187. Phthalocyanines. Part IX. Derivatives of thiophen, thionaphthen, pyridine, and pyrazine, and a note on the nomenclature

Linstead, R. P.; Noble, E. G.; Wright, Justin M.

doi:10.1039/jr9370000911

Cited by 105 publications

(58 citation statements)

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“…It is known that PC hetero analogs are prone to form hydrates (14,19). Accordingly, we dehydrated the analytical samples of complexes 6a,b and 7a-g by heating in acetic anhydride.…”

Section: Precursorsmentioning

confidence: 99%

Substituted tetra-2,3-pyrazinoporphyrazines. Part I. Angular annelation of tetra-2,3-quinoxalinoporphyrazine

Kudrevich¹,

Lier²,

Gal'pern³

et al. 1996

Can. J. Chem.

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Several derivatives of 2,3-dicyanopyrazine were prepared via the condensation of o-quinones with diaminomaleodinitrile. BenzoV]quinoxaline-2,3-dinitrile was obtained from 1,2-naphthoquinone, and a series of isomeric, ditert-butyl substituted 5,6-(9,lO-phenanthro)-2.3-dicyanopyrazines were prepared from the corresponding di-tert-butyl-9,lOphenanthrenequinones. Complexation of benzov]quinoxaline-2.3-dinitrile, and unsubstituted 5,6-(9,lO-phenanthr0)-2,3-dicyanopyrazine, with an appropriate metal salt yielded metal complexes of tetra-2,3-(benzov]quinoxalino)porphyrazine and tetra-2.3-[5,6-(9.10-phenanthro)]porphyrazine, respectively. Metal-free tetra-2,3-[5,6-(9,lO-phenanthro)porphyrazine was obtained from the dilithium derivative by demetallation in HCI. These compounds have limited solubility in organic solvents, such as quinoline, and are aggregated in solutions. To eliminate the aggregation phenomenon and to determine the spectral properties of angularly annelated naphthalocyanine aza analogs, we prepared several isomeric tetra-2.3-[5,6-(di-tert-butyl-9,lOphenanthro)pyrazino]porphyrazines. These octa(tert-butyl) substituted complexes were synthesized via complexation of di-tertbutyl substituted 5,6-(9,lO-phenanthro)-2,3-dicyanopyrazines with metal salts in the presence of urea, quinoline, and tri(nbutyl)amine, and purified by silica gel chromatography. They are soluble in chloroform and substantially monomerized in solutions. A hypsochromic shift of the Q-band of octaaza naphthalocyanines versus their carbocyclic analogs was observed for all aza analogs, with the extent of the shift depending on the composition of the aromatic macrocycle. Thus, the first angularly annelated benzo ring addition causes a hypsochromic shift (-25 nm) of the Q-band of tetra-2,3-quinoxalinoporphyrazine, whereas addition of a second condensed benzo ring has little effect.Key words: phthalocyanine, aza analog, tetra-2,3-quinoxalinoporphyrazine, angular annelation.RCsurnC : Plusieurs derives de 2,3-dicyanopyrazine ont CtC prCparCs via la condensation de o-quinones avec le diaminomaleodinitrile. Le benzov]quinoxaline-2,3-dinitrile a Ct C obtenu de la 1,2-naphthoquinone et plusieurs isomkres de ditert-butyl-5,6-(9,1O-phenanthro)-2,3-dicyanopyrazines ont Ct C preparks B partir des di-tert-butyl-9,lO-phenanthrenequinones correspondants. La condensation de benzo(jquinoxaline-2,3-dinitrile et de 5,6-(9,lO-phenanthr0)-2,3-dicyanopyrazine non substituC avec un sel du metal appropriC a produit des complexes mCtalliques de tetra-2,3-(benzov]quinoxalino)porphyrazine et de tetra-2,3-[5,6-(9.10-phenanthrolporphyrazine, respectivement. La tetra-2,3-[5,6-(9,lO-phenanthro)porphyrazine sans mCtal a CtC obtenu du dCrivC de dilithium par la dCmCtallisation dans HCI. Ces composCs ont une solubilitC limitCe dans les solvants organiques tels que la quinoline et sont agrCgCs dans les solutions. Afin d'iliminer le phCnomene d'agrkgation et pour dCterminer les propriCtes spectrales des azaanalogues de naphthalocyanine avec d'anneaux angulaires condens...

