Synthesis and Photophysical Characterization of Novel ESIPT Triazinyl-Benzazole Derivatives

被引:1
|
作者
Grasel, Fabio S. [1 ,2 ]
Barreto, Fabiano [3 ]
Jank, Louise [1 ,3 ]
Stefani, Valter [1 ]
机构
[1] Univ Fed Rio Grande do Sul, Inst Quim, BR-91501970 Porto Alegre, RS, Brazil
[2] Pontificia Univ Catolica Rio Grande do Sul, Programa Posgrad Engn & Tecnol Mat, BR-90619900 Porto Alegre, RS, Brazil
[3] Minist Agr Pecuaria & Abastecimento, Lab Nacl Agr LANAGRO RS, BR-91780580 Porto Alegre, RS, Brazil
关键词
benzazole; cyanuric chloride; ESIPT; reactive dye; large Stokes' shift; fluorescence; INTRAMOLECULAR PROTON-TRANSFER; ACID-DERIVATIVES; REACTIVE DYES; POLYAMIDOAMINE DENDRIMERS; FLUORESCENT; STATE; MECHANISM; OXIDATION; EMISSION; LIGANDS;
D O I
10.5935/0103-5053.20150148
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this work, the synthesis, characterization and photophysical study of new derivatives of triazinyl-benzazoles with fluorescence by excited-state intramolecular proton transfer (ESIPT) are presented. It regards the synthesis of cyanuric chloride with different 2-(2'-hydroxyphenyl) benzazoles, two quite attractive groups from the synthetic and technological point of view. These new compounds have several potential applications such as biological markers and new photoluminescent materials. The derivatives were characterized by H-1 and C-13 nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopy (FTIR), high-resolution mass spectrometry (HRMS), UV-Vis absorption and fluorescence emission. The dyes are fluorescent by an excited-state ESIPT in the blue-orange region, with a large Stokes' shift.
引用
收藏
页码:2496 / 2506
页数:11
相关论文
共 50 条
  • [1] Synthesis, Characterization and Photophysical Properties of ESIPT Reactive Triazine Derivatives
    Kuplich, Marcelo D.
    Grasel, Fabio S.
    Campo, Leandra F.
    Rodembusch, Fabiano S.
    Stefani, Valter
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2012, 23 (01) : 25 - U352
  • [2] Synthesis, Characterization and Photophysical Properties of Novel Azole Derivatives
    Saleem, Muhammad
    Lee, Ki Hwan
    JOURNAL OF FLUORESCENCE, 2015, 25 (02) : 217 - 226
  • [3] Synthesis, Characterization and Photophysical Properties of Novel Azole Derivatives
    Muhammad Saleem
    Ki Hwan Lee
    Journal of Fluorescence, 2015, 25 : 217 - 226
  • [4] Synthesis and photophysical properties of novel succinimidyl benzazole derivatives, evaluated by Candida albicans ATCC 10231 fluorescent staining
    dos Santos, Rosane Catarina
    da Silva Faleiro, Nalva Vivian
    Campo, Leandra Franciscato
    Scroferneker, Maria Lucia
    Corbellini, Valeriano Antonio
    Rodembusch, Fabiano Severo
    Stefani, Valter
    TETRAHEDRON LETTERS, 2011, 52 (23) : 3048 - 3053
  • [5] Novel ESIPT fluorescent benzazolyl-4-quinolones: Synthesis, spectroscopic characterization and photophysical properties
    Lins, Gisele O. W.
    Campo, Leandra F.
    Rodembusch, Fabiano S.
    Stefani, Valter
    DYES AND PIGMENTS, 2010, 84 (01) : 114 - 120
  • [6] Synthesis, characterization and photophysical properties of novel tetrasubstituted phthalocyaninato zinc derivatives
    Liu, Qing-He
    Fu, Qiang
    Yang, Jin
    Ma, Ji-Cheng
    Li, Wei-Li
    Wang, Xue
    JOURNAL OF MOLECULAR STRUCTURE, 2010, 963 (01) : 41 - 44
  • [7] Synthesis, characterization and photophysical properties of novel thiazole substituted pyridine derivatives
    Suryawanshi, Manjusha
    Gujar, Varsha
    Ottoor, Divya
    Bobade, Vivek
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2019, 58 (12): : 1361 - 1374
  • [8] Water-Soluble Benzazole Dyes Fluorescent by ESIPT: Structural Characterization, Photophysical Properties and Its Application as a Probe for Direct Staining of Helminths
    Barros, Helio L.
    Marques, Sandra M. T.
    Stefani, Valter
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2019, 30 (03) : 509 - 521
  • [9] Synthesis and photophysical study of novel 3-triazinyl- and 3-pyridinyl-substituted coumarins
    Potapova, Anastasia P.
    Taniya, Olga S.
    Valieva, Maria I.
    Khalymbadzha, Igor A.
    Sharapov, Ainur D.
    Starnovskaya, Ekaterina S.
    Kopchuk, Dmitry S.
    Gaviko, Vasiliy S.
    Novikov, Alexander S.
    Kalinichev, Alexey A.
    Fatykhov, Ramil F.
    OPTICAL MATERIALS, 2025, 158
  • [10] Substituent effect on ESIPT mechanisms and photophysical properties of HBT derivatives
    Yang, Yunfan
    Luo, Xiao
    Ma, Fengcai
    Li, Yongqing
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2021, 250