Preparation and characterization of (tetrabenzoporphyrinato)cobalt(II) iodide, a ring-oxidized molecular conductor

Liou, Kwangkyoung; Newcomb, Timothy P.; Heagy, Michael D.; Thompson, J.; Heuer, William B.; Musselman, Ronald L.; Jacobsen, Claus Schelde; Hoffman, Brian M.; Ibers, James A.

doi:10.1021/ic00048a015

Cited by 43 publications

(34 citation statements)

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“…Clezy's group subsequently carried out the synthesis of opp-dibenzo-and adj-dibenzoporphyrins 6a and 7 [16], respectively, and several additional studies have now been carried out on the synthesis of [14] and dibenzoporphyrins (6) [19][20][21][22][23][24][25]. In addition, numerous studies have been carried out on the synthesis of tetrabenzoporphyrins (4) [2][3][4][5][6][7][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40] and the related meso-tetraarylporphyrins (8) [25,[41][42][43][44][45][46][47][48]. The electronic absorption spectra for these systems and their metal complexes are summarized in Table 1.…”

Section: Benzoporphyrins: Structural Analogues Of the Phthalocyaninesmentioning

confidence: 99%

Modification of the porphyrin chromophore by ring fusion: identifying trends due to annelation of the porphyrin nucleus

Lash

2001

J. Porphyrins Phthalocyanines

122

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ABSTRACT:The effects exerted by fused aromatic rings on the UV-vis spectra of porphyrins are surveyed. Modified porphyrin chromophores with fused benzene, 1,2-naphthalene, 9,10-phenanthrene or phenanthroline rings are surprisingly little affected even when a maximum number of ring fusions are incorporated. Linearly annealed naphtho-or anthraporphyrins show large red shifts to the Q bands but the Soret absorptions are weakened and undergo only minor bathochromic shifts. Fluoranthoporphyrins give multiple bands in the Soret region, but the Q band region is virtually unaffected by this tetracyclic ring system. On the other hand, metal chelates of fluoranthoporphyrins show surprisingly strong bands near 600 nm. Benzothiadiazole rings split and weaken the Soret band, but the Q bands region is unexceptional. However, metal coordination again produces relatively intense bands near 600 nm. The most significant results were obtained for porphyrins with fused acenaphthylene rings. Monoacenaphthoporphyrins (41) have three Soret bands at 387, 431 and 454 nm, and the longest wavelength Q band is shifted to 658 nm. opp-Diacenaphthoporphyrin (43) further shifts these bands with two Soret absorbances at 443 and 470 nm, and an additional strong peak is observed at 692 nm. The metal complexes of these systems also show strong bands between 602 and 656 nm. Still larger effects are produced by tetraacenaphthoporphyrin (47), the dication for which in trifluoroacetic acid (TFA)-chloroform has a Soret absorption at 528 nm. Tetraaryltetraacenaphthoporphyrins (48) are even more red shifted, showing Soret bands between 556 and 570 nm for the free bases and 565 to 588 nm for the related dications. The lead(II) chelate for tetraphenylporphyrin (48a) shows an additional 'hyper' spectral shift that brings the Soret band to 604 nm, and this effect can also be achieved by introducing four meso-phenylethynyl substituents onto the tetraacenaphthoporphyrin nucleus (49). In addition, by combining these two factors for the lead(II) chelate of 49, a record-breaking value for the Soret band of 642 nm can be achieved. Spectral shifts due to ring annelation in porphyrin analogues are also discussed, including those for oxybenziporphyrins, oxypyriporphyrins, carbaporphyrins and sapphyrins.

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Section: Benzoporphyrins: Structural Analogues Of the Phthalocyaninesmentioning

confidence: 99%

Modification of the porphyrin chromophore by ring fusion: identifying trends due to annelation of the porphyrin nucleus

Lash

2001

J. Porphyrins Phthalocyanines

122

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“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] In particular, the one-dimensional conductor based on a metal phthalocyanine ͑MPc͒ are the unique double-chain system which involves two conductive pathways in the same molecular column. The phthalocyanine molecule is located on a fourfold axis in a tetragonal lattice, and these molecules are stacked with a metal-over-metal overlapping mode.…”

Section: Introductionmentioning

confidence: 99%

Pressure-induced d–π charge transfer in one-dimensional phthalocyanine conductors, NiPc(AsF6)0.5 and CoPc(AsF6)0.5

Hiejima

Yakushi

1995

The Journal of Chemical Physics

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Direct structural characterization of charge localization in metal to ligand charge transfer complexes AIP Conf.Pressure dependence of optical absorption spectra were measured for ͑phthalocyaninato͒-nickel hexafluoroarsenate, NiPc(AsF 6 ) 0.5 and ͑phthalocyaninato͒-cobalt hexafluororarsenate, CoPc(AsF 6 ) 0.5 . We found a charge transfer from the central metal ion to the macrocycle at 0.5 GPa in NiPc(AsF 6 ) 0.5 and 1.1 GPa in CoPc(AsF 6 ) 0.5 . According to the electron-filling process in the -conduction band, a metal-insulator transition and an evolution of the energy gap was observed in NiPc(AsF 6 ) 0.5 . On the other hand, nonmetallic CoPc(AsF 6 ) 0.5 showed a continuous change.

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“…The last 20 years have seen a substantial effort in exploiting the natural tendency for phthalocyanines and porphyrins to cofacially stack to create a family of materials which, when appropriately doped with weak oxidants, exhibit conductivities in the semiconductor or metallic regimes [1][2][3][4][5][6][7][8][9][10][11][12][13]. The first examples of such conductors were the iodine-doped crystalline phthalocyanines and porphyrins.…”

Section: New Electrically Conductive Organic Materialsmentioning

confidence: 99%

“…Most approaches have subsequently added side chains to the periphery of the monomeric demetallated or transition metal Pc or porphyrin, imparting in most instances liquid crystalline properties to these molecules [1][2][3][4][5][6][7][8][9][10][11][12][13]. Rational assembly of these columnar assemblies into single wires or bundles of wires with nanometer control over architecture has still not been achieved, with a few notable exceptions.…”

Section: New Electrically Conductive Organic Materialsmentioning

confidence: 99%

Phthalocyanines and porphyrins as materials

Armstrong

2000

J. Porphyrins Phthalocyanines

115

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Several recent studies of phthalocyanines and porphyrins as materials in emerging technologies are reviewed here. Emphasis is placed on the use of these materials as components in building materials where the symmetry, optical and electrical properties of the molecule are important. Aggregates or polymers of these molecules have been known for some time to possess interesting electrical conductivities, and more recently interesting optical properties. Their optical properties as isolated species in condensed phases have also recently become interesting, and their ability to form new hybrid materials, by mixing or by thin film deposition, with other molecules with different electron affinities and ionization potentials, now appears to be extremely attractive. Device technologies in which we can anticipate these molecules appearing in the near future include organic light-emitting diodes, organic field effect transisitors, organic photovoltaics, optical limiters and optically based chemical sensors.

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Preparation and characterization of (tetrabenzoporphyrinato)cobalt(II) iodide, a ring-oxidized molecular conductor

Cited by 43 publications

References 0 publications

Modification of the porphyrin chromophore by ring fusion: identifying trends due to annelation of the porphyrin nucleus

Modification of the porphyrin chromophore by ring fusion: identifying trends due to annelation of the porphyrin nucleus

Pressure-induced d–π charge transfer in one-dimensional phthalocyanine conductors, NiPc(AsF6)0.5 and CoPc(AsF6)0.5

Phthalocyanines and porphyrins as materials

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