Molecular structure and spectroscopic properties of [2,3,9,10,16,17,23,24-octakis(3-carboxyphenoxy)phthalocyaninato-κ4N](pyridine-κN)zinc(ii) pyridine octasolvate

Rei Fujishiro; Hayato Sonoyama; Yuki Ide; Shigeki Mori; Tamotsu Sugimori; Atsushi Nagai; Katsumi Yoshino; Mikio Nakamura; Takahisa Ikeue

doi:10.3987/COM-16-13608

Molecular structure and spectroscopic properties of [2,3,9,10,16,17,23,24-octakis(3-carboxyphenoxy)phthalocyaninato-κ⁴N](pyridine-κN)zinc(ii) pyridine octasolvate

Rei Fujishiro, Hayato Sonoyama, Yuki Ide, Shigeki Mori^*, Tamotsu Sugimori, Atsushi Nagai, Katsumi Yoshino, Mikio Nakamura, Takahisa Ikeue

^*Corresponding author for this work

Faculty of Liberal Arts and Sciences

Research output: Contribution to journal › Article › peer-review

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Abstract

The title complex, [2,3,9,10,16,17,23,24-octakis(3-carboxyphenoxy)-phthalocyaninato-k ⁴N](pyridine-kN)zinc(II)pyridine octasolvate abbreviated as [ZnPc(3-CO₂H)₈(Py)]'8(Py) (2), has been obtained by recrystallization of [ZnPc(3-CO₂H)₈] (1) from pyridine. Molecular structure of 2 determined by X-ray crystallography exhibits the anticipated N₅ square pyramidal coordination around zinc(II) ion, where the average Zn-N(Pc) and Zn-N(Py) bond lengths are 2.027(4) Å and 2.121(4) Å, respectively. The deviation of the zinc(II) ion from phthalocyanine N₄ plane is 0.417 Å. Eight pyridine molecules are involved in hydrogen bonding with the carboxylic acid moieties of phenoxy rings in a 1:1 Two discrete phthalocyanine molecules in a unit cell are stacked in a back-to-back fashion with an interplanar distance of 3.376 Å. Pyridine solutions of 1 exhibit well-resolved ¹H NMR, UV-Vis, and fluorescent spectra, suggesting that 1 exists pyridine ligated monomeric species.

Original language	English
Pages (from-to)	131-139
Number of pages	9
Journal	Heterocycles
Volume	94
Issue number	1
DOIs	https://doi.org/10.3987/COM-16-13608
State	Published - 2017

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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10.3987/COM-16-13608

Cite this

@article{0f33c38af51941b08753c99e986638d1,

title = "Molecular structure and spectroscopic properties of [2,3,9,10,16,17,23,24-octakis(3-carboxyphenoxy)phthalocyaninato-κ4N](pyridine-κN)zinc(ii) pyridine octasolvate",

abstract = "The title complex, [2,3,9,10,16,17,23,24-octakis(3-carboxyphenoxy)-phthalocyaninato-k 4N](pyridine-kN)zinc(II)pyridine octasolvate abbreviated as [ZnPc(3-CO2H)8(Py)]'8(Py) (2), has been obtained by recrystallization of [ZnPc(3-CO2H)8] (1) from pyridine. Molecular structure of 2 determined by X-ray crystallography exhibits the anticipated N5 square pyramidal coordination around zinc(II) ion, where the average Zn-N(Pc) and Zn-N(Py) bond lengths are 2.027(4) {\AA} and 2.121(4) {\AA}, respectively. The deviation of the zinc(II) ion from phthalocyanine N4 plane is 0.417 {\AA}. Eight pyridine molecules are involved in hydrogen bonding with the carboxylic acid moieties of phenoxy rings in a 1:1 Two discrete phthalocyanine molecules in a unit cell are stacked in a back-to-back fashion with an interplanar distance of 3.376 {\AA}. Pyridine solutions of 1 exhibit well-resolved 1H NMR, UV-Vis, and fluorescent spectra, suggesting that 1 exists pyridine ligated monomeric species.",