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“…It is known that PC hetero analogs are prone to form hydrates (14,19). Accordingly, we dehydrated the analytical samples of complexes 6a,b and 7a-g by heating in acetic anhydride.…”

Section: Precursorsmentioning

confidence: 99%

Substituted tetra-2,3-pyrazinoporphyrazines. Part I. Angular annelation of tetra-2,3-quinoxalinoporphyrazine

Kudrevich¹,

Lier²,

Gal'pern³

et al. 1996

Can. J. Chem.

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“…High resolution MALDI mass spectra were registered on a Bruker ULTRAFLEX II TOF/TOF instrument with DCTB as the matrix. 1 …”

Section: Methodsmentioning

confidence: 99%

“…The square-wave voltammogram (SWVA) exhibited three reduction potentials at -0.915, -1.295 and -1.735 V and two oxidation potentials at +0.835 and +1.520 V. In cyclic voltammogram (CVA), only highly-reversible redox processes Red 1 , Red 2 and Ox 1 were observed, which is likely due to the lower sensitivity of the method. Under the potential scanning until 1.6 V and higher, poor reversibility of the Ox 2 process resulted in a decrease of intensity and a shift of the reverse peak of Ox 1 .…”

Section: Treatment Of Magnesium Complexmentioning

confidence: 99%

“…UV-Vis (THF) λ max nm (lgε): 665 (4.6), 603 (3.9), 367 (4.4). 1 c) Approach with pyridine hydrochloride. A mixture of 3 (0.030 g, 0.0370 mmol) and pyridine hydrochloride (0.012 g, 0.10 mmol) were refluxed in pyridine (600 μl) for 3 h. The reaction mixture was cooled to room temperature and a mixture MeOH:H 2 O (10:1 V/V) was added.…”

Section: 38914152021-octakis[4΄5΄6΄7΄-tetrahydrobenzo]-tetmentioning

confidence: 99%

“…[1] The presence of a sulphur-containing heterocyclic moiety in the macrocycle improves photoconductivity [2] and nonlinear optical (NLO) properties.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Study of Physicochemical Properties of New Substituted Tetrathieno[2,3-b]porphyrazines

Dubinina¹,

Dyumaeva²,

Trashin³

et al. 2012

MHC

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Synthetic approach to a new substituted tetrathieno [2,3-b]porphyrazine, its planar and sandwich-type complexes was developed. Aggregation phenomena and spectral properties of the target compounds were investigated by UVVis spectroscopy and AFM. Electrochemical behaviour of the Zn complex was studied in a wide range of potentials (-2.0÷2.0 V). The NLO properties of Zn complex was studied by the z-scan approach.

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Tetrakis(selenodiazole)porphyrazines 1: Tetrakis(selenodiazole)porphyrazine and its Mg(II) and Cu(II) Derivatives. Evidence for their Conversion to Tetrakis(pyrazino)porphyrazines through Octaaminoporphyrazines

Bauer

Ercolani

Galli

et al. 1999

J. Porphyrins Phthalocyanines

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The new phthalocyanine-like macrocycle tetrakis(selenodiazole)porphyrazine, TSeDPzH 2, and its Mg ( II ) and Cu ( II ) complexes have been prepared and their general, spectroscopic (IR, UV-vis), and magnetic properties investigated. It has been observed that the peripheral selenodiazole rings of the TSeDPz skeleton can be opened by the action of H 2 S , with release of the Se atoms and formation of a new macrocycle, i.e. octaaminoporphyrazine, which is easily converted into tetrakis(pyrazino)porphyrazine derivatives.

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187. Phthalocyanines. Part IX. Derivatives of thiophen, thionaphthen, pyridine, and pyrazine, and a note on the nomenclature

Cited by 105 publications

References 0 publications

Substituted tetra-2,3-pyrazinoporphyrazines. Part I. Angular annelation of tetra-2,3-quinoxalinoporphyrazine

Substituted tetra-2,3-pyrazinoporphyrazines. Part I. Angular annelation of tetra-2,3-quinoxalinoporphyrazine

Synthesis and Study of Physicochemical Properties of New Substituted Tetrathieno[2,3-b]porphyrazines

Tetrakis(selenodiazole)porphyrazines 1: Tetrakis(selenodiazole)porphyrazine and its Mg(II) and Cu(II) Derivatives. Evidence for their Conversion to Tetrakis(pyrazino)porphyrazines through Octaaminoporphyrazines

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