Structure of tetra-n-propylporphine. Average structure for the free base macrocycle from three independent determinations

Codding, Penelope W.; Tulinsky, A.

doi:10.1021/ja00767a016

Cited by 61 publications

(22 citation statements)

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“…In these the center-methine carbon atom distances are 3.448 and 3-392 A, respectively. Similarly in the recent determination of the structure of the free base of octaethylporphyrin (Lauher & Ibers, 1973) the center-methine carbon atom distance is 3.42 .~, while in various meso-substituted free base porphyrins this distance varies from 3.44-3.45/~ (Codding & Tulinsky, 1972;Silvers & Tulinsky, 1967). In the tetragonal form of tetraphenylporphyrin (Hamor, Hamor & Hoard, 1964) this distance is the same as in octaethylporphyrin and as in porphine itself (Chen & Tulinsky, 1972).…”

Section: Determination and Refinement Of The Structurementioning

confidence: 81%

Crystal and molecular structure of 1,2,3,4,5,6,7,8-octaethylporphinatodichlorotin(IV) nitromethane solvate

Cullen¹,

Meyer²

1973

Acta Crystallogr Sect B

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2507of the ThzNilv-type structure decreases. This suggests that the degree of order of the ThzNi17-type structures of Pr2C017 and NdzC017 is lowest. Therefore, the ThzNi~v-type compounds for these R elements do not exist. The degree of order of the ThzNi~7-type structures of Ce2C0~7 and Ho2Co17 is nearly ideal. One therefore gets only traces of the ThzZnlv-type structure even after prolonged annealing at lower temperatures. Dy2C017 appears to lie in between these two extreme cases. This is the reason that both modifications i.e.ThzNit7+ThzZnlv-type, are obtained in almost equal proportions below 1200°C.Since those R elements, studied in this work are uniformly distributed throughout the whole rare-earth series, the results obtained for their AzB17 compounds can generally be applied to all the RzCox7 compounds (Fig. 1). Buschow (1966) and Givord, Givord & Lemaire (1972) have explained the polymorphism of RzCo~v in terms of the radii ratios of R and Co atoms. No doubt the atomic radii of R and Co atoms are important factors in the formation of RECO~7. However, the atomic ratio model alone cannot explain the polymorphism of R2Co17 over the rare-earth series and the degree of order of R2Co17 of the Th2Ni17-type structure.In our opinion, the valence-electron concentration and the electron-spatial correlation play a deciding role in the stabilization of one or more of the polymorphic forms of R2C0~7 for a particular R element at a particular temperature.

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Section: Determination and Refinement Of The Structurementioning

confidence: 81%

Crystal and molecular structure of 1,2,3,4,5,6,7,8-octaethylporphinatodichlorotin(IV) nitromethane solvate

Cullen¹,

Meyer²

1973

Acta Crystallogr Sect B

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“…Most instances of macrocycle distortion involve metalation and/or the presence of complex substituents requiring non-planar inter-porphyrin bonding arrangements. ; from data of [7,[12][13][14][15]. Shown without hydrogens.…”

Section: Peripheral Substituentsmentioning

confidence: 99%

“…Crystallographic data are available for several metalated porphines, of which data for four ; from data of [7,[12][13][14][15]. Shown without hydrogens.…”

Section: Metalation Of the Macrocycle Corementioning

confidence: 99%

Structural Aspects of Porphyrins for Functional Materials Applications

2017

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Porphyrinic compounds comprise a diverse group of materials which have in common the presence of one or more cyclic tetrapyrroles known as porphyrins in their molecular structures. The resulting aromaticity gives rise to the semiconducting properties that make these compounds of interest for a broad range of applications, including artificial photosynthesis, catalysis, molecular electronics, sensors, non-linear optics, and solar cells. In this brief review, the crystallographic attributes of porphyrins are emphasized. Examples are given showing how the structural orientations of the porphyrin macrocycle, and the inter-porphyrin covalent bonding present in multiporphyrins influence the semiconducting properties. Beginning with porphine, the simplest porphyrin, we discuss how the more complex structures that have been reported are described by adding peripheral substituents and internal metalation to the macrocycles. We illustrate how the conjugation of the π-bonding, and the presence of electron donor/acceptor pairs, which are the basis for the semiconducting properties, are affected by the crystallographic topology.

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“…The structure was refined by full-matrix least squares using SHELX76 (Sheldrick, 1976 The X-ray crystallographic structure determinations of some synthetic free-base porphyrins have been reported, e.g. porphine (Chen & Tulinsky, 1972), tetraphenyl porphyrin (TPP) (Silvers & Tulinsky, 1967) and tetra-n-propylporphyrin (Codding & Tulinsky, 1972). The structure determination of the title compound was undertaken to elucidate the effects of steric interactions on the bond lengths and angles concerned.…”

mentioning

confidence: 99%