The use of bisphthalonitriles in the synthesis of side-strapped 1,11,15,25-tetrasubstituted phthalocyanines

Leznoff, Clifford C.; Drew, D. M.

doi:10.1139/v96-035

Cited by 22 publications

(10 citation statements)

References 25 publications

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“…IR (KBr, cm K1 ): 3330, 2950, 2880, 2240, 1560, 1450, 1390, 1340, 1250, 1190, 1080, 1010, 960, 900, 780; 1 H NMR (400 MHz, d 6 2950,2860,2230,1560,1440,1390,1340,1260,1190,1080,1000,960,900,780 141.42, 132.22, 131.80, 118.14, 114.61, 106.12, 94.97, 75.21, 29.04, 27.43, 21.83, 13.82…”

Section: Methodsmentioning

confidence: 99%

“…IR (KBr, cm K1 ): 2900, 1650, 1350, 1260, 1170, 1130, 1020, 980, 910, 800, 780, 660; 1 H NMR (400 MHz, d 6 2.4. Procedure for preparation of 1,11-bis(p-tosyloxy)-3,6,9-trioxaundecane (5b) [9] A solution of p-toluenesulfonyl chloride (41.94 g, 0.22 mol) in dichloromethane (50 ml) was added dropwise to a mixture of tetraethylene glycol 4b (15.02 g, 0.1 mol), pyridine (18.96 g, 0.24 mol) and dichloromethane (40 ml) at K5 to 5 8C.…”

Section: Methodsmentioning

confidence: 99%

“…Only, spectroscopic data demonstrated that some metals were inserted between two molecules of these phthalocyanines Science and Technology of Advanced Materials 6 (2005) in a sandwich style in a solution [5]. Furthermore, phthalocyanines bearing a 2,2-dialkyl-1,3-propanediol [6] and a binaphthol [7] groups were only synthesized, but no characteristic properties and behaviors were reported. We have focused phthalocyanines including more than two different metals in one molecule, since such phthalocyanine seems to show interesting optical, magnetic and electronic functions.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and behavior of novel phthalocyanines possessing intramolecular crown ether bridges between their different aromatic rings for effective extraction multi metal inclusion

Matsunami

Takaki

Maekawa

et al. 2005

Science and Technology of Advanced Materials

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Novel Cu-and Co-phthalocyanines (7a-e, 8a, b) possessing intramolecular crown ether bridges between their different aromatic rings were successfully synthesized from the reaction of the corresponding bisphthalonitriles (6a-e) bearing polyethyleneoxy chains in the presence of CuCl and CoCl 2 , respectively. As 1,8-diazabicyclo [5.4.0]-7-undecene (DBU) was used as a base in n-pentanol at reflux temperature for 30 h under N 2 atmosphere, these new phthalocyanines were found to be characteristic of satisfactory solubility in some of organic solvents, and showed strong absorption bands in ultraviolet and visible wave length region (l max Z719-739 nm). Extraction experiment of metal chlorides (NaCl, KCl, MgCl 2 , CaCl 2 , CeCl 3 , ZnCl 2 , FeCl 3 ) in chloroform was carried out by using Cu-phthalocyanine (7b) bearing two intramolecular bridges with tri(ethyleneoxy) chains. Among these metal salts, 7b formed a complex (9b) with only FeCl 3 , which showed a dark-red amorphous solid. Spectroscopic analysis of the complex (9b) indicated that original strong absorption bands near 738 nm characteristic for phthalocyanines completely disappeared, and new two strong bands appeared near 799-853 nm. FAB-MASS spectrum of the complex (9b) showed that new strong peaks came out in the region centered at m/zZ1879 and 1881 besides original peaks in the region centered at 1488, which corresponded to molecular peak of the starting phthalocyanine (7b). These facts indicated that the complex (9b) included two molecules of FeCl 3 into the protonated crown ether bridges of the phthalocyanine skeleton. Furthermore, it was found that the complex (9b) was transformed to the original phthalocyanine (7b) quantitatively by treatment with triethylamine. q

