Synthesis of novel porphyrin and chlorin phosphonic acids and their immobilization on metal oxides

Erbacher, Martin; Montforts, Franz‐Peter

doi:10.1142/s108842461100404x

Cited by 4 publications

(3 citation statements)

References 35 publications

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“…Catalytic transfer hydrogenation also was carried out to obtain 7-H 2 10a( cis ) and 7-H 2 10a( trans ) in 85% yield and 3:2 ratio, respectively (not shown) . The mixture of cis/trans -chlorin–dicarboxylic acids derived from the mixture of 7-H 2 10b( cis ) and 7-H 2 10b( trans ) was subjected to amidation conditions with diethyl 3-aminopropylphosphonate (not shown); the resulting chlorin with two phosphonate feet was attached to a metal-oxide surface for solar cell studies …”

Section: Conversion Of Heme To Gem-dialkylchlorinsmentioning

confidence: 99%

Synthetic Chlorins, Possible Surrogates for Chlorophylls, Prepared by Derivatization of Porphyrins

2016

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Chlorophylls make Earth green, are the central constituents in the engine of photosynthesis, and not surprisingly have garnered immense attention. A chlorin, the core chromophore of a chlorophyll, is a dihydroporphyrin macrocycle that contains one pyrroline ring and three pyrrole rings. The dominant method for the synthesis of chlorins has entailed the derivatization of porphyrins. The present review covers the ostensibly simple conversion of porphyrins, regardless of synthetic or biological origin, to chlorins. The period covered encompasses the entire history since the beginnings of chlorin synthetic chemistry in the early 20th century through 2015. Representative transformations include hydrogenation, cycloaddition, annulation, and diverse "breaking and mending" approaches. Altogether, the synthesis of >1000 chlorins or chlorin-like compounds (containing >50 distinct pyrroline motifs) is described. Such diversity animates the question "what structural features are essential for a chlorin to resemble chlorophyll?" To begin to address the structure-spectrum relationship, > 250 absorption spectra are provided for representative structures. The synthesis and spectral properties of the vast collection of compounds described herein are expected to illuminate the scope to which synthetic chlorins can serve as surrogates for chlorophylls and be exploited in diverse ways.

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Section: Conversion Of Heme To Gem-dialkylchlorinsmentioning

confidence: 99%

Synthetic Chlorins, Possible Surrogates for Chlorophylls, Prepared by Derivatization of Porphyrins

2016

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“…The development of anionic porphyrins, regardless of their high efficiency to produce ROS, does not receive great attention because of their low interaction on the membrane. Anionic porphyrins carry typically sulfonated [ 174 , 175 , 176 , 177 ], carboxylic acid/carboxylate [ 178 , 179 ] or phosphonate/phosphinate groups [ 180 , 181 , 182 ]. These negatively charged functional groups induce an inherent solubility of the porphyrins in aqueous media, which would greatly benefit their application in biological or environmental contexts.…”

Section: Synthetic Access To Cellulose-based Photosensitizersmentioning

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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“…[25][26][27][28][29] Therefor the free carboxylic acid functions of 25, 28 and 31 were utilized to attach aminopropane phosphonate by amide formation. [40][41][42] Activation of carboxylic acid functions and subsequent reaction with aminopropane phosphonate afforded sensitizers 26, 29 and 30 with desired anchoring groups in good yields.…”

Section: Synthesis Of Chlorophyll Based Sensitizersmentioning

confidence: 99%

Synthesis of Donor Substituted Chlorophyll Derivatives for Applications in Dye Sensitized Solar Cells

Conrad‐Fletemeyer,

Dononelli,

Müller‐Bork

et al. 2023

Eur J Org Chem

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Organic dyes based on chlorophyll derivatives were synthesized and investigated with respect to applications in dye sensitized solar cells (DSSCs). Cyanobacterium Spirulina platensis cultivated on large scales in tropical areas around the Pacific Ocean is an attractive source for production and isolation of pure chlorophyll a. Direct transformation of chlorophyll a into very robust chlorin e6 trimethylester 3 affords an ideal platform for synthesis of dyes for artificial photosynthesis. A series of molecules 24 ‐ 32 with donor‐π‐acceptor structures for immobilization on on TiO2 were achieved by subsequent synthetic modifications of 3. Photochemical, theoretical and electrochemical properties of dyes were investigated and their sensitized solar cells performances studied after immobilization on TiO2.

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Synthesis of novel porphyrin and chlorin phosphonic acids and their immobilization on metal oxides

Cited by 4 publications

References 35 publications

Synthetic Chlorins, Possible Surrogates for Chlorophylls, Prepared by Derivatization of Porphyrins

Synthetic Chlorins, Possible Surrogates for Chlorophylls, Prepared by Derivatization of Porphyrins

Porphyrin Photosensitizers Grafted in Cellulose Supports: A Review

Synthesis of Donor Substituted Chlorophyll Derivatives for Applications in Dye Sensitized Solar Cells

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