Synthesis, characterization, photophysics, and photochemistry of peripherally substituted tetrakis(quinolinylethylenephenoxy)-substituted zinc() phthalocyanines

In this work, 2-chloro-6-methoxyquinoline-3-carbaldehyde was reacted with [4-(3,4-dicyanophenoxy)phenyl]acetic acid to obtain 2-(3,4-dicyanophenoxy)phenyl-4-(2-chloro-6-methoxyquinolin-3-yl)-3-butenoic acid as a phthalocyanine precursor. This compound was heated in 2-dimethylaminoethanol in the pres...

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Bibliographic Details
Published in:New journal of chemistry 2021-06, Vol.45 (22), p.9912-9921
Main Authors: Özdemir, Mücahit, Artuç, Gamze Özgül, Akkurt, Barbaros, Yalç n, Bahattin, Salan, Ümit, Durmu, Mahmut, Bulut, Mustafa
Format: Article
Language:English
Subjects:
Acetic acid
Acids
Fluorescence
Photochemistry
Photodynamic therapy
Quinoline
Singlet oxygen
Substitution reactions
Thiols
Zinc acetate
Zinc compounds
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Summary:In this work, 2-chloro-6-methoxyquinoline-3-carbaldehyde was reacted with [4-(3,4-dicyanophenoxy)phenyl]acetic acid to obtain 2-(3,4-dicyanophenoxy)phenyl-4-(2-chloro-6-methoxyquinolin-3-yl)-3-butenoic acid as a phthalocyanine precursor. This compound was heated in 2-dimethylaminoethanol in the presence of zinc acetate to yield 2,9(10),16(17),23(24)-tetrakis[2-phenoxy-4-(2-chloro-6-methoxyquinolin-3-yl)-3-butenoic acid] substituted zinc( ii ) phthalocyanine. Some thiols, namely n -butanethiol (R 1 ), n -hexanethiol (R 2 ), 3-sulfanylpropionic acid (R 3 ), and 7-sulfanyl-2 H -1-benzopyran-2-one (R 4 ), were reacted with this zinc( ii ) phthalocyanine compound. Nucleophilic aromatic substitution reaction occurred at the chloro substituent of the respective quinoline on the phthalocyanine framework. The fluorescence behavior, singlet oxygen generation, and photostability properties of these novel phthalocyanines were investigated. These compounds may be potential photosensitizers for photodynamic therapy and deserve further study. Quinoline substituted zinc phthalocyanine derivatives were synthesized and characterized, and their photophysical and photochemical properties were investigated.
ISSN:1144-0546
1369-9261
DOI:10.1039/d1nj00854d