Photoredox properties of tetra-2,3-pyridinoporphyrazines (29H,31H-tetrapyrido[2,3-b: 2′, 3′-g : 2″,3″-l:2‴,3‴-q]porphyrazine)

Wöhrle, Dieter; Gitzel, Jörg; Okura, Ichiro; Aono, Shigetoshi

doi:10.1039/p29850001171

Cited by 75 publications

(39 citation statements)

References 4 publications

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“…Indeed, we have shown that the 2,9,16,23-tetraneopentoxy hthalocyanine zinc(11) (2) derivative exhibited P peaks in its H nmr spectrum, indicating the presence of seven of the possible eight environments collectively present in the four isomers (7). A full discussion of this phenomenon was also recently demonstrated for some quatemized tetra-2,3-pyridinoporphyrazines (8). In this latter example, it was suggested that steric considerations favoured the symmetrical isomer, having C4h syrnrnetry, but that the other isomers were present in lesser amounts.…”

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confidence: 97%

Approaches towards the synthesis of a 2,9,16,23-tetrasubstituted phthalocyanine as a pure isomer

Greenberg¹,

Lever²,

Leznoff³

1988

Can. J. Chem.

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, 1059 (1988). Treatment of 4-neopentoxyphthalonitrile with hydrogen sulfide gas yielded 1-irnino-6-neopentoxy-3-thioisoindoline and 1-irnino-5-neopentoxy-3-thioisoindoline, which on alkylation with iodomethane gave 1 -imino-3-methylthio-6-neopentoxyisoindolenine and 1-imino-3-methylthio-5-neopentoxyisoindolenine. The methylthioisoindolenines readily condensed at room temperature to a mixture of tetrasubstituted phthalocyanines and a series of linear open-chained purple compounds characteristic of isoindigos, while condensation at -20°C in the presence of zinc acetate gave, in at least one experiment, 2,9,16,23-tetraneopentoxyphthalocyanine as a pure isomer. The low temperature formation of phthalocyanines is remarkable and the syntheses described herein provide guidelines for the synthesis of pure isomers of 2,9,16,23-tetrasubstituted phthalocyanines. The purple and red compounds are shown to have isoindigo structures rather than a ring-opened phthalocyanine structure as previously reported.SHAFRIRA GREENBERG, A. B. P. LEVER et CLIFFORD C. LEZNOFF. Can. J. Chem. 66, 1059 (1988). La rkaction du nkopentoxy-4 phtalonitrile et du sulfure d'hydrogbne gazeux conduit i I'imino-1 ntopentoxy-6 thio-3 isoindoline et a I'imino-1 nkopentoxy-5 thio-3 isoindoline qui, par alkylation avec I'iodomkJhane, conduisent B I'imino-1 mkthylthio-3 nkopentoxy-6 isoindoline et a I'imino-1 mkthylthio-3 nkopentoxy-5 isoindoline. A la temptrature ambiante, les mCthylthioisoindolines se condensent facilement pour donner un mklange de phtalocyanines tttrasubstitukes et une strie de composts linkaires pourpres caractkristiques des isoindigos; par ailleurs, une condensation B -20°C, en prtsence d'acttate de zinc, a conduit-au moins dans une experience-i la tttrankopentoxy-2,9,16,23 phtalocyanine sous la forme d'un isomere pur. La formation de phtalocyanines 2 basse tempkrature est remarquable et les synthbses dtcrites dans ce travail fournissent des indications sur les mkthodes de synthese des isombres purs des phtalocyanines substitutes en 2,9,16,23. On a dtmontrt que les composts pourpre et rouge possedent des structures relikes B celle de I'isoindigo plut6t que des structures relikes a celle de la phtalocyanine qui avaient kt6 suggkrkes antkrieurement.[Traduit par la revue]Tetrasubstituted phthalocyanines having one substituent on each of the four benzo rings of phthalocyanine have been known for some time (1) but have received more attention recently due to their importance in electrocatalytic studies (2, 3). Most tetrasubstituted phthalocyanines are prepared by self-condensation of a suitable 3 or 4-substituted phthalonitrile or derivative (4, 5). For example, the isoindoline of 4-neopentoxyphthalonitrile will, upon condensation, give not only 2,9,16,23-tetraneopentoxyphthalocyanine (1) but also the 2,10,16,24-, 2,9,17,24-, and 2,9,16,24-tetraneopentoxyphthalocyanine isomers (6, 7). Indeed, we have shown that the 2,9,16,23-tetraneopentoxy hthalocyanine zinc(11) (2) derivative exhibited P peaks in its H nmr spectrum, indicating the presenc...

