Unit cell parameters for a new crystalline polymorph of lead phthalocyanine and for two polymorphs of magnesium phthalocyanine

Bluhm, Terry L.; Wagner, Hans J.; Loutfy, Rafik O.

doi:10.1007/bf00725438

Cited by 11 publications

(3 citation statements)

References 3 publications

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“…There are also series of cationic and anionic polymethines that do not contain any heteroatom in the end group. 28 The more recently described deeply colored vinylogous (cyclopentadienyl)-pentafulvenes56® and (tropylium)heptafulvenes565 belong to them.…”

Section: E Infrared Photographymentioning

confidence: 99%

Near-infrared absorbing dyes

Fabian¹,

Nakazumi²,

Matsuoka³

1992

Chem. Rev.

922

530

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Section: E Infrared Photographymentioning

confidence: 99%

Near-infrared absorbing dyes

Fabian¹,

Nakazumi²,

Matsuoka³

1992

Chem. Rev.

922

530

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“…Among the various metal elements in the periodic table, lead has been relatively little studied for complexation with phthalocyanines in either experiments or theoretic calculations despite the potential uses of these complexes as nonlinear optical materials. Studies have been mainly focused on the unsubstituted analogues, − whereas only a few substituted phthalocyaninato lead(II) complexes have been reported so far. , Herein we describe the molecular structures, molecular orbital energy gaps, atomic charges, IR and Raman spectra, and the UV−vis electronic absorption spectra of two lead complexes of phthalocyanines tetrasubstituted at the nonperipheral positions in comparison with those of unsubstituted phthalocyanine analogue with the help of DFT calculations.…”

Section: Introductionmentioning

confidence: 99%

Structures and Properties of 1,8,15,22-Tetrasubstituted Phthalocyaninato-Lead Complexes: The Substitutional Effect Study Based on Density Functional Theory Calculations

Zhang

Liu

et al. 2005

J. Phys. Chem. A

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Density functional theory (DFT) and time-dependent DFT calculations were carried out to comparatively describe the molecular structures, molecular orbital energy gaps, atomic charges, infrared (IR) and Raman spectra, and UV-vis spectra of PbPc (1), PbPc(alpha-OC2H5)4 (2), and PbPc(alpha-OC5H11)4 (3) {Pc2- = dianion of phthalocyanine; [Pc(alpha-OC2H5)4]2- = dianion of 1,8,15,22-tetra-ethoxyphthalocyanine; [Pc(alpha-OC5H11)4]2- = dianion of 1,8,15,22-tetrakis(3-pentyloxy)phthalocyanine}. The calculated structural data of compounds 1 and 3 and the simulated IR and UV-vis spectra of 3 are compared with X-ray crystallography molecular structures and the experimental absorption spectra respectively to verify the performance of the B3LYP method and the LANL2DZ basis set. Substitution of bulky alkoxy groups at the nonperipheral positions of the phthalocyanine ring adds obvious effect to the molecular structure of phthalocyaninato lead compounds by deflecting the isoindole units in the direction that the isoindole units extends and distorting them in the C4 axis direction due to the steric hindrance. Both the calculated IR and UV-vis absorption spectra of 3 correspond well with the experimental results.

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“…Among the various metal elements in the periodic table, lead has been relatively little studied for complexation with phthalocyanines despite the potential use of these complexes as nonlinear optical materials. Studies have been mainly focused on the unsubstituted analogues, − while only a few substituted (phthalocyaninato)lead(II) complexes have been reported so far . We describe herein the synthesis and characterization of three lead phthalocyanines tetrasubstituted on the nonperipheral positions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure, Spectroscopic Properties, and Electrochemistry of (1,8,15,22-Tetrasubstituted phthalocyaninato)lead Complexes

Bian

Dou

et al. 2004

Inorg. Chem.

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Three (1,8,15,22-tetrasubstituted phthalocyaninato)lead complexes Pb[Pc(alpha-OR)(4)] [H(2)Pc(alpha-OC(5)H(11))(4) = 1,8,15,22-tetrakis(3-pentyloxy)phthalocyanine; H(2)Pc(alpha-OC(7)H(15))(4) = 1,8,15,22-tetrakis(2,4-dimethyl-3-pentyloxy)phthalocyanine; H(2)Pc(alpha-OC(10)H(7))(4) = 1,8,15,22-tetrakis(2-naphthyloxy)phthalocyanine] (1-3) have been prepared as racemic mixtures by treating the corresponding metal-free phthalocyanines H(2)Pc(alpha-OR)(4) (4-6) with Pb(OAc)(2).3H(2)O in refluxing n-pentanol. The molecular structure of Pb[Pc(alpha-OC(5)H(11))(4)] (1) in the solid state has been determined by single-crystal X-ray diffraction analysis. This compound, having a nonplanar structure, crystallizes in the monoclinic system with a P2(1)/c space group. Each unit cell contains two pairs of enantiomeric molecules, which are linked by weak coordination of the Pb atom of one molecule with an aza nitrogen atom and its neighboring oxygen atom from the alkoxy substituent of another molecule, forming a pseudo-double-decker supramolecular structure in the crystals with a short ring-to-ring separation, 2.726 A, and thus a strong ring-ring pi-pi interaction. The decreased molecular symmetry for these complexes has also been revealed by the NMR spectra of 1 and 2. The methyl protons of the 3-pentyloxy and 2,4-dimethyl-3-pentyloxy side chains of 1 and 2, respectively, are chemically inequivalent. In addition to the elemental analysis and various spectroscopic characterizations, these compounds have also been electrochemically studied. Two one-electron oxidations and up to five one-electron reductions have been revealed by cyclic voltammetry (CV) and differential pulse voltammetry (DPV) methods.

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Unit cell parameters for a new crystalline polymorph of lead phthalocyanine and for two polymorphs of magnesium phthalocyanine

Cited by 11 publications

References 3 publications

Near-infrared absorbing dyes

Near-infrared absorbing dyes

Structures and Properties of 1,8,15,22-Tetrasubstituted Phthalocyaninato-Lead Complexes: The Substitutional Effect Study Based on Density Functional Theory Calculations

Synthesis, Structure, Spectroscopic Properties, and Electrochemistry of (1,8,15,22-Tetrasubstituted phthalocyaninato)lead Complexes

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