Porphyrin Analogs Containing Non-Pyrrolic Heterocycles

Brückner, Christian; Akhigbe, Joshua; Samankumara, Lalith P.

doi:10.1142/9789814417297_0001

Cited by 37 publications

(82 citation statements)

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“…Porpholactones, members of the family of so-called pyrrole-modified porphyrins [ 1 ], are porphyrinoids in which a ß,ß’-bond of the parent porphyrin was replaced by a lactone moiety. From the perspective of the tetrapyrrolic structure of porphyrins, a pyrrolic building block was replaced by an oxazolidone ( Scheme 1 ).…”

Section: Introductionmentioning

confidence: 99%

“…The historically first porpholactone, meso -tetraphenylporpholactone (TPL) was derived from meso -tetraphenylporphyrin (TPP) [ 2 ]. While several phenyl- and substituted phenyl-derivatives were reported [ 3 , 4 ], the by far most popular derivative is the meso -tetrakis(pentafluorophenyl)porpholactone (T F PL) and its metal complexes (T F PLM) [ 1 , 5 , 6 ]. This is because of their relative ease of synthesis in one step from T F PP using a number of different methodologies (see below Scheme 2 ) and the multiple possibilities to derivatize the C 6 F 5 -groups by means of nucleophilic aromatic substitution reactions to, for example, render them water-soluble [ 6 , 7 , 8 ].…”

Section: Introductionmentioning

confidence: 99%

“…Multiple distinct pathways of converting (metallo)porphyrins to (metallo)porpholactones were described in nearly two dozen individual papers. Some were specifically developed to provide porpholactones, others became the source of porpholactones by serendipity ( Scheme 2 ) [ 1 , 6 ]. For all methods, the exact mechanisms of the formation of porpholactones are not known.…”

Section: Introductionmentioning

confidence: 99%

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Oxazolochlorins 21. Most Efficient Access to meso-Tetraphenyl- and meso-Tetrakis(pentafluorophenyl)porpholactones, and Their Zinc(II) and Platinum(II) Complexes

2020

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meso-Phenyl- and meso-pentafluorophenyl-porpholactones, their metal complexes, as well as porphyrinoids directly derived from them are useful in a number of technical and biomedical applications, and more uses are expected to be discovered. About a dozen competing and complementary pathways toward their synthesis were reported. The suitability of the methods changes with the meso-aryl group and whether the free base or metal derivatives are sought. These circumstances make it hard for anyone outside of the field of synthetic porphyrin chemistry to ascertain which pathway is the best to produce which specific derivative. We report here on what we experimentally evaluated to be the most efficient pathways to generate the six key compounds from the commercially available porphyrins, meso-tetraphenylporphyrin (TPP) and meso-tetrakis(pentafluorophenyl)porphyrin (TFPP): free base meso-tetraphenylporpholactone (TPL) and meso-tetrakis(pentafluorophenyl)porpholactone (TFPL), and their platinum(II) and zinc(II) complexes TPLPt, TFPLPt, TPLZn, and TFPLZn, respectively. Detailed procedures are provided to make these intriguing molecules more readily available for their further study.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Oxazolochlorins 21. Most Efficient Access to meso-Tetraphenyl- and meso-Tetrakis(pentafluorophenyl)porpholactones, and Their Zinc(II) and Platinum(II) Complexes

2020

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“…Many of these applications would greatly benefit from an inherent solubility of the porphyrins in aqueous media, i.e., not requiring any surfactants or liposome vesicles to mediate solubility. However, even though the methodologies for preparing synthetic porphyrins [ 29 , 30 ], hydroporphyrins [ 2 , 31 , 32 , 33 , 34 ], and their analogues [ 34 , 35 , 36 , 37 , 38 , 39 ], have advanced enormously in the past decades, the vast majority of the synthetic porphyrinoids presented are not natively water-soluble, preventing—or at least complicating—their utilization in, for example, biological contexts.…”

Section: Introductionmentioning

confidence: 99%

Modifications of Porphyrins and Hydroporphyrins for Their Solubilization in Aqueous Media

Luciano

Brückner

2017

Molecules

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The increasing popularity of porphyrins and hydroporphyrins for use in a variety of biomedical (photodynamic therapy, fluorescence tagging and imaging, photoacoustic imaging) and technical (chemosensing, catalysis, light harvesting) applications is also associated with the growing number of methodologies that enable their solubilization in aqueous media. Natively, the vast majority of synthetic porphyrinic compounds are not water-soluble. Moreover, any water-solubility imposes several restrictions on the synthetic chemist on when to install solubilizing groups in the synthetic sequence, and how to isolate and purify these compounds. This review summarizes the chemical modifications to render synthetic porphyrins water-soluble, with a focus on the work disclosed since 2000. Where available, practical data such as solubility, indicators for the degree of aggregation, and special notes for the practitioner are listed. We hope that this review will guide synthetic chemists through the many strategies known to make porphyrins and hydroporphyrins water soluble.

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“…Many of these applications will greatly benefit from an inherent solubility of the porphyrins in aqueous media, i.e., not requiring any surfactants or liposome vesicles to mediate solubility. However, even though the methodologies toward synthetic porphyrins [29,30], hydroporphyrins [2,[31][32][33][34], and their analogues [34][35][36][37][38][39], have advanced enormously in the past decades, the vast majority of the synthetic porphyrinoids presented are not natively water-soluble, preventingor at least complicating-their utilization in, for example, biological contexts.…”

Section: Introductionmentioning

confidence: 99%

Modifications of Porphyrins and Hydroporphyrins for their Solubilization in Aqueous Media

Luciano

Brückner

2017

Preprint

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Abstract:The increasing popularity of porphyrins and hydroporphyrins for application in a variety of biomedical (photodynamic therapy, fluorescence tagging and imaging, photoacoustic imaging) and technical (chemosensing, catalysis, light harvesting) applications is also associated with the growing number of methodologies that enable their solubilization in aqueous media. Natively, the vast majority of synthetic porphyrinic compounds are not water-soluble. Moreover, any water-solubility imposes several restrictions on the synthetic chemist on when to install solubilizing groups in the synthetic sequence, and how to isolate and purify these compounds. This review summarizes the chemical modifications to render synthetic porphyrins water-soluble, with a focus on the work since 2000. Where available, practical data such as solubility, indicators for the degree of aggregation, and special notes for the practicioner are listed. We hope that this review will guide synthetic chemists through the many strategies known to make porphyrins and hydroporphyrins water soluble.

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Porphyrin Analogs Containing Non-Pyrrolic Heterocycles

Cited by 37 publications

References 0 publications

Oxazolochlorins 21. Most Efficient Access to meso-Tetraphenyl- and meso-Tetrakis(pentafluorophenyl)porpholactones, and Their Zinc(II) and Platinum(II) Complexes

Oxazolochlorins 21. Most Efficient Access to meso-Tetraphenyl- and meso-Tetrakis(pentafluorophenyl)porpholactones, and Their Zinc(II) and Platinum(II) Complexes

Modifications of Porphyrins and Hydroporphyrins for Their Solubilization in Aqueous Media

Modifications of Porphyrins and Hydroporphyrins for their Solubilization in Aqueous Media

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