Synthesis and Fluorescence Properties of Thiazole-Boron Complexes Bearing a β-Ketoiminate Ligand

被引:130
作者
Kubota, Yasuhiro [1 ]
Tanaka, Syunki [1 ]
Funabiki, Kazumasa [1 ]
Matsui, Masaki [1 ]
机构
[1] Gifu Univ, Fac Engn, Dept Mat Sci & Technol, Gifu 5011193, Japan
关键词
AGGREGATION-INDUCED EMISSION; PHOTOPHYSICAL PROPERTIES; FLUORINE COMPLEXES; CRYSTAL-STRUCTURES; STOKES SHIFT; BODIPY DYES; FLUOROPHORES; DERIVATIVES; ENHANCEMENT; INTENSITY;
D O I
10.1021/ol302179r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel fluorescent dyes, thiazole boron complexes bearing beta-ketoiminate ligands, have been synthesized, and their fluorescence properties were investigated. The BF2 complexes showed a pronounced aggregation-induced emission enhancement effect because of the restriction of C-Ph intramolecular rotation. The BPh2 complexes showed higher fluorescence quantum yields than the corresponding BF2 complexes, both in solution and in the solid state.
引用
收藏
页码:4682 / 4685
页数:4
相关论文
共 64 条
[1]   High Stokes Shift Anilido-Pyridine Boron Difluoride Dyes [J].
Araneda, Juan F. ;
Piers, Warren E. ;
Heyne, Belinda ;
Parvez, Masood ;
McDonald, Robert .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (51) :12214-12217
[2]   Difluoro-boron-triaza-anthracene: a laser dye in the blue region. Theoretical simulation of alternative difluoro-boron-diaza-aromatic systems [J].
Banuelos, Jorge ;
Lopez Arbeloa, Fernando ;
Martinez, Virginia ;
Liras, Marta ;
Costela, Angel ;
Garcia Moreno, Inmaculada ;
Lopez Arbeloa, Inigo .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2011, 13 (08) :3437-3445
[3]   DIRECT MEASUREMENTS OF TETRAPHENYLETHYLENE TORSIONAL MOTION BY PICOSECOND SPECTROSCOPY [J].
BARBARA, PF ;
RAND, SD ;
RENTZEPIS, PM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (09) :2156-2162
[4]   4,4′-Difluoro-4-bora-3a,4a-diaza-s-indacenes (BODIPYs) as components of novel light active materials [J].
Benstead, Michael ;
Mehl, Georg H. ;
Boyle, Ross W. .
TETRAHEDRON, 2011, 67 (20) :3573-3601
[5]   Matrix dependence of light emission from TCNQ adducts [J].
Bloor, D ;
Kagawa, Y ;
Szablewski, M ;
Ravi, M ;
Clark, SJ ;
Cross, GH ;
Pålsson, LO ;
Beeby, A ;
Parmer, C ;
Rumbles, G .
JOURNAL OF MATERIALS CHEMISTRY, 2001, 11 (12) :3053-3062
[6]   STERIC HINDRANCE TO PLANARITY IN DYE MOLECULES [J].
BROOKER, LGS ;
WHITE, FL ;
SPRAGUE, RH ;
DENT, SG ;
VANZANDT, G .
CHEMICAL REVIEWS, 1947, 41 (02) :325-351
[7]   Selective photodynamic therapy based on aggregation-induced emission enhancement of fluorescent organic nanoparticles [J].
Chang, Cheng-Chung ;
Hsieh, Meng-Chieh ;
Lin, Jung-Chih ;
Chang, Ta-Chau .
BIOMATERIALS, 2012, 33 (03) :897-906
[8]   Naphthalene-based fluorophores: Synthesis characterization, and photophysical properties [J].
Feng, Jinwu ;
Chen, Xiaopeng ;
Han, Qingchuan ;
Wang, Hongbo ;
Lu, Ping ;
Wang, Yanguang .
JOURNAL OF LUMINESCENCE, 2011, 131 (12) :2775-2783
[9]   Novel Fluorescent Dyes with Fused Perylene Tetracarboxlic Diimide and BODIPY Analogue Structures [J].
Feng, Junqian ;
Liang, Baolong ;
Wang, Delou ;
Xue, Lin ;
Li, Xiyou .
ORGANIC LETTERS, 2008, 10 (20) :4437-4440
[10]   Near-infrared dyes and fluorophores based on diketopyrrolopyrroles [J].
Fischer, Georg M. ;
Ehlers, Andreas R. ;
Zumbusch, Andreas ;
Daltrozzo, Ewald .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (20) :3750-3753