Novel phthalocyanines bearing 7-oxy-3-(3,5-difluorophenyl)coumarin moieties: Synthesis, characterization, photophysical and photochemical properties

被引：22
|
作者：
Erdogan, Tolga [1 ]
Bulut, Mustafa [1 ]
Camur, Meryem [2 ]
机构：
[1] Marmara Univ, Dept Chem, TR-34722 Istanbul, Turkey
[2] Kirklareli Univ, Dept Chem, TR-39100 Kirklareli, Turkey
来源：
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY | 2015年 / 300卷
关键词：
Phthalocyanine; Coumarin; Zinc; Indium; Photodegradation; Singlet oxygen; PHOTODYNAMIC THERAPY; ZINC(II) PHTHALOCYANINE; INDIUM PHTHALOCYANINES; SUBSTITUTED GALLIUM; OPTICAL-PROPERTIES; COUMARIN; PHOTOSENSITIZERS; DERIVATIVES;
D O I：
10.1016/j.jphotochem.2014.12.005
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Two novel phthalonitriles,7-(2,3-dicyanophenoxy)-3-(3,5-difluorophenyl) coumarin (2), 7-(3,4-dicyanophenoxy)-3-(3,5-difluorophenyl) coumarin (3), and corresponding zinc(II)-, indium(III) phthalocyanines were prepared. Additionally, photophysical (fluorescence quantum yields and lifetimes), photochemical (singlet oxygen generation and photodegradation under light irradiation) and spectral properties of the resulting peripherally/non-peripherally tetra 7-oxy-3-(3,5-difluorophenyl) coumarin substituted zinc (II) and indium (III) phthalocyanines (4-7) were investigated. All compounds (1-7) were characterized by elemental analysis, IR, H-1 NMR, mass and UV-vis spectral data. The obtained 7-oxy-3-(3,5-difluorophenyl) coumarin bearing pure zinc (II) and indium (III) phthalocyanine complexes were well soluble in organic solvents and displayed good singlet-oxygen generation and appropriate photodegradation. (C) 2014 Elsevier B.V. All rights reserved.
引用
收藏
页码：6 / 14
页数：9
相关论文
共 50 条
  • [41] Electrical and gas sensing properties of novel cobalt(II), copper(II), manganese(III) phthalocyanines carrying ethyl 7-oxy-4,8-dimethylcoumarin-3-propanoate moieties
    Koksoy, Baybars
    Aygun, Meryem
    Capkin, Aylin
    Dumludag, Fatih
    Bulut, Mustafa
    JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2018, 22 (1-3) : 121 - 136
  • [42] 1,2,3-Triazole incorporated coumarin carrying metal-free, Zn(II), Mg(II) phthalocyanines: Synthesis, characterization, theoretical studies, photophysical and photochemical properties
    Ozdemir, Mucahit
    Abliatipova, Aziza
    Benian, Sueda
    Yalcin, Bahattin
    Salan, Umit
    Durmus, Mahmut
    Bulut, Mustafa
    JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2020, 403
  • [43] Synthesis, characterization, and investigation of photochemical properties of tetra-substituted zinc phthalocyanines bearing 4-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl moiety with different linker heteroatoms
    Ziminov, Andrey, V
    Sidunets, Yuri A.
    Fundamensky, Vladimir S.
    Gurzhiy, Vladislav V.
    Ramsh, Stanislav M.
    INORGANICA CHIMICA ACTA, 2020, 501
  • [44] Trithiazolyl-1,3,5-triazines bearing decyloxybenzene moieties: synthesis, photophysical and electrochemical properties, and self-assembly behavior
    Kato, Shin-ichiro
    Jin, Satoshi
    Kimura, Terutaka
    Yoshikawa, Naoki
    Nara, Daiki
    Imamura, Kenji
    Shiota, Yoshihito
    Yoshizawa, Kazunari
    Katoono, Ryo
    Yamanobe, Takeshi
    Uehara, Hiroki
    Nakamura, Yosuke
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (19) : 3584 - 3595
  • [45] The synthesis of novel 3-substituted polypyrroles bearing crown-ether moieties and a study of their electrochemical properties
    Guernion, NJL
    Blencowe, A
    Hayes, W
    Lozano-Sanchez, P
    Skaarup, S
    REACTIVE & FUNCTIONAL POLYMERS, 2006, 66 (01): : 201 - 218
  • [46] Synthesis, characterization and electrochemical properties of tetra 7-oxy-3-biphenylcoumarin substituted metal-free, zinc(II), cobalt(II) and indium(III) phthalocyanines
    Gok, Asiye
    Orman, Efe Baturhan
    Salan, Umit
    Ozkaya, Ali Riza
    Bulut, Mustafa
    DYES AND PIGMENTS, 2016, 133 : 311 - 323
  • [47] Identification of (S)-1-(2-(2,4-difluorophenyl)-4-oxothiazolidin-3-yl)-3-(4-((7-(3-(4-ethylpiperazin-1-yl)propoxy)-6-methoxyquinolin-4-yl) oxy)-3,5-difluorophenyl)urea as a potential anti-colorectal cancer agent
    Qi, Baohui
    Wang, Fei
    He, Huan
    Fan, Mengmeng
    Hu, Liping
    Xiong, Li
    Gong, Guowei
    Shi, Shengmin
    Song, Xiaomeng
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2022, 239
  • [48] Synthesis, optical and electrochemical properties of novel meso-triphenylamine-BODIPY dyes with aromatic moieties at 3,5-positions
    Liao, Junxu
    Wang, Yucai
    Xu, Yongjun
    Zhao, Hongbin
    Xiao, Xiaojun
    Yang, Xiaoxi
    TETRAHEDRON, 2015, 71 (31) : 5078 - 5084
  • [49] 3,5-Bis((4′-carboxylbenzyl)oxy) benzoilate-based coordination polymers: their synthesis, structural characterization, and sensing properties
    Huang, Jing-Jing
    Zhang, Xiao
    Huo, Qi-Sheng
    Yu, Jie-Hui
    Xu, Ji-Qing
    INORGANIC CHEMISTRY FRONTIERS, 2016, 3 (03): : 406 - 416
  • [50] Synthesis and characterization of novel quatemized 2, 3-(diethylmethylamino)phenoxy tetrasubstituted Indium and Gallium phthalocyanines and comparison of their antimicrobial and antioxidant properties with different phthalocyanines
    Saki, Neslihan
    Akin, Mustafa
    Atsay, Armagan
    Karaoglu, H. R. Pekbelgin
    Kocak, Makbule Burkut
    INORGANIC CHEMISTRY COMMUNICATIONS, 2018, 95 : 122 - 129
12345