Asymmetric anthracene-fused BODIPY dye with large Stokes shift: Synthesis, photophysical properties and bioimaging

Yang, Liutao; Liu, Ying; Zhou, Xiangge; Wu, Yue; Ma, Chunping; Liu, Wei; Zhang, Chun

doi:10.1016/j.dyepig.2015.11.028

Cited by 31 publications

(13 citation statements)

References 71 publications

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“…2,[10][11][12][13][14][15][16][17][18] By reviewing the synthetic routes of luminescent organoboron compounds, numerous methods have been carried out by conventional methods, for example simple reflux to open-flask can be isolated tetracoordinated fluorescent Boron compounds derived from Schiff bases and Ph 2 BOH or PhB(OH) 2 . 5,[19][20][21] However, when starting materials of Boron are air-sensitive such as BPh 3 , 22-24 BF 3 (OEt 2 ), [25][26][27][28][29][30] BBr 3 , 31,32 and (Mes) 2 BF (Mes = 2,4,6-Me 3 C 6 H 2 ) 33 the synthesis must be carried out in special conditions due to their high toxicity and reactivity (Scheme 1). For example, it has been reported the synthesis of derived from quinolate, [34][35][36][37][38] smaragdyrins, 39 difluoroboron, 40,41 BODIPYs, [42][43][44] and three-coordinated molecules using Schlenk line, [45][46][47] with reaction time ranging from 2 to 18 hours, and other multi-step synthesis , which takes around 5 days.…”

Section: Synthesis Of Luminescent Organoboron Materialsmentioning

confidence: 99%

Recent advances of synthesis of Boron derivatives and their applications in bioimaging

Muñoz‐Flores

Molina‐Paredes

Lara‐Cerón

et al. 2018

IJAMB

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The increasing interest in the luminescent boron materials is due to their potential application in diverse areas such as solar cells, optoelectronic devices, and biological imaging materials. Continuous search for the compounds with better properties, luminescent organoboron materials have been gaining more importance, especially in the development of new technologies and novel techniques for bioimaging, which is a powerful tool to analyze the cellular organelles with important value into the cell biology and medical research. Synthesis, properties, and applications of luminescent boron compounds and their application in bioimaging are reviewed.

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Section: Synthesis Of Luminescent Organoboron Materialsmentioning

confidence: 99%

Recent advances of synthesis of Boron derivatives and their applications in bioimaging

Muñoz‐Flores

Molina‐Paredes

Lara‐Cerón

et al. 2018

IJAMB

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“…Research on the synthesis and characterization of new fused rings systems for OSCs have been reported [13] as well as the role of fused ring molecules (aromatic and antiaromatic) in catalysis and in biology is well described in literature [14][15][16][17][18][19]. In this context, it is worthy to mention that molecules with indacene core present several studies concerning electronic interaction between two metals centers, as it is possible to obtain two equivalent active sites in this type of molecule [17][18][19].…”

Section: Introductionmentioning

confidence: 98%

Theoretical study of aromatic-antiaromatic pairs as material in organic solar cells of double light harvesting

Martínez

Schott

Chávez

et al. 2016

Chemical Physics Letters

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“…In the recent decade, fluorescent organoboron compounds have gained tremendous attention due to different and interesting applications such as optoelectronic devices, sensors, security inks, and fluorescent bioimaging (FBI) . The cellular biology and biomedicine are quite interesting about the advances in fluorescence imaging technologies to identify organelle and cellular abnormalities which are associated with severe diseases and disabilities .…”

Section: Introductionmentioning

confidence: 99%

Organoboron Schiff bases as cell‐staining fluorescent probes: Synthesis, Chemio‐photophysical characterization, DFT, and X‐ray structures

Ibarra-Rodríguez

Muñoz‐Flores

Gómez-Treviño

et al. 2019

Applied Organom Chemis

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The fluorescence imaging technologies are becoming the most powerful and noninvasive diagnostic tools in cellular biology and modern medicine where abnormal cell arrangements are associated with diseases. Thus, these techniques require new fluorescent dyes with excellent chemical, physical, and photophysical properties. A series of four new Boron Schiff bases (1–4) has been prepared by condensation between phenylboronic acid with the corresponding ligand. The compounds were characterized by NMR (1H, 13C, and 11B), UV/vis, fluorescence spectroscopy, and high‐resolution mass spectrometry. The crystal structures of three compounds showed tetracoordinated Boron atoms with semiplanar skeleton ligands. Interesting organoboron response to viscosity on their fluorescence (Φ: more than 3‐fold). Additionally, compounds 1 and 2 were found to serve as a fluorescent dye for cell imaging (B16F10, CaCo, and A‐431 cells) since it has the capability to rapidly accumulate within the cells and gave bright green fluorescence, it showed low cytotoxicity activity and high photostability in solution. Additionally, the compounds have also been investigated using DFT.

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Asymmetric anthracene-fused BODIPY dye with large Stokes shift: Synthesis, photophysical properties and bioimaging

Cited by 31 publications

References 71 publications

Recent advances of synthesis of Boron derivatives and their applications in bioimaging

Recent advances of synthesis of Boron derivatives and their applications in bioimaging

Theoretical study of aromatic-antiaromatic pairs as material in organic solar cells of double light harvesting

Organoboron Schiff bases as cell‐staining fluorescent probes: Synthesis, Chemio‐photophysical characterization, DFT, and X‐ray structures

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