ChemInform Abstract: THE SOLID PHASE SYNTHESIS OF UNSYMMETRICAL PHTHALOCYANINES

Hall, T. W.; Greenberg, S D; McArthur, Colin R.; Khouw, B.; Leznoff, Clifford C.

doi:10.1002/chin.198325326

Cited by 19 publications

(26 citation statements)

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“…93,94 Because of the nature of this synthetic strategy, it used exclusively for preparation of the A 3 B type of phthalocyanines (Scheme 4A). In this approach, a 4-substituted phthalonitrile or 1,3-diiminoisoindoline (B) is first coupled, usually using ether bond formation, to an appropriately functionalized polymer.…”

Section: Polymer Support-based Approachmentioning

confidence: 99%

“…Such phthalonitrile or 1,3-diiminoisoindoline containing polymer then reacted with a large excess of second phthalonitrile or 1,3-diiminoisoindoline (A) in appropriate solvent, which solubilize A but not polymer-supported B. [93][94][95] Symmetric phthalocyanine A 4 , which is the major reaction product could be removed by simple washing of the reaction mixture with organic solvent, while polymer-bound asymmetric A 3 B compound 7 remains insoluble. Further treatment of the polymer-bound asymmetric A 3 B phthalocyanine with an acid cleaves polymer backbone and liberates the target A 3 B compound 8 into solution, which can be filtered from the remaining insoluble polymeric support.…”

Section: Polymer Support-based Approachmentioning

confidence: 99%

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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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Section: Polymer Support-based Approachmentioning

confidence: 99%

Section: Polymer Support-based Approachmentioning

confidence: 99%

Synthetic approaches to asymmetric phthalocyanines and their analogues

Nemykin¹,

Dudkin²,

Dumoulin³

et al. 2014

Arkivoc

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“…Although symmetrical tetra-and octasubstituted phthalocyanines are well known, the synthesis of simple mono-and disubstituted and other unsymmetrical phthalocyanines remains a difficult problem (10-21). For instance, all tetrasubstituted phthalocyanines so far synthesized contain one substituent in each of the benzene rings, and no phthalocyanines such as 1,2,3,4-or 1,2,3,8-tetrasubstituted phthalocyanines have been reported.Successful methods for the synthesis of unsymmetrical phthalocyanines can be divided into three groups according to strategy: (1) the polymer support route (14,16,19,20); (2) the homogeneous mixed condensation route ( 12-14, 2 1); and (3) the subphthalocyanine route (1 1). There are difficulties with all three routes for large-scale preparation of unsymmetrical alkoxy-substituted phthalocyanines.…”

mentioning

confidence: 99%

“…Thus, unsymmetrical phthalocyanines are important goals in synthesis. Although symmetrical tetra-and octasubstituted phthalocyanines are well known, the synthesis of simple mono-and disubstituted and other unsymmetrical phthalocyanines remains a difficult problem (10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21). For instance, all tetrasubstituted phthalocyanines so far synthesized contain one substituent in each of the benzene rings, and no phthalocyanines such as 1,2,3,4-or 1,2,3,8-tetrasubstituted phthalocyanines have been reported.…”

mentioning

confidence: 99%

“…Successful methods for the synthesis of unsymmetrical phthalocyanines can be divided into three groups according to strategy: (1) the polymer support route (14,16,19,20); (2) the homogeneous mixed condensation route ( 12-14, 2 1); and (3) the subphthalocyanine route (1 1). There are difficulties with all three routes for large-scale preparation of unsymmetrical alkoxy-substituted phthalocyanines.…”

mentioning

confidence: 99%

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Phthalocyanine-modified silica gels and their application in the purification of unsymmetrical phthalocyanines

Leznoff¹,

McArthur²,

Qin³

1993

Can. J. Chem.

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Five species of phthalocyanine-modified silica gels were prepared. The loadings of phthalocyanine on these silica gels were determined by acidic hydrolysis. The concept of using the aggregation phenomenon to advantage to aid chromatographic separation of unsymmetrical phthalocyanines was investigated by employing these modified silica gels as chromatographic media to purify unsymmetrical phthalocyanines. Four groups of phthalocyanine mixtures were prepared by mixed condensation. One of the desired unsymmetrical phthalocyanines was successfully purified by conventional column chromatography while others were separated by the new method described herein. CLIFFORD C. LEZNOFF, COLIN R. MCARTHUR et YONGNIAN QIN. Can. J. Chem. 71, 13 19 (1993).On a prepare cinq espitces de gels de silice modifiCs par des phtalocyanines. On a determine la quantitC de phtalocyanine presente sur ces gels de silice en faisant appel B une hydrolyse acide. On a CtudiC le concept de l'utilisation du phenomkne d'agregation pour faciliter la sCparation chromatographique de phtalocyanines non symktriques en utilisant ces gels de silice modifies comme milieux chromatographiques pour la purification de phtalocyanines non symktriques. On a prCparC quatre groupes de mClanges de phtalocyanines par condensations mixtes. On a rCussi a purifier une des phtalocyanines non symCtriques dCsirCes par chromatographie conventionnelle sur colonne alors que les autres ont CtC sCparCes par la mCthode dCcrite ici.[Traduit par la rCdaction]Unsymmetrical phthalocyanines present challenges in the development of new methods of synthesis and separation. The potential use of phthalocyanines for photodynamic therapy (PDT) of cancer has sparked considerable interest in the photobiology of these compounds (1-9). To find a suitable phthalocyanine as photosensitizer, it is necessary to tune the position of its absorption band. Such fine tuning can be achieved by the stepwise introduction of peripheral substituent groups or by the stepwise adjustment of the size of the T-conjugated macrocyclic systems (10-13). Thus, unsymmetrical phthalocyanines are important goals in synthesis. Although symmetrical tetra-and octasubstituted phthalocyanines are well known, the synthesis of simple mono-and disubstituted and other unsymmetrical phthalocyanines remains a difficult problem (10-21). For instance, all tetrasubstituted phthalocyanines so far synthesized contain one substituent in each of the benzene rings, and no phthalocyanines such as 1,2,3,4-or 1,2,3,8-tetrasubstituted phthalocyanines have been reported.Successful methods for the synthesis of unsymmetrical phthalocyanines can be divided into three groups according to strategy: (1) the polymer support route (14,16,19,20); (2) the homogeneous mixed condensation route ( 12-14, 2 1); and (3) the subphthalocyanine route (1 1). There are difficulties with all three routes for large-scale preparation of unsymmetrical alkoxy-substituted phthalocyanines.Route 1 is not suitable for large-scale preparation of unsymmetrical phthalocyanines....

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