Synthesis and spectroscopic investigation of boronic esters of metal-free fluorinated and non-fluorinated phthalocyanines

İbrahim Özçeşmeci; Mukaddes Özçeşmeci; Ahmet Gül; Esin Hamuryudan

doi:10.1016/j.synthmet.2016.11.022

Synthesis and spectroscopic investigation of boronic esters of metal-free fluorinated and non-fluorinated phthalocyanines

İbrahim Özçeşmeci, Mukaddes Özçeşmeci^*, Ahmet Gül, Esin Hamuryudan

^*Corresponding author for this work

Department of Chemistry

Istanbul Technical University

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

19 Citations (Scopus)

Abstract

Phthalonitriles and metal-free phthalocyanines substituted with 2,3-dihydroxypropoxy and [2,3,5,6-tetrafluoro-4-(2,3-dihydroxypropoxy)]benzyloxy groups were synthesized. Their complexes with phenylboronic acid were prepared in THF at reflux in the presence of molecular sieves. The new compounds were characterized by using elemental analyses, FT-IR, UV–vis, ¹H NMR, ¹⁹F NMR, ¹¹B NMR, and MALDI-TOF MS spectral data. Aggregation tendency of phthalocyanine complexes in relation to their concentrations were investigated by changes in their absorption spectra. Furthermore, photophysical and photochemical properties of metal-free phthalocyanines were investigated in ethanol and dichloromethane. The fluorescence quenching properties of synthesized phthalocyanines were investigated using 1,4-benzoquinone in dichloromethane.

Original language	English
Pages (from-to)	344-350
Number of pages	7
Journal	Synthetic Metals
Volume	222
DOIs	https://doi.org/10.1016/j.synthmet.2016.11.022
Publication status	Published - 1 Dec 2016

Bibliographical note

Publisher Copyright:
© 2016 Elsevier B.V.

Funding

This work was supported by the Research Fund of the Istanbul Technical University . AG thanks Turkish Academy of Sciences (TUBA) for partial support.

Funders	Funder number
Istanbul Teknik Üniversitesi

Keywords

Aggregation
Boronic ester
Fluorescence
Fluorine
Phthalocyanines
Synthesis

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10.1016/j.synthmet.2016.11.022

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title = "Synthesis and spectroscopic investigation of boronic esters of metal-free fluorinated and non-fluorinated phthalocyanines",

abstract = "Phthalonitriles and metal-free phthalocyanines substituted with 2,3-dihydroxypropoxy and [2,3,5,6-tetrafluoro-4-(2,3-dihydroxypropoxy)]benzyloxy groups were synthesized. Their complexes with phenylboronic acid were prepared in THF at reflux in the presence of molecular sieves. The new compounds were characterized by using elemental analyses, FT-IR, UV–vis, 1H NMR, 19F NMR, 11B NMR, and MALDI-TOF MS spectral data. Aggregation tendency of phthalocyanine complexes in relation to their concentrations were investigated by changes in their absorption spectra. Furthermore, photophysical and photochemical properties of metal-free phthalocyanines were investigated in ethanol and dichloromethane. The fluorescence quenching properties of synthesized phthalocyanines were investigated using 1,4-benzoquinone in dichloromethane.",

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T1 - Synthesis and spectroscopic investigation of boronic esters of metal-free fluorinated and non-fluorinated phthalocyanines

AU - Özçeşmeci, İbrahim

AU - Özçeşmeci, Mukaddes

AU - Gül, Ahmet

AU - Hamuryudan, Esin

PY - 2016/12/1

Y1 - 2016/12/1

N2 - Phthalonitriles and metal-free phthalocyanines substituted with 2,3-dihydroxypropoxy and [2,3,5,6-tetrafluoro-4-(2,3-dihydroxypropoxy)]benzyloxy groups were synthesized. Their complexes with phenylboronic acid were prepared in THF at reflux in the presence of molecular sieves. The new compounds were characterized by using elemental analyses, FT-IR, UV–vis, 1H NMR, 19F NMR, 11B NMR, and MALDI-TOF MS spectral data. Aggregation tendency of phthalocyanine complexes in relation to their concentrations were investigated by changes in their absorption spectra. Furthermore, photophysical and photochemical properties of metal-free phthalocyanines were investigated in ethanol and dichloromethane. The fluorescence quenching properties of synthesized phthalocyanines were investigated using 1,4-benzoquinone in dichloromethane.

AB - Phthalonitriles and metal-free phthalocyanines substituted with 2,3-dihydroxypropoxy and [2,3,5,6-tetrafluoro-4-(2,3-dihydroxypropoxy)]benzyloxy groups were synthesized. Their complexes with phenylboronic acid were prepared in THF at reflux in the presence of molecular sieves. The new compounds were characterized by using elemental analyses, FT-IR, UV–vis, 1H NMR, 19F NMR, 11B NMR, and MALDI-TOF MS spectral data. Aggregation tendency of phthalocyanine complexes in relation to their concentrations were investigated by changes in their absorption spectra. Furthermore, photophysical and photochemical properties of metal-free phthalocyanines were investigated in ethanol and dichloromethane. The fluorescence quenching properties of synthesized phthalocyanines were investigated using 1,4-benzoquinone in dichloromethane.

KW - Aggregation

KW - Boronic ester

KW - Fluorescence

KW - Fluorine

KW - Phthalocyanines

KW - Synthesis

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DO - 10.1016/j.synthmet.2016.11.022

M3 - Article

AN - SCOPUS:85002293032

SN - 0379-6779

VL - 222

SP - 344

EP - 350

JO - Synthetic Metals

JF - Synthetic Metals

ER -

Synthesis and spectroscopic investigation of boronic esters of metal-free fluorinated and non-fluorinated phthalocyanines

Abstract

Bibliographical note

Funding

Keywords

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