Sythesis and Characterisation of New 2-Diazo-3-Oxo-5,10,15,2o-Tetraphenylchlorins

Cavaleiro, José A. S.; Gerdan, Viviana M.; Hombrecher, Hermann K.; Neves, Maria G. P. M. S.; Silva, Artur M. S.

doi:10.1515/hc.1997.3.3.253

Cited by 5 publications

(3 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The results for several metalloporphyrins are shown in Table 28. 497 The resulting 17-oxo-18-diazochlorins (type B2) are stable compounds and could be stored at room temperature for one month, and also did not show any decomposition in refluxing THF or chloroform for 48 h.…”

Section: Breaking and Mending Strategiesmentioning

confidence: 99%

“…Oxidation of a β-aminoporphyrin with NaNO 2 and sulfuric acid in hydrogen peroxide afforded the corresponding 17-oxo-18-diazochlorin (type B2 ). The results for several metalloporphyrins are shown in Table . The resulting 17-oxo-18-diazochlorins (type B2 ) are stable compounds and could be stored at room temperature for one month, and also did not show any decomposition in refluxing THF or chloroform for 48 h.…”

Section: Alternative Pyrroline Motifsmentioning

confidence: 99%

See 1 more Smart Citation

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

2016

View full text Add to dashboard Cite

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.

show abstract

Section: Breaking and Mending Strategiesmentioning

confidence: 99%

Section: Alternative Pyrroline Motifsmentioning

confidence: 99%

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

2016

View full text Add to dashboard Cite

show abstract

“…2-Diazo-3-oxochlorins (that can be prepared in good yields from 2-aminoporphyrins [75] or 2,3-dioxochlorins [76]) undergo photodecomposition, with extrusion of N 2 , to yield a mixture of porphyrin derivatives. The product distribution strongly depends upon the central metal ion and the presence or absence of nucleophilic substrates [77,78,79,80].…”

Section: Chemistrymentioning

confidence: 99%

Porphyrin Macrocycle Modification: Pyrrole Ring-Contracted or -Expanded Porphyrinoids

Costa

Tomé

2016

Molecules

View full text Add to dashboard Cite

Abstract:In recent years, several synthetic strategies aiming at the peripheral functionalization of porphyrins were developed. Particularly interesting are those involving the modification of β-pyrrolic positions leading to pyrrole-modified porphyrins containing four-, five-, six-or seven-membered heterocycles. Azeteoporphyrins, porpholactones and morpholinoporphyrins are representative examples of such porphyrinoids. These porphyrin derivatives have recently gained an increasing interest due to their potential application in PDT, as multimodal imaging contrast agents, NIR-absorbing dyes, optical sensors for oxygen, cyanide, hypochlorite and pH, and in catalysis.

show abstract

Expansion and contraction: Shaping the porphyrin boundary via diradical reactivity

Boerner

Dye

Köpke

et al. 2013

Coordination Chemistry Reviews

View full text Add to dashboard Cite

Sythesis and Characterisation of New 2-Diazo-3-Oxo-5,10,15,2o-Tetraphenylchlorins

Abstract: The Cu and Ni derivatives of ß-amino-5,10,15,20-tetraphenylporphyrin react with sodium nitrite in THF by formation of 2-diazo-3-oxo-5,10,15,20-tetraphenylchlorins. The spectroscopic properties and some electrochemical properties of the synthesised compounds were investigated.

Cited by 5 publications

References 8 publications

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

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

Porphyrin Macrocycle Modification: Pyrrole Ring-Contracted or -Expanded Porphyrinoids

Expansion and contraction: Shaping the porphyrin boundary via diradical reactivity

Contact Info

Product

Resources

About