Phthalocyanines Containing Silicons in Their Peripheral Substituent Groups

Kobayashi, Nagao; Higashi, Ryuji; Tomura, Tatsuya

doi:10.1246/bcsj.70.2693

Cited by 17 publications

(10 citation statements)

References 6 publications

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“…Although aryl substituents in 1,4 59 The available X-ray crystal structures of these complexes clearly suggest a highly distorted phthalocyanine core, which leads to a tremendous red-shift of the Qband in UV-vis spectra. Of course, increase of steric hindrance by phenyl substituents compared to the more conformationally flexible alkyl groups results in very low yields of the target compounds.…”

Section: Methodsmentioning

confidence: 98%

Synthesis of substituted phthalocyanines

Nemykin¹,

Luk’yanets²

2010

Arkivoc

151

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This review summarizes the synthetic strategies for substituted phthalonitriles and phthalocyanines. Preparation of alkyl-, aryl-, halo-, nitro-, alkoxy-, aryloxy-, alkylthio-, arylthio-, and amino-substituted phthalocyanines along with the derivatives of phthalocyanine carboxylicand sulfoacids is overviewed. Influence of the substituents on the position of Q-band in UV-vis spectra of substituted phthalocyanines is also briefly discussed.

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Section: Methodsmentioning

confidence: 98%

Synthesis of substituted phthalocyanines

Nemykin¹,

Luk’yanets²

2010

Arkivoc

151

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“…This situation appears to be occurring in the films of Pcs 1 and 2, since they have two bulky substituents as axial ligands. In addition, the Q bands in the thin films are sharper than those seen for other phthalocyanines [19,20], implying that these compounds are monomeric even in the solid phases. A new, somewhat surprising finding in this study is that even 2, which has two long non-branched chains, had the Q band at longer wavelength than in solution.…”

Section: Electronic Absorption Spectramentioning

confidence: 78%

“…It is known that the Q bands of Pcs which have peripheral substituents at the carbons furthest from the Pc core generally appear at shorter wavelengths than those in solution, while those which have peripheral substituents at the carbons closest to the Pc core appear at longer wavelengths [19]. These shifts of the Q band positions in the films from those in solution have been explained by the differences in aggregation, and the longer-wavelength shift has been ascribed to an absence of face-to-face-type stacking of the Pc planes.…”

Section: Electronic Absorption Spectramentioning

confidence: 99%

Synthesis and some spectroscopic properties of tetra-2,3-pyridoporphyrazinatosilicon involving bulky axial ligands

Nonomura

Kobayashi

Tomura

2000

J. Porphyrins Phthalocyanines

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Tetra-2,3-pyridoporphyrazinatosilicon ( SiPyD ) containing bis(tri-n-hexylsiloxy) (1) or bis(n-heptylcarbonyloxy) (2) axial ligands have been prepared and characterized by NMR, IR and electronic absorption spectroscopies and by thermogravimetric analysis (TGA) and differential thermal analysis (DTA). These SiPyDs are soluble in common organic solvents, and face-to-face-type stacking is prevented in solution and films. Accordingly, their NMR spectra could be reasonably assigned. Their electronic absorption spectra in solution appear to the blue and red compared with those of the corresponding Si phthalocyanines ( SiPcs ) and Si tetrapyrazinoporphyrazines ( SiPyZs ) respectively. These characteristics are reproduced by molecular orbital calculations in the framework of the Pariser-Parr-Pople approximation. On formation of films, the Q bands shift to the red of those in solution by ca 20 nm, suggesting that other similar tetravalent metallophthalocyanines with two long axial ligands can be used for shifting the Q band to the red. TGA and DTA experiments show that the thermal stability of the macrocycles is markedly influenced by the type of axial ligands.

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“…In Figure B, the absorption spectra of 1 in chloroform and in the form of a film are being compared. For phthalocyanines, upon film formation, it is known that the Q-bands of Pcs with alkyl or alkoxy groups attached to the benzene carbons furthest from the Pc core lie to the blue compared to the same Pcs in solutions, while Pcs with eight alkoxy groups closest to the Pc have a Q-band shifted to the red . For phthalocyanines, this information has been important in designing applications, for example, for optical disks.…”

Section: Resultsmentioning

confidence: 99%

An Adjacent Dibenzotetraazaporphyrin: A Structural Intermediate between Tetraazaporphyrin and Phthalocyanine

et al. 1999

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An adjacent dibenzotetraazaporphyrin, in which two benzene units are fused to the adjacent pyrrole rings of tetraazaporphyrin skeleton, has been synthesized as a copper complex for the first time and characterized by electronic absorption and magnetic circular dichroism spectroscopy, by cyclic voltammetry and spectroelectrochemistry using an optically transparent thin layer electrochemical cell. The results were compared with those of tetraazaporphyrin and phthalocyanine analogues. The title compound shows intermediate characteristics between those of normal tetraazaporphyrins and phthalocyanines; the Q-band shifts to the red and becomes more intense while the Soret band broadens with increasing the size of the pi-system. With the expansion of the pi-system, the first reduction potential does not change significantly, while the first oxidation potential shifts negatively, indicating that the LUMO level remains almost constant while the HOMO level destabilizes significantly. These spectroscopic properties and redox potentials were reproduced by molecular orbital calculations within the framework of the Pariser-Parr-Pople approximation. Thermogravimetry analysis suggests that the skeleton of the adjacent dibenzotetraazaporphyrin complex decomposes at about 95 degrees lower than that of the tetra-tert-butylated phthalocyanine analogue.

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Phthalocyanines Containing Silicons in Their Peripheral Substituent Groups

Cited by 17 publications

References 6 publications

Synthesis of substituted phthalocyanines

Synthesis of substituted phthalocyanines

Synthesis and some spectroscopic properties of tetra-2,3-pyridoporphyrazinatosilicon involving bulky axial ligands

An Adjacent Dibenzotetraazaporphyrin: A Structural Intermediate between Tetraazaporphyrin and Phthalocyanine

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