Names | |
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IUPAC name
Porphyrazine
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Other names
5,10,15,20-Tetraazaporphine; Tetraazaporphine; Tetraazaporphyrin; Tetrazaporphin
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Identifiers | |
3D model (
JSmol)
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ChemSpider | |
PubChem
CID
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CompTox Dashboard (
EPA)
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Properties | |
C16H10N8 | |
Molar mass | 314.312 g·mol−1 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Porphyrazines, or tetraazaporphyrins, are tetrapyrrole macrocycles similar to porphyrins and phthalocyanines. Pioneered by Sir R. Patrick Linstead as an extension of his work on phthalocyanines, [1] porphyrazines differ from porphyrins in that they contain -meso nitrogen atoms, rather than carbon atoms, and differ from phthalocyanines in that their β-pyrrole positions are open for substitution. These differences confer physical properties that are distinct from both porphyrins and phthalocyanines. [2]
Porphyrazines are prepared by magnesium templated cyclization of maleonitriles. [3] Cross-cyclization with phthalonitrile or diiminoisoindole derivatives is possible introducing a flexibile synthetic route that has led to the synthesis of porphyrazines with peripheral heterocyclic rings, [4] heteroatom substituents (S, O, N), [5] peripherally bound metal atoms, [6] and mixed -benzo porphyrazine systems. [7]
Porphyrazines are most well known for their intense electronic absorption throughout the UV, visible, and NIR spectral regions. Electronic absorption spectra for porphyrazines are similar to those of phthalocyanines, [8] with an intense Soret band (λ ≈ 300 - 400 nm) and Q-band (λ > 600 nm). [7] [9]
Porphyrazines exhibit fluorescence from the first excited singlet state (S1 → S0) [10] at visible and NIR wavelengths which is typical of tetrapyrrole macrocycles. Dual-emission from organic fluorophores is not common but, as observed in phthalocyanines, [11] [12] violet emission from an upper excited state (S2 → S0) is observed in porphyrazines. [13] [14] [15]
Names | |
---|---|
IUPAC name
Porphyrazine
| |
Other names
5,10,15,20-Tetraazaporphine; Tetraazaporphine; Tetraazaporphyrin; Tetrazaporphin
| |
Identifiers | |
3D model (
JSmol)
|
|
ChemSpider | |
PubChem
CID
|
|
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C16H10N8 | |
Molar mass | 314.312 g·mol−1 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Porphyrazines, or tetraazaporphyrins, are tetrapyrrole macrocycles similar to porphyrins and phthalocyanines. Pioneered by Sir R. Patrick Linstead as an extension of his work on phthalocyanines, [1] porphyrazines differ from porphyrins in that they contain -meso nitrogen atoms, rather than carbon atoms, and differ from phthalocyanines in that their β-pyrrole positions are open for substitution. These differences confer physical properties that are distinct from both porphyrins and phthalocyanines. [2]
Porphyrazines are prepared by magnesium templated cyclization of maleonitriles. [3] Cross-cyclization with phthalonitrile or diiminoisoindole derivatives is possible introducing a flexibile synthetic route that has led to the synthesis of porphyrazines with peripheral heterocyclic rings, [4] heteroatom substituents (S, O, N), [5] peripherally bound metal atoms, [6] and mixed -benzo porphyrazine systems. [7]
Porphyrazines are most well known for their intense electronic absorption throughout the UV, visible, and NIR spectral regions. Electronic absorption spectra for porphyrazines are similar to those of phthalocyanines, [8] with an intense Soret band (λ ≈ 300 - 400 nm) and Q-band (λ > 600 nm). [7] [9]
Porphyrazines exhibit fluorescence from the first excited singlet state (S1 → S0) [10] at visible and NIR wavelengths which is typical of tetrapyrrole macrocycles. Dual-emission from organic fluorophores is not common but, as observed in phthalocyanines, [11] [12] violet emission from an upper excited state (S2 → S0) is observed in porphyrazines. [13] [14] [15]