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and behavior of novel phthalocyanines possessing intramolecular crown ether bridges between their different aromatic rings for effective extraction multi metal inclusion

Matsunami

Takaki

Maekawa

et al. 2005

Science and Technology of Advanced Materials

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“…The key point in the synthesis of this compound lies in the preparation of the starting material, i.e. 2,2‘-bis(2,3-dicyanophenoxy)biphenyl . Thus, to a dry DMF solution (150 mL) of 15 g (81 mmol) of 1,1‘-biphenyldiol and 6.45 g (60%, 162 mmol) of sodium hydride, which had been cooled to ca.…”

Section: Methodsmentioning

confidence: 99%

An Adjacent Dibenzotetraazaporphyrin: A Structural Intermediate between Tetraazaporphyrin and Phthalocyanine

et al. 1999

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An adjacent dibenzotetraazaporphyrin, in which two benzene units are fused to the adjacent pyrrole rings of tetraazaporphyrin skeleton, has been synthesized as a copper complex for the first time and characterized by electronic absorption and magnetic circular dichroism spectroscopy, by cyclic voltammetry and spectroelectrochemistry using an optically transparent thin layer electrochemical cell. The results were compared with those of tetraazaporphyrin and phthalocyanine analogues. The title compound shows intermediate characteristics between those of normal tetraazaporphyrins and phthalocyanines; the Q-band shifts to the red and becomes more intense while the Soret band broadens with increasing the size of the pi-system. With the expansion of the pi-system, the first reduction potential does not change significantly, while the first oxidation potential shifts negatively, indicating that the LUMO level remains almost constant while the HOMO level destabilizes significantly. These spectroscopic properties and redox potentials were reproduced by molecular orbital calculations within the framework of the Pariser-Parr-Pople approximation. Thermogravimetry analysis suggests that the skeleton of the adjacent dibenzotetraazaporphyrin complex decomposes at about 95 degrees lower than that of the tetra-tert-butylated phthalocyanine analogue.

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“…139 The synthetic strategy for the synthesis of monophthalocyanines using bis(phthalonitrile) precursors was first developed by Leznoff and co-workers for a single-isomer preparation of a tetrasubstituted symmetric phthalocyanine (Scheme 9A). 155 Self-condensation of the 3,3′-bisphthalonitrile leads to the formation of pure 1,11,15,25-tetrasubstituted phthalocyanines 23a-d in 7-21% yields along with polymeric and oligomeric by-products.…”

Section: C)mentioning

confidence: 99%

Synthetic approaches to asymmetric phthalocyanines and their analogues

Nemykin¹,

Dudkin²,

Dumoulin³

et al. 2014

Arkivoc

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This review summarizes synthetic strategies for the preparation of asymmetric phthalocyanines and their analogues. Cross-condensation between two phthalonitrile components, crosscondensation between one phthalonitrile and one non-nitrile component, targeted synthesis of AABB-type compounds, the subphthalocyanine ring-expansion method, as well as postmodification approaches on pre-formed symmetric and asymmetric systems, are discussed. Methodologies for targeted preparation of specific types of asymmetric phthalocyanines and their analogues are also briefly overviewed.

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The use of bisphthalonitriles in the synthesis of side-strapped 1,11,15,25-tetrasubstituted phthalocyanines

Cited by 22 publications

References 25 publications

Synthesis and behavior of novel phthalocyanines possessing intramolecular crown ether bridges between their different aromatic rings for effective extraction multi metal inclusion

Synthesis and behavior of novel phthalocyanines possessing intramolecular crown ether bridges between their different aromatic rings for effective extraction multi metal inclusion

An Adjacent Dibenzotetraazaporphyrin: A Structural Intermediate between Tetraazaporphyrin and Phthalocyanine

Synthetic approaches to asymmetric phthalocyanines and their analogues

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