Macrodiscotic triphenylenophthalocyanines

Cammidge, Andrew N.; Gopee, Hemant

doi:10.1039/b200978a

Cited by 75 publications

(36 citation statements)

References 6 publications

(7 reference statements)

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“…13 In addition, coordination of metal centers to the triphenylene core offers a versatile way to modify the properties of the system. 14,15,16,17 There are a few reports of liquid crystalline metal-organic triphenylene systems with covalently bonded Hg, 18 Cr 0 , 19 Zn II , 20 Cu II , Ni II , 21 Ag I , 22 and Pt II complexes. 23 Exploring the possibility to develop columnar materials in which columns of different natures coexist, we reported recently a family of mesomorphic mono and dinuclear ortho-metallated palladium complexes containing a columnar packing of triphenylene moieties that supports an associated stack of metal moieties.…”

Section: Introductionmentioning

confidence: 99%

Isocyano-Triphenylene Complexes of Gold, Copper, Silver, and Platinum. Coordination Features and Mesomorphic Behavior

Chico

Domínguez

Donnio

et al. 2016

Crystal Growth & Design

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Stable organometallic complexes [AuX(CN-TriPh)] [X = Cl, C6F5, C6F4O-C10H21, C6F4O-(R)-2-octyl], [(μ-4,4′-C6F4C6F4){Au(CN-TriPh)}2], [CuCl(CN-TriPh)], trans-[PtI2(CN-TriPh)2], and [Ag(CN-TriPh)2]BF4, bearing the previously unreported triphenylene-isocyanide ligand 1-isocyano-2,3,6,7,10,11-hexadodecyloxytriphenylene (CN-TriPh), have been synthesized. The coordination features of the metal ion determine their thermal behavior. The free isocyanide ligand and all of the monomeric gold derivatives display enantiotropic mesomorphic behavior over a wide range of temperature (from 5 to 220 °C), while the copper complex, with the same stoichiometry but not isostructural with the gold complexes, melts directly to an isotropic liquid. The bis-isocyanide platinum and silver complexes also melt directly to an isotropic liquid at low temperatures. In this case, the two trans coordinated isocyanide ligands, connected by a too short linker, cannot become coplanar, which prevents the formation of a mesogenic structure. On the contrary, in the dinuclear gold complex the two isocyanide trans ligands are, due to the long Au–C6F4–C6F4–Au bridge, sufficiently separated to become coplanar, and this complex gives rise to a mesophase. The structures of the mesophases were determined by small-angle X-ray scattering. All materials prepared show a fluorescent emission centered on the triphenylene core.

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Section: Introductionmentioning

confidence: 99%

Isocyano-Triphenylene Complexes of Gold, Copper, Silver, and Platinum. Coordination Features and Mesomorphic Behavior

Chico

Domínguez

Donnio

et al. 2016

Crystal Growth & Design

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“…[10] The synthesis of phthalocyanines with extended p-systems (Scheme 1) is commonly achieved by using an ortho-dicyano precursor for the cyclotetramerization reaction to the Pc. Owing to a lack of methods for the direct ortho-functionalization of polycyclic aromatic hydrocarbons (PAH), precursors were built from various benzene or naphthalene derivatives for the synthesis of phenanthralocyanine (Phc), [11] triphenylenophthalocyanine (Tc), [12] helicenocyanine (Hc), [13] benzohelicenocyanine (BHc), [14] and perylenophthalocyanine (PPc). [15] Synthetic routes to multiply benzannulated Pcs have been designed to include solubilizing alkyl chains to overcome solubility problems.…”

Section: Introductionmentioning

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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“…Very few examples of mesomorphic Zn(II) complexes reported up to now are based on dithiobenzoate [5], terpyridine [6] or 2,6-bis-[3 0 ,4 0 ,5 0 -tri(alkoxy)phenyliminomethyl]pyridines ligands [7] or on porphyrin and phtalocyanine derivatives in which the Zn(II) centre shows both a trigonal-bipyramidal geometry or a square planar geometry when incorporated in the cycle [5,8]. Only very recently two examples of Zn(II) derivatives showing the rigid tetrahedral geometry, usually considered to prevent mesophase formation [9], CHART 1 General formula of ligands H 2 (salen-n).…”

Section: Introductionmentioning

confidence: 99%

Thermotropic Mesomorphism in Salen-like Zinc Complexes

Aiello

Bellusci

Crispini

et al. 2008

Molecular Crystals and Liquid Crystals

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The reaction between a series of non mesogenic tetradentate salen-like Schiff bases and Zn(II) acetate gives rise to the formation of liquid cristalline complexes showing nematic and smectic phases stable over a quite large temperature range. A dimeric structural arrangement could favour the appearance of such type of mesophase in the case of 1,3-diaminopropane and 1,3-diamino-2,2-dimethylpropane bridges containing ligands while for the salen derivatives a monomeric solvent-induced pentacoordinated arrengement observed in solution and in the crystalline molecular structure, probably prevent the liquid crystalline behaviour.

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Macrodiscotic triphenylenophthalocyanines

Abstract: The first heavily substituted triphenylenophthalocyanines have been synthesised and found to be mesogenic.

Cited by 75 publications

References 6 publications

Isocyano-Triphenylene Complexes of Gold, Copper, Silver, and Platinum. Coordination Features and Mesomorphic Behavior

Isocyano-Triphenylene Complexes of Gold, Copper, Silver, and Platinum. Coordination Features and Mesomorphic Behavior

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

Thermotropic Mesomorphism in Salen-like Zinc Complexes

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