Novel metallophthalocyanines with bulky 4-[3,4-bis(benzyloxy)benzylidene]aminophenoxy substituents

Altuğ Mert Sevim; Murat Yüzeroğlu; Ahmet Gül

doi:10.1007/s00706-020-02639-w

Novel metallophthalocyanines with bulky 4-[3,4-bis(benzyloxy)benzylidene]aminophenoxy substituents

Altuğ Mert Sevim, Murat Yüzeroğlu, Ahmet Gül^*

^*Corresponding author for this work

Department of Chemistry

Istanbul Technical University

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

7 Citations (Scopus)

Abstract

Abstract: Novel metallophthalocyanines substituted with four peripheral 4-[3,4-bis(benzyloxy)benzylidene]aminophenoxy groups were prepared by Schiff base condensation of 4-aminophenoxy-substituted phthalocyanines with 3,4-bis(benzyloxy)benzaldehyde. The structures were elucidated with elemental analysis, Fourier transform infrared spectroscopy, proton nuclear magnetic resonance spectrometry, and matrix assisted laser desorption ionization-time of flight spectrometry along with Ultraviolet–Visible spectrophotometry. In the studied concentration range of 1–10 × 10⁻⁶ M, no appreciable aggregation of the new species was detected. In tetrahydrofuran, the fluorescent quantum yield Φ_F value of the zinc phthalocyanine was lower than the unsubstituted ZnPc (Φ_F = 0.25) due to the peripheral [3,4-bis(benzyloxy)benzylidene]aminophenoxy substituents which surely caused fluorescence quenching. The zinc phthalocyanine showed fluorescent quenching by the addition of 1,4-benzoquinone in tetrahydrofuran with obedience to Stern–Volmer kinetics. Graphic abstract: [Figure not available: see fulltext.]

Original language	English
Pages (from-to)	1059-1068
Number of pages	10
Journal	Monatshefte fur Chemie
Volume	151
Issue number	7
DOIs	https://doi.org/10.1007/s00706-020-02639-w
Publication status	Published - 1 Jul 2020

Bibliographical note

Publisher Copyright:
© 2020, Springer-Verlag GmbH Austria, part of Springer Nature.

Funding

Istanbul Technical University Research Fund kindly supported this work. TUBA (Turkish Academy of Sciences) provided partial support to AG. Istanbul Technical University Research Fund kindly supported this work. TUBA (Turkish Academy of Sciences) provided partial support to AG.

Funders	Funder number
TUBA
Türkiye Bilimler Akademisi
Istanbul Teknik Üniversitesi

Keywords

Aggregation
Fluorescence spectroscopy
Phthalocyanines
Quenching
Schiff bases

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title = "Novel metallophthalocyanines with bulky 4-[3,4-bis(benzyloxy)benzylidene]aminophenoxy substituents",

abstract = "Abstract: Novel metallophthalocyanines substituted with four peripheral 4-[3,4-bis(benzyloxy)benzylidene]aminophenoxy groups were prepared by Schiff base condensation of 4-aminophenoxy-substituted phthalocyanines with 3,4-bis(benzyloxy)benzaldehyde. The structures were elucidated with elemental analysis, Fourier transform infrared spectroscopy, proton nuclear magnetic resonance spectrometry, and matrix assisted laser desorption ionization-time of flight spectrometry along with Ultraviolet–Visible spectrophotometry. In the studied concentration range of 1–10 × 10−6 M, no appreciable aggregation of the new species was detected. In tetrahydrofuran, the fluorescent quantum yield ΦF value of the zinc phthalocyanine was lower than the unsubstituted ZnPc (ΦF = 0.25) due to the peripheral [3,4-bis(benzyloxy)benzylidene]aminophenoxy substituents which surely caused fluorescence quenching. The zinc phthalocyanine showed fluorescent quenching by the addition of 1,4-benzoquinone in tetrahydrofuran with obedience to Stern–Volmer kinetics. Graphic abstract: [Figure not available: see fulltext.]",

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note = "Publisher Copyright: {\textcopyright} 2020, Springer-Verlag GmbH Austria, part of Springer Nature.",

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doi = "10.1007/s00706-020-02639-w",

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T1 - Novel metallophthalocyanines with bulky 4-[3,4-bis(benzyloxy)benzylidene]aminophenoxy substituents

AU - Sevim, Altuğ Mert

AU - Yüzeroğlu, Murat

AU - Gül, Ahmet

PY - 2020/7/1

Y1 - 2020/7/1

N2 - Abstract: Novel metallophthalocyanines substituted with four peripheral 4-[3,4-bis(benzyloxy)benzylidene]aminophenoxy groups were prepared by Schiff base condensation of 4-aminophenoxy-substituted phthalocyanines with 3,4-bis(benzyloxy)benzaldehyde. The structures were elucidated with elemental analysis, Fourier transform infrared spectroscopy, proton nuclear magnetic resonance spectrometry, and matrix assisted laser desorption ionization-time of flight spectrometry along with Ultraviolet–Visible spectrophotometry. In the studied concentration range of 1–10 × 10−6 M, no appreciable aggregation of the new species was detected. In tetrahydrofuran, the fluorescent quantum yield ΦF value of the zinc phthalocyanine was lower than the unsubstituted ZnPc (ΦF = 0.25) due to the peripheral [3,4-bis(benzyloxy)benzylidene]aminophenoxy substituents which surely caused fluorescence quenching. The zinc phthalocyanine showed fluorescent quenching by the addition of 1,4-benzoquinone in tetrahydrofuran with obedience to Stern–Volmer kinetics. Graphic abstract: [Figure not available: see fulltext.]

AB - Abstract: Novel metallophthalocyanines substituted with four peripheral 4-[3,4-bis(benzyloxy)benzylidene]aminophenoxy groups were prepared by Schiff base condensation of 4-aminophenoxy-substituted phthalocyanines with 3,4-bis(benzyloxy)benzaldehyde. The structures were elucidated with elemental analysis, Fourier transform infrared spectroscopy, proton nuclear magnetic resonance spectrometry, and matrix assisted laser desorption ionization-time of flight spectrometry along with Ultraviolet–Visible spectrophotometry. In the studied concentration range of 1–10 × 10−6 M, no appreciable aggregation of the new species was detected. In tetrahydrofuran, the fluorescent quantum yield ΦF value of the zinc phthalocyanine was lower than the unsubstituted ZnPc (ΦF = 0.25) due to the peripheral [3,4-bis(benzyloxy)benzylidene]aminophenoxy substituents which surely caused fluorescence quenching. The zinc phthalocyanine showed fluorescent quenching by the addition of 1,4-benzoquinone in tetrahydrofuran with obedience to Stern–Volmer kinetics. Graphic abstract: [Figure not available: see fulltext.]

KW - Aggregation

KW - Fluorescence spectroscopy

KW - Phthalocyanines

KW - Quenching

KW - Schiff bases

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Novel metallophthalocyanines with bulky 4-[3,4-bis(benzyloxy)benzylidene]aminophenoxy substituents

Abstract

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Keywords

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