Synthesis and photophysical properties of metallophthalocyanines substituted with a benzofuran based fluoroprobe

Meryem N. Yarasir; Mehmet Kandaz; Orhan Güney; Bekir Salih

doi:10.1016/j.saa.2012.02.111

Synthesis and photophysical properties of metallophthalocyanines substituted with a benzofuran based fluoroprobe

Meryem N. Yarasir, Mehmet Kandaz^*, Orhan Güney, Bekir Salih

^*Corresponding author for this work

Department of Chemistry

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

12 Citations (Scopus)

Abstract

The synthesis, characterization and photophysical properties of the tetra- {6-(-benzofuran-2-carboxylate)-hexylthio} substituted copper(II), cobalt(II), manganese(III) and zinc (II) phthalocyanines, {M[Pc(β-S(CH ₂) ₆OCOBz-Furan) ₄], which were derived from 6-(3,4-dicyanophenylthio)-hexyl-2-benzofuranate (BzF) (1-4) are reported for the first time. The new compounds have been synthesized and fully characterized by elemental analysis, FTIR, UV-vis, ¹H- and ¹³C NMR, MS (Maldi-TOF). In this work, we also report the effects of peripherally bound BzF substituent on the photophysical properties of metallo phthalocyanine derivatives. The effects of changing the central metal ions on quantum yield are discussed. It was found that the substitution of BzF groups on the framework of phthalocyanines diminished the fluorescence quantum yield of these complexes depending on paramagnetic behavior of central metal atoms. In addition, central metal atoms like Co and Cu also caused to decrease in quantum yield of phthalocyanine backbone.

Original language	English
Pages (from-to)	379-383
Number of pages	5
Journal	Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Volume	93
DOIs	https://doi.org/10.1016/j.saa.2012.02.111
Publication status	Published - Jul 2012

Funding

We thank the Research Funds of TUBİTAK (TBAG: Project no: 108T094) and ITU (BAP, Project No: 90204) for financial support.

Funders	Funder number
TUBİTAK	108T094
International Technological University	90204

Keywords

Aggregation
Cobalt
Copper
Fluorescence quantum yield
Manganese and Zinc
Phthalocyanine

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abstract = "The synthesis, characterization and photophysical properties of the tetra- {6-(-benzofuran-2-carboxylate)-hexylthio} substituted copper(II), cobalt(II), manganese(III) and zinc (II) phthalocyanines, {M[Pc(β-S(CH 2) 6OCOBz-Furan) 4], which were derived from 6-(3,4-dicyanophenylthio)-hexyl-2-benzofuranate (BzF) (1-4) are reported for the first time. The new compounds have been synthesized and fully characterized by elemental analysis, FTIR, UV-vis, 1H- and 13C NMR, MS (Maldi-TOF). In this work, we also report the effects of peripherally bound BzF substituent on the photophysical properties of metallo phthalocyanine derivatives. The effects of changing the central metal ions on quantum yield are discussed. It was found that the substitution of BzF groups on the framework of phthalocyanines diminished the fluorescence quantum yield of these complexes depending on paramagnetic behavior of central metal atoms. In addition, central metal atoms like Co and Cu also caused to decrease in quantum yield of phthalocyanine backbone.",

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author = "Yarasir, {Meryem N.} and Mehmet Kandaz and Orhan G{\"u}ney and Bekir Salih",

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AU - Yarasir, Meryem N.

AU - Kandaz, Mehmet

AU - Güney, Orhan

AU - Salih, Bekir

PY - 2012/7

Y1 - 2012/7

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AB - The synthesis, characterization and photophysical properties of the tetra- {6-(-benzofuran-2-carboxylate)-hexylthio} substituted copper(II), cobalt(II), manganese(III) and zinc (II) phthalocyanines, {M[Pc(β-S(CH 2) 6OCOBz-Furan) 4], which were derived from 6-(3,4-dicyanophenylthio)-hexyl-2-benzofuranate (BzF) (1-4) are reported for the first time. The new compounds have been synthesized and fully characterized by elemental analysis, FTIR, UV-vis, 1H- and 13C NMR, MS (Maldi-TOF). In this work, we also report the effects of peripherally bound BzF substituent on the photophysical properties of metallo phthalocyanine derivatives. The effects of changing the central metal ions on quantum yield are discussed. It was found that the substitution of BzF groups on the framework of phthalocyanines diminished the fluorescence quantum yield of these complexes depending on paramagnetic behavior of central metal atoms. In addition, central metal atoms like Co and Cu also caused to decrease in quantum yield of phthalocyanine backbone.

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KW - Copper

KW - Fluorescence quantum yield

KW - Manganese and Zinc

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JF - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

ER -

Synthesis and photophysical properties of metallophthalocyanines substituted with a benzofuran based fluoroprobe

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Keywords

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