α- and β-Substituted Metal-Free Phthalocyanines: Synthesis, Photophysical and Electrochemical Properties

Two novel phthalonitrile derivatives, bearing two hexyloxy groups and a benzodioxin (or a naphthodioxin) annulated ring, along with their corresponding metal-free phthalocyanines (H<sub>2</sub>Pc) were prepared. FT-IR, mass, electronic absorption, <sup>1</sup>H NMR, and <s...

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Main Authors:	Hande Pekbelgin Karaoğlu, Ayfer Kalkan Burat
Format:	Article
Language:	English
Published:	MDPI AG 2020-01-01
Series:	Molecules
Subjects:	fluorescence hexadeca substitution phthalocyanine photophysics synthesis electrochemistry
Online Access:	https://www.mdpi.com/1420-3049/25/2/363

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record_format	Article
spelling	doaj-09cf4950e84d4ddfa7c5270769002c682020-11-25T01:42:38ZengMDPI AGMolecules1420-30492020-01-0125236310.3390/molecules25020363molecules25020363α- and β-Substituted Metal-Free Phthalocyanines: Synthesis, Photophysical and Electrochemical PropertiesHande Pekbelgin Karaoğlu0Ayfer Kalkan Burat1Chemistry Department, Technical University of Istanbul, İstanbul TR34469, TurkeyChemistry Department, Technical University of Istanbul, İstanbul TR34469, TurkeyTwo novel phthalonitrile derivatives, bearing two hexyloxy groups and a benzodioxin (or a naphthodioxin) annulated ring, along with their corresponding metal-free phthalocyanines (H<sub>2</sub>Pc) were prepared. FT-IR, mass, electronic absorption, <sup>1</sup>H NMR, and <sup>13</sup>C 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 H<sub>2</sub>Pc 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.https://www.mdpi.com/1420-3049/25/2/363fluorescencehexadeca substitutionphthalocyaninephotophysicssynthesiselectrochemistry
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Hande Pekbelgin Karaoğlu Ayfer Kalkan Burat
spellingShingle	Hande Pekbelgin Karaoğlu Ayfer Kalkan Burat α- and β-Substituted Metal-Free Phthalocyanines: Synthesis, Photophysical and Electrochemical Properties Molecules fluorescence hexadeca substitution phthalocyanine photophysics synthesis electrochemistry
author_facet	Hande Pekbelgin Karaoğlu Ayfer Kalkan Burat
author_sort	Hande Pekbelgin Karaoğlu
title	α- and β-Substituted Metal-Free Phthalocyanines: Synthesis, Photophysical and Electrochemical Properties
title_short	α- and β-Substituted Metal-Free Phthalocyanines: Synthesis, Photophysical and Electrochemical Properties
title_full	α- and β-Substituted Metal-Free Phthalocyanines: Synthesis, Photophysical and Electrochemical Properties
title_fullStr	α- and β-Substituted Metal-Free Phthalocyanines: Synthesis, Photophysical and Electrochemical Properties
title_full_unstemmed	α- and β-Substituted Metal-Free Phthalocyanines: Synthesis, Photophysical and Electrochemical Properties
title_sort	α- and β-substituted metal-free phthalocyanines: synthesis, photophysical and electrochemical properties
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2020-01-01
description	Two novel phthalonitrile derivatives, bearing two hexyloxy groups and a benzodioxin (or a naphthodioxin) annulated ring, along with their corresponding metal-free phthalocyanines (H<sub>2</sub>Pc) were prepared. FT-IR, mass, electronic absorption, <sup>1</sup>H NMR, and <sup>13</sup>C 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 H<sub>2</sub>Pc 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.
topic	fluorescence hexadeca substitution phthalocyanine photophysics synthesis electrochemistry
url	https://www.mdpi.com/1420-3049/25/2/363
work_keys_str_mv	AT handepekbelginkaraoglu aandbsubstitutedmetalfreephthalocyaninessynthesisphotophysicalandelectrochemicalproperties AT ayferkalkanburat aandbsubstitutedmetalfreephthalocyaninessynthesisphotophysicalandelectrochemicalproperties
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α- and β-Substituted Metal-Free Phthalocyanines: Synthesis, Photophysical and Electrochemical Properties

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