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confidence: 97%

Approaches towards the synthesis of a 2,9,16,23-tetrasubstituted phthalocyanine as a pure isomer

Greenberg¹,

Lever²,

Leznoff³

1988

Can. J. Chem.

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“…Interactions of [Pdtmtppa] 4 and [Pttmtppa] 4 with histidine and cysteine have been reported [13]. These complexes were found to be readily reduced at the ring to form [Mtmtppa(À3)] (À3)] 3 , absorbing at 570 nm, and finally in the formation of the doubly reduced [Zntmtppa (À4)] 2 species which showed an absorbance at 500 nm [14]. 4 , allowing the reaction to proceed until there was a definite change in the spectrum, then evaporating the solvent.…”

Section: àmentioning

confidence: 94%

Spectroscopic studies of the interaction of cobalt(II) N,N',N″,N‴-tetramethyltetra-3,4-pyridinoporphyrazine with amino acids and nitrogen oxides

Thamae

Nyokong

2001

J. Porphyrins Phthalocyanines

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“…Cobalt-phthalocyanine (CoPc) and cobalt-hexadecafluorophthalocyanine (16(F)CoPc) were obtained from Aldrich (USA). Cobalt-octaethylhexyloxyphthalocyanine (8b(EH)CoPc) [50], cobalt-tetrapyridinophorphyrazine (4b(Pyr)CoPz), [49] cobalt-tetrapentylopyrrol phthalocyanine (4b(PenPyr)CoPc) [51], cobalt-octahydroxyethanothiolphthalocyanine (8b(SC 2 H 4 OH)CoPc) [52][53] were synthesized according to the literature. Cobalt-tetramethoxyphthalocyanine (8b(MeO)CoPc) was donated by Professor A.…”

Section: Reagents and Solutionsmentioning

confidence: 99%

Optimizing the Electrocatalytic Activity of Surface Confined Co Macrocyclics for the Electrooxidation of Thiocyanate at pH 4

et al. 2011

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We have studied the trends in catalytic activity of several Co macrocyclics confined on the surface graphite electrodes for the oxidation of thiocyanate. A plot of log i (at constant E) versus the formal potential of the catalyst gives a volcano correlation, indicating that the Co(II/I) redox potential needs to be tuned, in order to achieve maximum reactivity. Graphite electrodes modified with Co phthalocyanine at pH 4 exhibit linear amperometric response for thiocyanate concentration in the range 10 À7 and 10 À3 M. Theoretical calculations show that electrocatalytic activity (as log i at constant E) plotted versus the energy of the LUMO of the Co complex also gives a volcano correlation.

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Photoredox properties of tetra-2,3-pyridinoporphyrazines (29H,31H-tetrapyrido[2,3-b: 2′, 3′-g : 2″,3″-l:2‴,3‴-q]porphyrazine)

Abstract: 2,3‐Dicyanopyridin und das Metallacetat [ohne Metallsalz für den freien Liganden (Ia)] werden in wasserfreiem N,N‐Dimethylaminoethanol (24 h, 130°C) zu den Verbindungen (I) umgesetzt.

Cited by 75 publications

References 4 publications

Approaches towards the synthesis of a 2,9,16,23-tetrasubstituted phthalocyanine as a pure isomer

Approaches towards the synthesis of a 2,9,16,23-tetrasubstituted phthalocyanine as a pure isomer

Spectroscopic studies of the interaction of cobalt(II) N,N',N″,N‴-tetramethyltetra-3,4-pyridinoporphyrazine with amino acids and nitrogen oxides

Optimizing the Electrocatalytic Activity of Surface Confined Co Macrocyclics for the Electrooxidation of Thiocyanate at pH 4

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