Tetra- and octa-[4-(2-hydroxyethyl)phenoxy bearing novel metal-free and zinc(II) phthalocyanines: Synthesis, characterization and investigation of photophysicochemical properties

被引:18
作者
Koksoy, Baybars [1 ]
Durmus, Mahmut [2 ]
Bulut, Mustafa [1 ]
机构
[1] Marmara Univ, Dept Chem, TR-34722 Istanbul, Turkey
[2] Gebze Tech Univ, Dept Chem, TR-41400 Gebze, Kocaeli, Turkey
关键词
Phthalocyanine; Zinc(II); Metal-free; Photochemical; Photophysical; Singlet oxygen; PHOTOCHEMICAL PROPERTIES; PHOTOSENSITIZERS; SUBSTITUENTS; AGGREGATION; WATER;
D O I
10.1016/j.jlumin.2014.12.044
中图分类号
O43 [光学];
学科分类号
070207 ; 0803 ;
摘要
In this study, four novel phthalonitriles (1-4) and their corresponding metal-free (5-8) and zinc(II) phthalocyanine derivatives (9-12) bearing 4-(hydroxyethyl)phenoxy groups were synthesized. These novel compounds were characterized by IR, elemental analyses, H-1-NMR, UV-vis, and MALDI-TOF spectral data. Furthermore, photophysical (fluorescence quantum yields and lifetimes) and photochemical properties (singlet oxygen generation and photodegradation quantum yields) of these phthalocyanines were investigated in dimethylsulfoxide. The studied zinc(II) phthalocyanines generated highly singlet oxygen which is very important for the photodynamic therapy (PDT) of cancer. The fluorescence quenching behaviour of the newly synthesized phthalocyanine compounds were also investigated using 1,4-benzoquinone. (C) 2014 Elsevier B.V. All rights reserved.
引用
收藏
页码:95 / 102
页数:8
相关论文
共 50 条
[31]   Preparation, characterization, electrochemistry and in situ spectroelectrochemistry of novel α-tetra[7-oxo-3-(2-chloro-4-fluorophenyl)coumarin]-substituted metal-free, cobalt and zinc phthalocyanines [J].
Alemdar, Aydin ;
Ozkaya, Ali Riza ;
Bulut, Mustafa .
SYNTHETIC METALS, 2010, 160 (13-14) :1556-1565
[32]   Novel peripherally tetra substituted metal-free, cobalt(II), copper(II) and manganese(III) phthalocyanines bearing polyethoxy chain attached by 2,6-diphenylphenol groups: synthesis, characterization and their electrochemical studies [J].
Ayşe Aktaş Kamiloğlu ;
İrfan Acar ;
Zekeriya Biyiklioglu .
Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2017, 88 :219-228
[33]   Novel peripherally tetra substituted metal-free, cobalt(II), copper(II) and manganese(III) phthalocyanines bearing polyethoxy chain attached by 2,6-diphenylphenol groups: synthesis, characterization and their electrochemical studies [J].
Kamiloglu, Ayse Aktas ;
Acar, Irfan ;
Biyiklioglu, Zekeriya .
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2017, 88 (3-4) :219-228
[34]   Synthesis, characterization and aggregation and fluorescence properties of novel highly soluble zinc phthalocyanines bearing tetrakis-4-(3-(piperidin-1-yl)phenoxy) with tetra and dodecachloro substituents [J].
Palanisamy Muthukumar ;
Hak-Soo Kim ;
Kyo-Sun Ku ;
Jong Ho Park ;
Young-A. Son .
Fibers and Polymers, 2016, 17 :553-559
[35]   1,2,3-Triazole incorporated coumarin carrying metal-free, Zn(II), Mg(II) phthalocyanines: Synthesis, characterization, theoretical studies, photophysical and photochemical properties [J].
Ozdemir, Mucahit ;
Abliatipova, Aziza ;
Benian, Sueda ;
Yalcin, Bahattin ;
Salan, Umit ;
Durmus, Mahmut ;
Bulut, Mustafa .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2020, 403
[36]   Synthesis, characterization and electrical properties of novel metal-free, Co(II), Cu(II), Fe(II), Mn(II), Sn(II) phthalocyanines peripherally tetra-substituted with 2,3-dihydro-1H-inden-5-yloxy moiety [J].
Odabas, Zafer ;
Altindal, Ahmet ;
Bulut, Mustafa .
SYNTHETIC METALS, 2011, 161 (15-16) :1742-1752
[37]   Synthesis, characterization, photophysical and photochemical properties of peripherally tetra-1,2,4-triazol-3-ylthio substituted metal-free phthalocyanine and its zinc(II) and lead(II) derivatives [J].
Demirbas, Umit ;
Yanik, Hulya ;
Akcay, Hakki Turker ;
Durmus, Mahmut ;
Bekircan, Olcay ;
Kantekin, Halit .
JOURNAL OF COORDINATION CHEMISTRY, 2022, 75 (3-4) :448-456
[38]   Microwave assisted synthesis of novel zinc(II) phthalocyanines bearing 1,3-diazido-2-propanoxy functional groups and investigation of their photochemical properties [J].
Sari, Sait ;
Durmus, Mahmut ;
Bulut, Mustafa .
TETRAHEDRON LETTERS, 2016, 57 (10) :1124-1128
[39]   Synthesis, spectroscopic, electrochemical and spectroelectrochemical properties of metal free, manganese, and cobalt phthalocyanines bearing peripherally octakis-[4-(thiophen-3-yl)-phenoxy] substituents [J].
Ugur, Ahmet Lutfi ;
Erdogmus, Ali ;
Koca, Atif ;
Avciata, Ulvi .
POLYHEDRON, 2010, 29 (18) :3310-3317
[40]   SYNTHESIS, CHARACTERIZATION, ELECTROCHEMICAL PROPERTIES OF METAL-FREE AND METALLOPHTHALOCYANINES BEARING 2-BENZYLPHENOXY SUBSTITUENTS AND INVESTIGATION OF THEIR BIOLOGICAL ACTIVITIES [J].
Saglam, Meltem Betul ;
Inan Bektas, Kadriye ;
Uysal, Ahmet ;
Guler, Halil Ibrahim ;
Saglam, Aykut ;
Biyiklioglu, Zekeriya .
REVUE ROUMAINE DE CHIMIE, 2018, 63 (10) :881-895