Α- And β-substituted metal-free phthalocyanines: Synthesis, photophysical and electrochemical properties

Hande Pekbelgin Karaoglu; Ayfer Kalkan Burat

doi:10.3390/molecules25020363

Α- And β-substituted metal-free phthalocyanines: Synthesis, photophysical and electrochemical properties

Hande Pekbelgin Karaoglu^*, Ayfer Kalkan Burat

^*Corresponding author for this work

Department of Chemistry

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

11 Citations (Scopus)

Abstract

Two novel phthalonitrile derivatives, bearing two hexyloxy groups and a benzodioxin (or a naphthodioxin) annulated ring, along with their corresponding metal-free phthalocyanines (H₂Pc) were prepared. FT-IR, mass, electronic absorption, ¹H NMR, and ¹³C NMR spectroscopy were employed for the characterization of all compounds. The effect of hexadeca substituents on the photophysical properties of metal-free Pcs was investigated. Photophysical properties of H₂Pc were studied in tetrahydrofuran (THF). Fluorescent quantum yields of phthalocyanines (Pcs) were calculated and compared with the unsubstituted phthalocyanine. 1,4-Benzoquinone effectively quenched the fluorescence of these compounds in THF. Cyclic and square wave voltammetry methods were applied to metal-free phthalocyanines and Pc-centered oxidation and reduction processes were obtained.

Original language	English
Article number	363
Journal	Molecules
Volume	25
Issue number	2
DOIs	https://doi.org/10.3390/molecules25020363
Publication status	Published - 16 Jan 2020

Bibliographical note

Publisher Copyright:
© 2020 by the authors.

Funding

Funding: This work was supported by the Research Fund of the Istanbul Technical University.

Funders	Funder number
Istanbul Teknik Üniversitesi

Keywords

Electrochemistry
Fluorescence
Hexadeca substitution
Photophysics
Phthalocyanine
Synthesis

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10.3390/molecules25020363

Cite this

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title = "Α- And β-substituted metal-free phthalocyanines: Synthesis, photophysical and electrochemical properties",

abstract = "Two novel phthalonitrile derivatives, bearing two hexyloxy groups and a benzodioxin (or a naphthodioxin) annulated ring, along with their corresponding metal-free phthalocyanines (H2Pc) were prepared. FT-IR, mass, electronic absorption, 1H NMR, and 13C NMR spectroscopy were employed for the characterization of all compounds. The effect of hexadeca substituents on the photophysical properties of metal-free Pcs was investigated. Photophysical properties of H2Pc were studied in tetrahydrofuran (THF). Fluorescent quantum yields of phthalocyanines (Pcs) were calculated and compared with the unsubstituted phthalocyanine. 1,4-Benzoquinone effectively quenched the fluorescence of these compounds in THF. Cyclic and square wave voltammetry methods were applied to metal-free phthalocyanines and Pc-centered oxidation and reduction processes were obtained.",

keywords = "Electrochemistry, Fluorescence, Hexadeca substitution, Photophysics, Phthalocyanine, Synthesis",

author = "Karaoglu, \{Hande Pekbelgin\} and Burat, \{Ayfer Kalkan\}",

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doi = "10.3390/molecules25020363",

language = "English",

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TY - JOUR

T1 - Α- And β-substituted metal-free phthalocyanines

T2 - Synthesis, photophysical and electrochemical properties

AU - Karaoglu, Hande Pekbelgin

AU - Burat, Ayfer Kalkan

PY - 2020/1/16

Y1 - 2020/1/16

N2 - Two novel phthalonitrile derivatives, bearing two hexyloxy groups and a benzodioxin (or a naphthodioxin) annulated ring, along with their corresponding metal-free phthalocyanines (H2Pc) were prepared. FT-IR, mass, electronic absorption, 1H NMR, and 13C NMR spectroscopy were employed for the characterization of all compounds. The effect of hexadeca substituents on the photophysical properties of metal-free Pcs was investigated. Photophysical properties of H2Pc were studied in tetrahydrofuran (THF). Fluorescent quantum yields of phthalocyanines (Pcs) were calculated and compared with the unsubstituted phthalocyanine. 1,4-Benzoquinone effectively quenched the fluorescence of these compounds in THF. Cyclic and square wave voltammetry methods were applied to metal-free phthalocyanines and Pc-centered oxidation and reduction processes were obtained.

AB - Two novel phthalonitrile derivatives, bearing two hexyloxy groups and a benzodioxin (or a naphthodioxin) annulated ring, along with their corresponding metal-free phthalocyanines (H2Pc) were prepared. FT-IR, mass, electronic absorption, 1H NMR, and 13C NMR spectroscopy were employed for the characterization of all compounds. The effect of hexadeca substituents on the photophysical properties of metal-free Pcs was investigated. Photophysical properties of H2Pc were studied in tetrahydrofuran (THF). Fluorescent quantum yields of phthalocyanines (Pcs) were calculated and compared with the unsubstituted phthalocyanine. 1,4-Benzoquinone effectively quenched the fluorescence of these compounds in THF. Cyclic and square wave voltammetry methods were applied to metal-free phthalocyanines and Pc-centered oxidation and reduction processes were obtained.

KW - Electrochemistry

KW - Fluorescence

KW - Hexadeca substitution

KW - Photophysics

KW - Phthalocyanine

KW - Synthesis

UR - https://www.scopus.com/pages/publications/85078193004

U2 - 10.3390/molecules25020363

DO - 10.3390/molecules25020363

M3 - Article

AN - SCOPUS:85078193004

SN - 1420-3049

VL - 25

JO - Molecules

JF - Molecules

IS - 2

M1 - 363

ER -

Α- And β-substituted metal-free phthalocyanines: Synthesis, photophysical and electrochemical properties

Abstract

Bibliographical note

Funding

Keywords

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