Circularly Polarized Luminescence of Boronic Acid-Derived Salicylidenehydrazone Complexes Containing Chiral Boron as Stereogenic Unit

被引:31
|
作者
Jimenez, Vicente G. [1 ]
Santos, Fabio M. F. [2 ]
Castro-Fernandez, Silvia [1 ]
Cuerva, Juan M. [1 ]
Gois, Pedro M. P. [2 ]
Pischel, Uwe [3 ,4 ]
Campana, Araceli G. [1 ]
机构
[1] Univ Granada, Dept Organ Chem, Campus Univ Fuentenueva, E-18071 Granada, Spain
[2] Univ Lisbon, Res Inst Med iMed ULisboa, Fac Pharm, Ave Prof Gama Pinto, P-1649003 Lisbon, Portugal
[3] Univ Huelva, CIQSO Ctr Res Sustainable Chem, Campus El Carmen S-N, E-21071 Huelva, Spain
[4] Univ Huelva, Dept Chem, Campus El Carmen S-N, E-21071 Huelva, Spain
来源
JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 22期
关键词
CHIROPTICAL PROPERTIES; ENANTIOSELECTIVE SYNTHESIS; ORGANIC-MOLECULES; FLUORESCENT; BODIPY; DYES; ABSORPTION; EFFICIENT; HELICENE; DESIGN;
D O I
10.1021/acs.joc.8b01844
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Racemic mixtures of boronic acid-derived salicylidenehydrazone (BASHY) complexes were enantiomerically resolved. The chiroptical properties of the stereoisomers, containing an asymmetric boron as the only stereogenic unit, are translated into mirror-imaged electronic circular dichroism spectra and circularly polarized luminescence (CPL, dissymmetry factors of 3-5 x 10(-4)) is observed. The spectral position of the CPL emission is determined by the push-pull character of the dye. These features expand the functional scope of the brightly emitting BASHY dye platform.
引用
收藏
页码:14057 / 14062
页数:6
相关论文
共 50 条
  • [1] Planar chiral boron difluoride complexes showing circularly polarized luminescence
    Chen, Chun-Hua
    Zheng, Wen-Hua
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (23) : 6622 - 6627
  • [2] Cyanine-Like Boronic Acid-Derived Salicylidenehydrazone Complexes (Cy-BASHY) for Bioimaging Applications
    Santos, Fabio M. F.
    Dominguez, Zoe
    Fernandes, Joao P. L.
    Parente Carvalho, Catia
    Collado, Daniel
    Perez-Inestrosa, Ezequiel
    Pinto, Maria V.
    Fernandes, Adelaide
    Arteaga, Jesus F.
    Pischel, Uwe
    Gois, Pedro M. P.
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (62) : 14064 - 14069
  • [4] Aggregation-amplified circularly polarized luminescence from axial chiral boron difluoride complexes
    Zhiyong Jiang
    Xiaoqing Wang
    Jianping Ma
    Zhipeng Liu
    Science China(Chemistry), 2019, (03) : 355 - 362
  • [5] Aggregation-amplified circularly polarized luminescence from axial chiral boron difluoride complexes
    Jiang, Zhiyong
    Wang, Xiaoqing
    Ma, Jianping
    Liu, Zhipeng
    SCIENCE CHINA-CHEMISTRY, 2019, 62 (03) : 355 - 362
  • [6] Aggregation-amplified circularly polarized luminescence from axial chiral boron difluoride complexes
    Zhiyong Jiang
    Xiaoqing Wang
    Jianping Ma
    Zhipeng Liu
    Science China Chemistry, 2019, 62 : 355 - 362
  • [7] Aggregation-amplified circularly polarized luminescence from axial chiral boron difluoride complexes
    Zhiyong Jiang
    Xiaoqing Wang
    Jianping Ma
    Zhipeng Liu
    Science China(Chemistry), 2019, 62 (03) : 355 - 362
  • [8] Highly Efficient Energy Transfer Cassettes by Assembly of Boronic Acid Derived Salicylidenehydrazone Complexes
    Santos, Fabio M. F.
    Dominguez, Zoe
    Alcaide, Maria M.
    Matos, Ana I.
    Florindo, Helena F.
    Candeias, Nuno R.
    Gois, Pedro M. P.
    Pischel, Uwe
    CHEMPHOTOCHEM, 2018, 2 (12): : 1038 - 1045
  • [9] Circularly Polarized Luminescence of Aluminum Complexes for Chiral Sensing of Amino Acid and Amino Alcohol
    Jin, Qingxian
    Wang, Fulin
    Chen, Shuyu
    Zhou, Liming
    Jiang, Hejin
    Zhang, Li
    Liu, Minghua
    CHEMISTRY-AN ASIAN JOURNAL, 2020, 15 (02) : 319 - 324
  • [10] Lanthanide complexes as chiral probes exploiting circularly polarized luminescence
    Carr, Rachel
    Evans, Nicholas H.
    Parker, David
    CHEMICAL SOCIETY REVIEWS, 2012, 41 (23) : 7673 - 7686