Triazolephthalocyanines: synthesis, supramolecular organization and physical properties

Nicolau, Mónica; Cabezón, Beatriz; Torres, Tomás

doi:10.1016/s0010-8545(99)00068-5

Cited by 47 publications

(32 citation statements)

References 25 publications

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“…[9] These intrinsically unsymmetrical compounds, reported for the first time by us in 1994, [10] are aromatic phthalocyanine analogues in which one isoindole moiety has formally been replaced by a 1,2,4-triazole subunit. The introduction of this heterocycle into the phthalocyanine framework gives rise to a lower degree of electronic delocalization, which results in a hypsochromic character.…”

Section: Introductionmentioning

confidence: 99%

Triazoleporphyrazines: A New Class of Intrinsically Unsymmetrical Azaporphyrins

2002

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Triazoleporphyrazine 5 has been prepared by means of a ''3+1'' crossover condensation of the pyrroline derivative 6 with 3,5-diamino-1,2,4-triazole. Metallation of 5 under standard conditions afforded the metallotriazoleporphyrazines 7.In contrast with the porphyrinic nature observed for its triazoleporphyrin counterpart 3, the free base triazoleporphyrazine 5 possessed a cross-conjugated, hemiporphyrazine-like

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Section: Introductionmentioning

confidence: 99%

Triazoleporphyrazines: A New Class of Intrinsically Unsymmetrical Azaporphyrins

2002

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“…Many varieties of building blocks have been utilized; the most common types are amphiphilic molecules, e.g. carbohydrates, and rod-and disk-like molecules such as biphenyls, triphenylenes, porphyrins, phthalocyanines and, more recently, even larger flat molecules [4][5][6][7][8][9][10][11][12]. Traditionally, covalent synthesis was used to link the molecular units forming the molecular materials.…”

Section: Introductionmentioning

confidence: 99%

Molecular materials based on crown ether functionalized phthalocyanines

Engelkamp

Nolte

2000

J. Porphyrins Phthalocyanines

205

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This micro-review presents an overview of molecular materials derived from phthalocyanines which are substituted with crown ether rings. These flat disk-like molecules can self-assemble into ordered, well-defined structures with or without the aid of alkali metal ions. Highly ordered assemblies of crown ether phthalocyanines are capable of transporting electrons and ions, which is of interest for sensor applications.

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“…5 ϫ 10 Ϫ5 ) shows two strong absorption Scheme 5 Scheme 6 bands in the near UV region at 260 and 370 nm, together with several weaker absorptions in the UV/Vis region at 525, 570, and 625 nm (Q-band). [14] The addition of potassium acetate to the solution of 24 mentioned above gives rise to notable changes in the UV/Vis spectrum. Spectra were taken at three different molar ratios of macrocycle/ salt, namely 1:0.5, 1:1 and 1:10.…”

Section: Resultsmentioning

confidence: 99%

“…[10Ϫ12] Another approach, which is less developed, involves the preparation of noncentrosymmetrical phthalocyanine analogues, formally obtained by the substitution of one isoindole subunit in a phthalocyanine by another conjugated heterocyclic moiety. [4,13] As a consequence of our interest in the synthesis of noncentrosymmetrical phthalocyanines with high second-order nonlinear optical responses, we prepared, for the first time, the so-called ''triazolephthalocyanine'' (Tpc), [14] a phthalocyanine analogue in which one 1,2,4-triazole subunit has formally replaced an isoindole subunit of the phthalocyanine core. These unsymmetrical macrocycles display important second-and third-order nonlinear optical properties in solution, [15] and high thermal stability, [16] similar and even higher to those shown by phthalocyanines.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Crowned Triazolephthalocyanines

et al. 2000

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The synthesis of triazolephthalocyanines bearing crown ether and aza‐crown ether substituents is described. Different substituents have been introduced on the nitrogen atom of the aza‐crown moiety to improve the solubility and the intrinsic amphiphilic character of these macrocycles. The crowned triazolephthalocyanines described have been prepared by a statistical procedure, and also by different variations of a stepwise method. Preliminary studies of the aggregation properties of one representative of this new family of compounds have also been carried out. An exhaustive study of the synthesis of the corresponding dicyano derivative precursors of the triazolephthalocyanines is displayed. Two different approaches have been used for this goal: The first one inserts the cyano groups prior to the synthesis of the crown ether moiety, while the second one builds the crown ether part of the molecule in advance of the cyanation process. The incompatibility of the Rosemund‐von‐Braun cyanation conditions and the presence of nitrogen atoms in the molecule is the main difficulty of the synthesis of these precursors.

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Triazolephthalocyanines: synthesis, supramolecular organization and physical properties

Cited by 47 publications

References 25 publications

Triazoleporphyrazines: A New Class of Intrinsically Unsymmetrical Azaporphyrins

Triazoleporphyrazines: A New Class of Intrinsically Unsymmetrical Azaporphyrins

Molecular materials based on crown ether functionalized phthalocyanines

Synthesis of Crowned Triazolephthalocyanines

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