author = "Rei Fujishiro and Hayato Sonoyama and Yuki Ide and Shigeki Mori and Tamotsu Sugimori and Atsushi Nagai and Katsumi Yoshino and Mikio Nakamura and Takahisa Ikeue",

note = "Publisher Copyright: {\textcopyright} 2017 The Japan Institute of Heterocyclic Chemistry.",

year = "2017",

doi = "10.3987/COM-16-13608",

language = "英語",

volume = "94",

pages = "131--139",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "1",

}

TY - JOUR

T1 - Molecular structure and spectroscopic properties of [2,3,9,10,16,17,23,24-octakis(3-carboxyphenoxy)phthalocyaninato-κ4N](pyridine-κN)zinc(ii) pyridine octasolvate

AU - Fujishiro, Rei

AU - Sonoyama, Hayato

AU - Ide, Yuki

AU - Mori, Shigeki

AU - Sugimori, Tamotsu

AU - Nagai, Atsushi

AU - Yoshino, Katsumi

AU - Nakamura, Mikio

AU - Ikeue, Takahisa

PY - 2017

Y1 - 2017

N2 - The title complex, [2,3,9,10,16,17,23,24-octakis(3-carboxyphenoxy)-phthalocyaninato-k 4N](pyridine-kN)zinc(II)pyridine octasolvate abbreviated as [ZnPc(3-CO2H)8(Py)]'8(Py) (2), has been obtained by recrystallization of [ZnPc(3-CO2H)8] (1) from pyridine. Molecular structure of 2 determined by X-ray crystallography exhibits the anticipated N5 square pyramidal coordination around zinc(II) ion, where the average Zn-N(Pc) and Zn-N(Py) bond lengths are 2.027(4) Å and 2.121(4) Å, respectively. The deviation of the zinc(II) ion from phthalocyanine N4 plane is 0.417 Å. Eight pyridine molecules are involved in hydrogen bonding with the carboxylic acid moieties of phenoxy rings in a 1:1 Two discrete phthalocyanine molecules in a unit cell are stacked in a back-to-back fashion with an interplanar distance of 3.376 Å. Pyridine solutions of 1 exhibit well-resolved 1H NMR, UV-Vis, and fluorescent spectra, suggesting that 1 exists pyridine ligated monomeric species.

AB - The title complex, [2,3,9,10,16,17,23,24-octakis(3-carboxyphenoxy)-phthalocyaninato-k 4N](pyridine-kN)zinc(II)pyridine octasolvate abbreviated as [ZnPc(3-CO2H)8(Py)]'8(Py) (2), has been obtained by recrystallization of [ZnPc(3-CO2H)8] (1) from pyridine. Molecular structure of 2 determined by X-ray crystallography exhibits the anticipated N5 square pyramidal coordination around zinc(II) ion, where the average Zn-N(Pc) and Zn-N(Py) bond lengths are 2.027(4) Å and 2.121(4) Å, respectively. The deviation of the zinc(II) ion from phthalocyanine N4 plane is 0.417 Å. Eight pyridine molecules are involved in hydrogen bonding with the carboxylic acid moieties of phenoxy rings in a 1:1 Two discrete phthalocyanine molecules in a unit cell are stacked in a back-to-back fashion with an interplanar distance of 3.376 Å. Pyridine solutions of 1 exhibit well-resolved 1H NMR, UV-Vis, and fluorescent spectra, suggesting that 1 exists pyridine ligated monomeric species.

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U2 - 10.3987/COM-16-13608

DO - 10.3987/COM-16-13608

M3 - 学術論文

AN - SCOPUS:85013306246

SN - 0385-5414

VL - 94

SP - 131

EP - 139

JO - Heterocycles

JF - Heterocycles

IS - 1