Discotic liquid crystals of transition metal complexes X. Phthalocyanine derivatives substituted with<i>n</i>-alkyloxyphenyl side chains

Ohta, Kazuchika; Watanabe, Takuya; Tanak, Satoshi; Fujimoto, Testsuya; Yamamoto, Iwao; Bassoul, P.; Kucharczyk, Nathalie; Simon, Jacques

doi:10.1080/02678299108026282

Cited by 35 publications

(13 citation statements)

References 13 publications

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“…[16,17] A recent communication described an elegant route to aryl-disubstituted phthalonitriles through reactions between commercially available 4,5-dichlorophthalonitrile and arylboronic acids, and the prepared phthalonitriles underwent cyclotetramerization to give the corresponding phthalocyanines.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Some Properties of Aryl‐ and Aryloxy‐Substituted Phthalocyanines and Their Metal Complexes: A Comparison with Porphyrazine and Naphthalocyanine Analogues

Vagin

Hanack

2004

Eur J Org Chem

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The preparation of new octakis [m-(trifluoromethyl)phenyl]-and octakis [m-(trifluoromethyl)phenoxy]phthalocyanines (6a and 6b) and their complexes with magnesium (5a, 5b) and indium (7a, 7b) is described. Their spectroscopic properties and solubilities are discussed in relation to those of metalfree and metallated octakis[m-(trifluoromethyl)phenyl]porphyrazine, as well as those of metal m-(trifluoromethyl)-phenyl-and m-(trifluoromethyl)phenoxy-substituted 2,3-naphthalocyanines. A drastic decrease in the solubilities of

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Section: Methodsmentioning

confidence: 99%

Synthesis and Some Properties of Aryl‐ and Aryloxy‐Substituted Phthalocyanines and Their Metal Complexes: A Comparison with Porphyrazine and Naphthalocyanine Analogues

Vagin

Hanack

2004

Eur J Org Chem

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“…at 402 o C. The twostep decomposition has already found in the other liquid crystals based on phthalocyanine derivatives and studied in detail. 22 In this paper, the 1 st decomp. was indicated from the absorption 20 spectra that two neighbouring phenyl groups may form a ring by intramolecular ring-closing reaction with losing two hydrogen atoms, which is, therefore, accompanied by almost no weight loss.…”

Section: Phase Transition Behaviourmentioning

confidence: 99%

Flying-seed-like liquid crystals. Part 4: a novel series of bulky substituents inducing mesomorphism instead of using long alkyl chains

2015

Self Cite

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We have synthesized a novel series of flying-seed-like derivatives (3a~g) based on phthalocyaninato copper(II) (abbreviated as PcCu) substituted by bulky groups {PhO (a), Thus, we have revealed that mesomorphism could be induced by these novel bulky substituents instead of using long alkyl chains, and that the mesophase structures were greatly affected by the number and position of methoxy groups. Especially, it is very interesting that the derivatives having methoxy group(s) at the meta position(s), 3c, 3e, 3f and 3g, tend to show enantiotropic mesophase(s), whereas neither the derivative having no methoxy group, 3a, nor the derivative having a methoxy group at the para position, 20 3d, show a mesophase.

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“…The effect of the metal on the thermal properties of Pcs has been frequently reported in literature, [37] but little is known about its influence on molecular packing. There are only few studies on the relationship between molecular packing and the central metal for columnar liquid crystals.…”

Section: D Waxs Investigationmentioning

confidence: 99%

4,5‐Pyrenocyanine—Just Another Phthalocyanine? A STM and 2D WAXS Study

Zöphel

Mali

Puniredd

et al. 2012

Chemistry A European J

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Pyrene-fused tetraazaporphyrins were synthesized from pyrene-4,5-dicarbonitrile precursors using a recently reported procedure as the key step for the asymmetric substitution of pyrene. Metal-free, zinc- and lead-centered pyrenocyanines were obtained and their optical properties as well as their molecular assembly in the solution and bulk phases and at the liquid/solid interface were studied. The characteristic Q-band appears broadened, most likely owing to distortion of the molecule introduced by the steric demand of the angularly extended aromatic residue. The angular annulation does not bathochromically shift the Q-band as far as would have been expected for the linear case. Peripheral substitution with linear and branched alkoxy chains affords solubility of the compounds in organic solvents. The influence of the distinct steric demand of the substituents on aggregation was investigated for metal-centered pyrenocyanines by using temperature-dependent (1)H NMR and UV/Vis spectroscopy. The self-assembly at the liquid/solid interface was studied using scanning tunneling microscopy. The alkoxy substituents facilitate the anchoring of these slightly non-planar molecules on the surface of graphite. Pyrenocyanine molecules form well-ordered 2D arrays in which the molecules are arranged in rows. The angular annulation of the pyrenocyanine residue leads to characteristic adsorption behavior at the liquid/solid interface, in which the molecules adsorb in two different adsorption geometries. The alkoxy side-chains give rise to a discotic columnar superstructure and induce distinct thermotropic behavior. Dependent on the steric demand of the branched chains and the central metal atom, the molecules are rotated with respect to each other to form helical organization.

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Discotic liquid crystals of transition metal complexes X. Phthalocyanine derivatives substituted withn-alkyloxyphenyl side chains

Cited by 35 publications

References 13 publications

Synthesis and Some Properties of Aryl‐ and Aryloxy‐Substituted Phthalocyanines and Their Metal Complexes: A Comparison with Porphyrazine and Naphthalocyanine Analogues

Synthesis and Some Properties of Aryl‐ and Aryloxy‐Substituted Phthalocyanines and Their Metal Complexes: A Comparison with Porphyrazine and Naphthalocyanine Analogues

Flying-seed-like liquid crystals. Part 4: a novel series of bulky substituents inducing mesomorphism instead of using long alkyl chains

4,5‐Pyrenocyanine—Just Another Phthalocyanine? A STM and 2D WAXS Study

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