Synthesis, structures and photophysical properties of boron fluorine derivatives based on pyridine/1,8-naphthyridine

被引：13
作者：
Li, Zhensheng [1 ,2 ]
Lv, Xiaojun [1 ,2 ]
Chen, Yong [1 ,2 ]
Fu, Wen-Fu [1 ,2 ,3 ]
机构：
[1] Chinese Acad Sci, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China
[2] Chinese Acad Sci, HKU Joint Lab New Mat, Tech Inst Phys & Chem, Beijing 100190, Peoples R China
[3] Yunnan Normal Univ, Coll Chem & Engn, Kunming 650092, Peoples R China
来源：
DYES AND PIGMENTS | 2014年 / 105卷
关键词：
Boron-fluorine compound; 1,8-Naphthyridine; Structures; Solid-state emission; Fluorescence quantum yield; pH sensor; LARGE STOKES SHIFT; NAPHTHYRIDINE-BF2; COMPLEXES; SPECTROSCOPIC PROPERTIES; DYES; EMISSION; BODIPYS;
D O I：
10.1016/j.dyepig.2014.01.022
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Three boron fluorine complexes B1-B3 containing pyridine/1,8-naphthyridine were synthesized and structurally characterized. Compounds B1 and B2 exhibited strong fluorescence in solution and solid state. The solvent-dependent luminous properties and large Stokes shift in solution could be explained by intramolecular charge transfer, which is confirmed by time-dependent density functional theory calculation. The absolute quantum yield of B1 in powder form reached 0.48 because of inhibiting planar pi...pi stacking. Single-crystal X-ray diffraction analyses of B1 and B2 revealed that weak intermolecular C H...F and H...pi interactions hinder further stacking of pi...pi dimers, consequently preventing aggregation-induced quenching. Complex 113, composed of boron-dipyrromethene and 1,8-naphthyridine fluorophore, had potential applications as a pH ratiometric fluorescent sensor. (c) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：157 / 162
页数：6
相关论文
共 30 条
  • [1] The Smallest and One of the Brightest. Efficient Preparation and Optical Description of the Parent Borondipyrromethene System
    Arroyo, Ismael J.
    Hu, Rongrong
    Merino, Gabriel
    Tang, Ben Zhong
    Pena-Cabrera, Eduardo
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) : 5719 - 5722
  • [2] meso-Pyridyl BODIPYs with tunable chemical, optical and electrochemical properties
    Bartelmess, Juergen
    Weare, Walter W.
    Latortue, Narah
    Duong, Christina
    Jones, Daniel S.
    [J]. NEW JOURNAL OF CHEMISTRY, 2013, 37 (09) : 2663 - 2668
  • [3] 4,4′-Difluoro-4-bora-3a,4a-diaza-s-indacenes (BODIPYs) as components of novel light active materials
    Benstead, Michael
    Mehl, Georg H.
    Boyle, Ross W.
    [J]. TETRAHEDRON, 2011, 67 (20) : 3573 - 3601
  • [4] Fluorescent indicators based on BODIPY
    Boens, Noel
    Leen, Volker
    Dehaen, Wim
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (03) : 1130 - 1172
  • [5] Conformation impact on spectral properties of bis(5,7-dimethyl-1,8-naphthyridin-2-yl)amine and its ZnII complex
    Chen, Yong
    Fu, Wen-Fu
    Li, Jun-Li
    Zhao, Xi-Juan
    On, Xue-Mei
    [J]. NEW JOURNAL OF CHEMISTRY, 2007, 31 (10) : 1785 - 1788
  • [6] 8-Hydroxyquinoline-Substituted Boron-Dipyrromethene Compounds: Synthesis, Structure, and OFF-ON-OFF Type of pH-Sensing Properties
    Chen, Yuting
    Wang, Hailong
    Wan, Liang
    Bian, Yongzhong
    Jiang, Jianzhuang
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (10) : 3774 - 3781
  • [7] Influence of selectivity on the supramolecular polymerization of AB-type polymers capable of both A•A and A•B interactions
    de Greef, Tom F. A.
    Ercolani, Gianfranco
    Ligthart, G. B. W. L.
    Meijer, E. W.
    Sijbesma, Rint P.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (41) : 13755 - 13764
  • [8] Hemilability of 2-(1H-imidazol-2-yl)pyridine and 2-(oxazol-2-yl)pyridine ligands: Imidazole and oxazole ring Lewis basicity, Ni(II)/Pd(II) complex structures and spectra
    Eseola, Abiodun O.
    Li, Wen
    Adeyemi, Olalere G.
    Obi-Egbedi, Nelson O.
    Woods, Joseph A. O.
    [J]. POLYHEDRON, 2010, 29 (08) : 1891 - 1901
  • [9] Synthesis and characterization of nickel(II) complexes bearing 2-(imidazol-2-yl)pyridines or 2-(pyridin-2-yl)phenanthroimidazoles/oxazoles and their polymerization of norbornene
    Eseola, Abiodun O.
    Zhang, Min
    Xiang, Jun-Feng
    Zuo, Weiwei
    Li, Yan
    Woods, Joseph A. O.
    Sun, Wen-Hua
    [J]. INORGANICA CHIMICA ACTA, 2010, 363 (09) : 1970 - 1978
  • [10] Frisch M, 2015, Gaussian 09, revision a 02
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