Gold(II) phthalocyanine revisited: Synthesis and spectroscopic properties of gold(III) phthalocyanine and an unprecedented ring-contracted phthalocyanine analogue

Edwin W.Y. Wong, Akito Miura, Mathew D. Wright, Qi He, Charles J. Walsby, Soji Shimizu, Nagao Kobayashi, Daniel B. Leznoff

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

In 1965, gold(II) phthalocyanine (AuPc, 1) was described to be synthesized from unsubstituted 1,3-diiminoisoindoline and gold powder or AuBr. Compound 1 has been regarded as a rare example of a paramagnetic gold(II) complex. However, its chemistry, especially the oxidation state of the central gold ion, has not been previously explored due to the inherent insolubility of 1 caused by its unsubstituted structure. In our attempt to synthesize soluble AuPcs by using 5,6-di-substituted 1,3-diiminoisoindolines, gold(III) phthalocyanine chloride (3) and a gold(III) complex of an unprecedented ring-contracted phthalocyanine analogue ([18]tribenzo-pentaaza-triphyrin(4,1,1), 4) were isolated. With this discrepant result from the original literature in hand, a reinvestigation of the original AuPc synthesis by using unsubstituted 1,3-diiminoisoindoline and various gold salts (including gold powder and AuBr) was performed, finding that only unsubstituted analogues of 3 and 4 or free-base phthalocyanine were obtained.

Original languageEnglish
Pages (from-to)12404-12410
Number of pages7
JournalChemistry - A European Journal
Volume18
Issue number39
DOIs
Publication statusPublished - Sep 24 2012

Fingerprint

Gold
Powders
phthalocyanine
Chlorides
Solubility
Salts
Ions
Oxidation

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

Gold(II) phthalocyanine revisited : Synthesis and spectroscopic properties of gold(III) phthalocyanine and an unprecedented ring-contracted phthalocyanine analogue. / Wong, Edwin W.Y.; Miura, Akito; Wright, Mathew D.; He, Qi; Walsby, Charles J.; Shimizu, Soji; Kobayashi, Nagao; Leznoff, Daniel B.

In: Chemistry - A European Journal, Vol. 18, No. 39, 24.09.2012, p. 12404-12410.

Research output: Contribution to journalArticle

Wong, Edwin W.Y. ; Miura, Akito ; Wright, Mathew D. ; He, Qi ; Walsby, Charles J. ; Shimizu, Soji ; Kobayashi, Nagao ; Leznoff, Daniel B. / Gold(II) phthalocyanine revisited : Synthesis and spectroscopic properties of gold(III) phthalocyanine and an unprecedented ring-contracted phthalocyanine analogue. In: Chemistry - A European Journal. 2012 ; Vol. 18, No. 39. pp. 12404-12410.
@article{49b592bb1c7044fe8e2dc10ae67ea136,
title = "Gold(II) phthalocyanine revisited: Synthesis and spectroscopic properties of gold(III) phthalocyanine and an unprecedented ring-contracted phthalocyanine analogue",
abstract = "In 1965, gold(II) phthalocyanine (AuPc, 1) was described to be synthesized from unsubstituted 1,3-diiminoisoindoline and gold powder or AuBr. Compound 1 has been regarded as a rare example of a paramagnetic gold(II) complex. However, its chemistry, especially the oxidation state of the central gold ion, has not been previously explored due to the inherent insolubility of 1 caused by its unsubstituted structure. In our attempt to synthesize soluble AuPcs by using 5,6-di-substituted 1,3-diiminoisoindolines, gold(III) phthalocyanine chloride (3) and a gold(III) complex of an unprecedented ring-contracted phthalocyanine analogue ([18]tribenzo-pentaaza-triphyrin(4,1,1), 4) were isolated. With this discrepant result from the original literature in hand, a reinvestigation of the original AuPc synthesis by using unsubstituted 1,3-diiminoisoindoline and various gold salts (including gold powder and AuBr) was performed, finding that only unsubstituted analogues of 3 and 4 or free-base phthalocyanine were obtained.",
author = "Wong, {Edwin W.Y.} and Akito Miura and Wright, {Mathew D.} and Qi He and Walsby, {Charles J.} and Soji Shimizu and Nagao Kobayashi and Leznoff, {Daniel B.}",
year = "2012",
month = "9",
day = "24",
doi = "10.1002/chem.201201701",
language = "English",
volume = "18",
pages = "12404--12410",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "39",

}

TY - JOUR

T1 - Gold(II) phthalocyanine revisited

T2 - Synthesis and spectroscopic properties of gold(III) phthalocyanine and an unprecedented ring-contracted phthalocyanine analogue

AU - Wong, Edwin W.Y.

AU - Miura, Akito

AU - Wright, Mathew D.

AU - He, Qi

AU - Walsby, Charles J.

AU - Shimizu, Soji

AU - Kobayashi, Nagao

AU - Leznoff, Daniel B.

PY - 2012/9/24

Y1 - 2012/9/24

N2 - In 1965, gold(II) phthalocyanine (AuPc, 1) was described to be synthesized from unsubstituted 1,3-diiminoisoindoline and gold powder or AuBr. Compound 1 has been regarded as a rare example of a paramagnetic gold(II) complex. However, its chemistry, especially the oxidation state of the central gold ion, has not been previously explored due to the inherent insolubility of 1 caused by its unsubstituted structure. In our attempt to synthesize soluble AuPcs by using 5,6-di-substituted 1,3-diiminoisoindolines, gold(III) phthalocyanine chloride (3) and a gold(III) complex of an unprecedented ring-contracted phthalocyanine analogue ([18]tribenzo-pentaaza-triphyrin(4,1,1), 4) were isolated. With this discrepant result from the original literature in hand, a reinvestigation of the original AuPc synthesis by using unsubstituted 1,3-diiminoisoindoline and various gold salts (including gold powder and AuBr) was performed, finding that only unsubstituted analogues of 3 and 4 or free-base phthalocyanine were obtained.

AB - In 1965, gold(II) phthalocyanine (AuPc, 1) was described to be synthesized from unsubstituted 1,3-diiminoisoindoline and gold powder or AuBr. Compound 1 has been regarded as a rare example of a paramagnetic gold(II) complex. However, its chemistry, especially the oxidation state of the central gold ion, has not been previously explored due to the inherent insolubility of 1 caused by its unsubstituted structure. In our attempt to synthesize soluble AuPcs by using 5,6-di-substituted 1,3-diiminoisoindolines, gold(III) phthalocyanine chloride (3) and a gold(III) complex of an unprecedented ring-contracted phthalocyanine analogue ([18]tribenzo-pentaaza-triphyrin(4,1,1), 4) were isolated. With this discrepant result from the original literature in hand, a reinvestigation of the original AuPc synthesis by using unsubstituted 1,3-diiminoisoindoline and various gold salts (including gold powder and AuBr) was performed, finding that only unsubstituted analogues of 3 and 4 or free-base phthalocyanine were obtained.

UR - http://www.scopus.com/inward/record.url?scp=84866357393&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84866357393&partnerID=8YFLogxK

U2 - 10.1002/chem.201201701

DO - 10.1002/chem.201201701

M3 - Article

C2 - 22933175

AN - SCOPUS:84866357393

VL - 18

SP - 12404

EP - 12410

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 39

ER -