An acac-BODIPY dye as a reversible "ON-OFF-ON" fluorescent sensor for Cu2+ and S2- ions based on displacement approach

被引:25
作者
More, Ankush B. [1 ]
Mula, Soumyaditya [2 ]
Thakare, Shrikant [1 ]
Chakraborty, Saikat [2 ]
Ray, Alok K. [3 ]
Sekar, Nagaiyan [1 ]
Chattopadhyay, Subrata [2 ]
机构
[1] Inst Chem Technol, Dept Dyestuff Technol, Bombay 400019, Maharashtra, India
[2] Bhabha Atom Res Ctr, Bioorgan Div, Bombay 400085, Maharashtra, India
[3] Bhabha Atom Res Ctr, Laser & Plasma Technol Div, Bombay 400085, Maharashtra, India
关键词
BODIPY; Cu2+; ions; sensor; S2-; anions; AQUEOUS-SOLUTION; SULFIDE ANION; SENSITIVE CHEMOSENSOR; CU(II) IONS; PROBE; RECOGNITION; COPPER(II); ENHANCEMENT; SELECTIVITY; STRATEGIES;
D O I
10.1016/j.jlumin.2017.06.005
中图分类号
O43 [光学];
学科分类号
070207 ; 0803 ;
摘要
An ON-OFF-ON type BODIPY-based fluorescent sensor bearing acetylacetone (acne) moiety was synthesized and characterized. The molecule revealed ON-OFF type fluorescence behaviour with high selectivity toward Cu2+ Iion without any interference from other cations. Once combined with Cu2+, it displayed high specificity for S2- anion with in situ recovery of the quenched fluorescence, based on the displacement approach. DFT studies of the dye and its Cu2+ complex indicated an efficient relocation of electron charge density from dye to Cu2+ in LUMO rationalizing the selective quenching of dye fluorescence upon association with Cu2+ ion. The acacconjugated BODIPY dye was also effective to detect the designated ions in live cells.
引用
收藏
页码:476 / 484
页数:9
相关论文
共 77 条
[1]  
[Anonymous], SOLVENT EXTRACTION M
[2]  
[Anonymous], COMPREHENSIVE COORDI
[3]   Copper [J].
Barceloux, DG .
JOURNAL OF TOXICOLOGY-CLINICAL TOXICOLOGY, 1999, 37 (02) :217-230
[4]   Neurodegenerative diseases and oxidative stress [J].
Barnham, KJ ;
Masters, CL ;
Bush, AI .
NATURE REVIEWS DRUG DISCOVERY, 2004, 3 (03) :205-214
[5]   Copper-induced modifications of the trophic relations in riverine algal-bacterial biofilms [J].
Barranguet, C ;
van den Ende, FP ;
Rutgers, M ;
Breure, AM ;
Greijdanus, M ;
Sinke, JJ ;
Admiraal, W .
ENVIRONMENTAL TOXICOLOGY AND CHEMISTRY, 2003, 22 (06) :1340-1349
[6]   A SPECTROPHOTOMETRIC INVESTIGATION OF THE INTERACTION OF IODINE WITH AROMATIC HYDROCARBONS [J].
BENESI, HA ;
HILDEBRAND, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (08) :2703-2707
[7]   Design, synthesis and photophysical studies of dipyrromethene-based materials: insights into their applications in organic photovoltaic devices [J].
Bessette, Andre ;
Hanan, Garry S. .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (10) :3342-3405
[8]   Fluorescent indicators based on BODIPY [J].
Boens, Noel ;
Leen, Volker ;
Dehaen, Wim .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (03) :1130-1172
[9]   Unraveling the mechanisms involved in motor neuron degeneration in ALS [J].
Bruijn, LI ;
Miller, TM ;
Cleveland, DW .
ANNUAL REVIEW OF NEUROSCIENCE, 2004, 27 :723-749
[10]   Luminescent sensors and switches in the early 21st century [J].
Callan, JF ;
de Silva, AP ;
Magri, DC .
TETRAHEDRON, 2005, 61 (36) :8551-8588