Sharpless shared the 2022 Nobel Prize in Chemistry with C. R. Bertozzi and M. Meldal for the development of click chemistry and bioorthogonal chemistry. Due to high product yields, quick reaction times, and excellent regioselectivity, the "click" cycloaddition reaction has enabled the synthesis of several compounds with a wide range of applications in a variety of sectors, including bioconjugation [ 5 – 6 ] drug development [ 7 – 8 ], glycoscience [ 9 – 10 ], porphyrin chemistry [ 11 ], nanoscience [ 12 ], and materials research [ 13 – 14 ].…”

Section: Introductionmentioning

confidence: 99%

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

Singh¹

2023

Beilstein J. Org. Chem.

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Among all the available approaches in organic synthesis, the “click chemistry” protocol is very common nowadays to covalently connect two diverse moieties in a single framework. Therefore, this review focuses on the synthesis and photophysical studies of β- and meso-substituted and 1,2,3-triazole-fused porphyrin conjugates. All of the porphyrin conjugates discussed here are synthesized via a copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction between an azide and a terminal alkyne, also popular as "click reaction" or CuAAC reaction. Moreover, the 1,2,3-triazole ring also serves as a spacer and an electron transfer bridge between the porphyrin and the attached chromophores. In order to provide a critical overview of the synthesis and properties of various porphyrin-triazole hybrids, this review will discuss some of the key reactions involved in the preparation of triazole-linked porphyrin conjugates.

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“…Although the syntheses of variously substituted free-base and metalated porphyrins have been extensively studied, − synthetic routes to hydroporphyrins are under active investigation due to the structural challenges associated with these fascinating molecules. Similarly, new methods dominate the syntheses of variously substituted free-base and metalated chlorins − and corroles, − with interest in TDCs only recently beginning to emerge. , A key feature of the structure of corrins is the presence of a gem-dialkyl group in each reduced ring, stabilizing the highly reduced macrocycle. Similar stabilizing features are essential in synthetic dehydrocorrins.…”

Section: Introductionmentioning

confidence: 99%

Syntheses and Properties of Metalated Tetradehydrocorrins

et al. 2022

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The monoanionic tetrapyrrolic macrocycle B,C-tetradehydrocorrin (TDC) resides chemically between corroles and corrins. This chemical space remains largely unexplored due to a lack of reliable synthetic strategies. We now report the preparation and characterization of Co(II)- and Ni(II)-metalated TDC derivatives ([Co-TDC]+ and [Ni-TDC]+ , respectively) with a combination of crystallographic, electrochemical, computational, and spectroscopic techniques. [Ni-TDC]+ was found to undergo primarily ligand-centered electrochemical reduction, leading to hydrogenation of the macrocycle under cathodic electrolysis in the presence of acid. Transient absorption (TA) spectroscopy reveals that [Ni-TDC]+ and the two-electron-reduced [Ni-TDC]− possess long-lived excited states, whereas the excited state of singly reduced [Ni-TDC] exhibits picosecond dynamics. The Co(I) compound [Co-TDC] is air stable, highlighting the notable property of the TDC ligand to stabilize low-valent metal centers in contradistinction to other tetrapyrroles such as corroles, which typically stabilize metals in higher oxidation states.

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Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 1—Azides, Porphyrins and Corroles

Cited by 11 publications

References 133 publications

Porphyrin Photosensitizers Grafted in Cellulose Supports: A Review

Porphyrin Photosensitizers Grafted in Cellulose Supports: A Review

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

Syntheses and Properties of Metalated Tetradehydrocorrins

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