Light-induced dioxygen reduction at thin film electrodes of various porphyrins

Schlettwein, Derck; Kaneko, Masao; Yamada, Atsuo; Woehrle, D.; Jaeger, N. I.

doi:10.1021/j100157a049

Cited by 123 publications

(52 citation statements)

References 5 publications

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“…The potential use of aza analogs of phthalocyanine (AzaPc) and naphthalocyanine (AzaNc) as electrocatalysts for oxygen reduction (1,2), materials for electrochromic displays (3)(4)(5), media for optical data storage with a large-capacity memory (6)(7)(8), and photosensitizers for photodynamic therapy of cancer (9, 10) has been extensively investigated in the past decade. We previously reported on the synthesis and properties of an AzaPc series differing in the number and position of nitrogen atoms in the macrocycle, as well as in the number of attached linearly condensed benzo rings.…”

Section: Methodsmentioning

confidence: 99%

Substituted tetra-2,3-pyrazinoporphyrazines. Part I. Angular annelation of tetra-2,3-quinoxalinoporphyrazine

Kudrevich¹,

Lier²,

Gal'pern³

et al. 1996

Can. J. Chem.

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Several derivatives of 2,3-dicyanopyrazine were prepared via the condensation of o-quinones with diaminomaleodinitrile. BenzoV]quinoxaline-2,3-dinitrile was obtained from 1,2-naphthoquinone, and a series of isomeric, ditert-butyl substituted 5,6-(9,lO-phenanthro)-2.3-dicyanopyrazines were prepared from the corresponding di-tert-butyl-9,lOphenanthrenequinones. Complexation of benzov]quinoxaline-2.3-dinitrile, and unsubstituted 5,6-(9,lO-phenanthr0)-2,3-dicyanopyrazine, with an appropriate metal salt yielded metal complexes of tetra-2,3-(benzov]quinoxalino)porphyrazine and tetra-2.3-[5,6-(9.10-phenanthro)]porphyrazine, respectively. Metal-free tetra-2,3-[5,6-(9,lO-phenanthro)porphyrazine was obtained from the dilithium derivative by demetallation in HCI. These compounds have limited solubility in organic solvents, such as quinoline, and are aggregated in solutions. To eliminate the aggregation phenomenon and to determine the spectral properties of angularly annelated naphthalocyanine aza analogs, we prepared several isomeric tetra-2.3-[5,6-(di-tert-butyl-9,lOphenanthro)pyrazino]porphyrazines. These octa(tert-butyl) substituted complexes were synthesized via complexation of di-tertbutyl substituted 5,6-(9,lO-phenanthro)-2,3-dicyanopyrazines with metal salts in the presence of urea, quinoline, and tri(nbutyl)amine, and purified by silica gel chromatography. They are soluble in chloroform and substantially monomerized in solutions. A hypsochromic shift of the Q-band of octaaza naphthalocyanines versus their carbocyclic analogs was observed for all aza analogs, with the extent of the shift depending on the composition of the aromatic macrocycle. Thus, the first angularly annelated benzo ring addition causes a hypsochromic shift (-25 nm) of the Q-band of tetra-2,3-quinoxalinoporphyrazine, whereas addition of a second condensed benzo ring has little effect.Key words: phthalocyanine, aza analog, tetra-2,3-quinoxalinoporphyrazine, angular annelation.RCsurnC : Plusieurs derives de 2,3-dicyanopyrazine ont CtC prCparCs via la condensation de o-quinones avec le diaminomaleodinitrile. Le benzov]quinoxaline-2,3-dinitrile a Ct C obtenu de la 1,2-naphthoquinone et plusieurs isomkres de ditert-butyl-5,6-(9,1O-phenanthro)-2,3-dicyanopyrazines ont Ct C preparks B partir des di-tert-butyl-9,lO-phenanthrenequinones correspondants. La condensation de benzo(jquinoxaline-2,3-dinitrile et de 5,6-(9,lO-phenanthr0)-2,3-dicyanopyrazine non substituC avec un sel du metal appropriC a produit des complexes mCtalliques de tetra-2,3-(benzov]quinoxalino)porphyrazine et de tetra-2,3-[5,6-(9.10-phenanthrolporphyrazine, respectivement. La tetra-2,3-[5,6-(9,lO-phenanthro)porphyrazine sans mCtal a CtC obtenu du dCrivC de dilithium par la dCmCtallisation dans HCI. Ces composCs ont une solubilitC limitCe dans les solvants organiques tels que la quinoline et sont agrCgCs dans les solutions. Afin d'iliminer le phCnomene d'agrkgation et pour dCterminer les propriCtes spectrales des azaanalogues de naphthalocyanine avec d'anneaux angulaires condens...

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Section: Methodsmentioning

confidence: 99%

Substituted tetra-2,3-pyrazinoporphyrazines. Part I. Angular annelation of tetra-2,3-quinoxalinoporphyrazine

Kudrevich¹,

Lier²,

Gal'pern³

et al. 1996

Can. J. Chem.

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“…Porphyrin-Type Compound [157,158] Conducting glass ITO was cut into plates of 1 61.5 cm 2 and cleaned with distilled water and methanol. Macrocyclic compounds 1, 2 or 3 (R = H, M = Zn(II)) and different polymers (see above) were used.…”

Section: Preparation Of Polymer Films With An Incorporatedmentioning

confidence: 99%

Phthalocyanines in Macromolecular Phases - Methods of Synthesis and Properties of the Materials

Wöhrle¹

2001

Macromol. Rapid Commun.

108

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Phthalocyanines (Pc) and related macrocycles in combination with organic or inorganic macromolecules are reviewed. From the structural point of view, the macrocyclic compounds in macromolecular phases are subdivided into five types. Syntheses are described in detail, and characteristic experimental procedures are given. The properties of the materials are discussed: conductivity and photoconductivity, electrical charge/discharge, electrocatalytic reductions, photocatalytic reductions/oxidations of and at thin film electrodes, catalytic and photocatalytic oxidations, photoinduced electron transfer.

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“…[8][9][10][11] Ultraviolet photoelectron spectroscopy 12 and electrochemical 11,[13][14][15] studies show that porphyrin films can often be regarded as p-type semiconductors. Despite numerous studies focusing on this issue, 13,16 -27 hole transport in molecular thin films is not well understood.…”

Section: Introductionmentioning

confidence: 99%

Hole transport in porphyrin thin films

Savenije

Goossens

2001

Phys. Rev. B

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Hole transport in p-type organic semiconductors is a key issue in the development of organic electronic devices. Here the diffusion of holes in porphyrin thin films is investigated. Smooth anatase TiO 2 films are coated with an amorphous thin film of zinc-tetra͑4-carboxyphenyl͒ porphyrin ͑ZnTCPP͒ molecules acting as sensitizer. Optical excitation of the porphyrin stimulates the injection of electrons into the conduction band of TiO 2 . The remaining holes migrate towards the back electrode where they are collected. Current-voltage and capacitance-voltage analysis reveal that the TiO 2 / ZnTCPP system can be regarded as an n-p heterojunction, with a donor density of N D ϭ2.

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Light-induced dioxygen reduction at thin film electrodes of various porphyrins

Cited by 123 publications

References 5 publications

Substituted tetra-2,3-pyrazinoporphyrazines. Part I. Angular annelation of tetra-2,3-quinoxalinoporphyrazine

Substituted tetra-2,3-pyrazinoporphyrazines. Part I. Angular annelation of tetra-2,3-quinoxalinoporphyrazine

Phthalocyanines in Macromolecular Phases - Methods of Synthesis and Properties of the Materials

Hole transport in porphyrin thin films

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