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

被引:3
作者
Demirbas, Umit [1 ]
Yanik, Hulya [2 ]
Akcay, Hakki Turker [3 ]
Durmus, Mahmut [2 ]
Bekircan, Olcay [1 ]
Kantekin, Halit [1 ]
机构
[1] Karadeniz Tech Univ, Dept Chem, Trabzon, Turkey
[2] Gebze Tech Univ, Dept Chem, Kocaeli, Turkey
[3] Recep Tayyip Erdogan Univ, Fac Arts & Sci, Dept Chem, Rize, Turkey
关键词
Triazole; phthalocyanine; singlet oxygen; fluorescence quenching; photosensitizer; TRIAZOLES; DESIGN; NI(II); FILMS; ACID;
D O I
10.1080/00958972.2022.2053846
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Phthalonitrile (3) including 4-(4-fluorophenyl)-5-(4-methoxyphenyl)-4H-1,2,4-triazole-3-thio substituent and its peripherally tetra substituted metal-free (4), zinc(II) (5) and lead(II) (6) phthalocyanine derivatives were prepared and characterized by FTIR, mass, H-1-NMR and C-13-NMR spectroscopic data. All studied phthalocyanines had good solubility in common organic solvents and did not aggregate. The photophysical and photochemical behaviors of the phthalocyanine complexes (4-6) were examined in DMSO to determinate their PDT potential. Singlet oxygen, fluorescence and photodegradation quantum yields showed that zinc(II) phthalocyanine (5) has potential as Type II photosensitizer for PDT applications.
引用
收藏
页码:448 / 456
页数:9
相关论文
共 41 条
[1]   Design, synthesis and molecular modeling study of acylated 1,2,4-triazole-3-acetates with potential anti-inflammatory activity [J].
Abdel-Megeed, Ashraf M. ;
Abdel-Rahman, Hamdy A. ;
Alkaramany, Gamal-Eldien S. ;
El-Gendy, Mahmoud A. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (01) :117-123
[2]   Computational studies on the anastrozole and letrozole, effective chemotherapy drugs against breast cancer [J].
Akcay, Hakki Turker ;
Bayrak, Riza .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2014, 122 :142-152
[3]   Novel triazole bearing zinc(II) and magnesium(II) metallo-phthalocyanines: Synthesis, characterization, photophysical and photochemical properties [J].
Akcay, Hakki Turker ;
Piskin, Mehmet ;
Demirbas, Umit ;
Bayrak, Riza ;
Durmus, Mahmut ;
Mentese, Emre ;
Kantekin, Halit .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2013, 745 :379-386
[4]   Design, synthesis, biological evaluation and molecular docking studies of novel 1H-1,2,3-Triazole derivatives as potent inhibitors of carbonic anhydrase, acetylcholinesterase and aldose reductase [J].
Anil, Derya Aktas ;
Aydin, Busra Ozturk ;
Demir, Yeliz ;
Turkmenoglu, Burcin .
JOURNAL OF MOLECULAR STRUCTURE, 2022, 1257
[5]  
Atilla D, 2007, EUR J INORG CHEM, P3573
[6]   Discovery of novel hybrids of diaryl-1,2,4-triazoles and caffeic acid as dual inhibitors of cyclooxygenase-2 and 5-lipoxygenase for cancer therapy [J].
Cai, Hao ;
Huang, Xiaojing ;
Xu, Shengtao ;
Shen, Hao ;
Zhang, Pengfei ;
Huang, Yue ;
Jiang, Jieyun ;
Sun, Yijun ;
Jiang, Bo ;
Wu, Xiaoming ;
Yao, Hequan ;
Xu, Jingyi .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 108 :89-103
[7]   Synthesis, characterization and comparative studies on the photophysical and photochemical properties of metal-free and zinc(II) phthalocyanines with phenyloxyacetic acid functionalities [J].
Camur, Meryem ;
Durmus, Mahmut ;
Bulut, Mustafa .
POLYHEDRON, 2011, 30 (12) :1935-1944
[8]   Synthesis and insecticidal activity of 1,2,4-triazole derivatives [J].
Chai, B ;
Qian, XH ;
Cao, S ;
Liu, HD ;
Song, GH .
ARKIVOC, 2003, :141-145
[9]   Peripherally and non-peripherally tetra-benzothiazole substituted metal-free zinc (II) and lead (II) phthalocyanines: Synthesis, characterization, and investigation of photophysical and photochemical properties [J].
Demirbas, Umit ;
Gol, Cem ;
Barut, Burak ;
Bayrak, Riza ;
Durmus, Mahmut ;
Kantekin, Halit ;
Degirmencioglu, Ismail .
JOURNAL OF MOLECULAR STRUCTURE, 2017, 1130 :677-687
[10]   Synthesis and electrochemical characterization of tetra-(5-chloro-2-(2,4-dichlorophenoxy)phenol) substituted Ni(II), Fe(II) and Cu(II) metallophthalocyanines [J].
Demirbas, Umit ;
Kobak, Rabia Zeynep Uslu ;
Barut, Burak ;
Bayrak, Riza ;
Koca, Atif ;
Kantekin, Halit .
SYNTHETIC METALS, 2016, 215 :7-13