Two novel aggregation-induced emission active coumarin-based Schiff bases and their applications in cell imaging

Xiao, Haiyan; Chen, Kun; Cui, Dandan; Jiang, Nannan; Yin, Geping; Wang, Jie; Wang, Ruiyong

doi:10.1039/c3nj01557b

Cited by 66 publications

(34 citation statements)

References 48 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The applications and properties of coumarin scaffold have remarkably wide boundaries. Coumarin-based compounds have been exploited in numerous research and industrial sectors, as active pharmaceutical ingredients, pesticides, fragrances, dyes for several purposes from laser technology to organic photoredox catalysis, cell imaging, photocleavable protecting groups and fluorescent biological probes [6,[218][219][220][221][222][223][224][225]. In the following paragraphs, the most recent applications associated with the photophysical properties of coumarins have been reviewed.…”

Section: Coumarins Photopropertiesmentioning

confidence: 99%

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

Annunziata

Pinna

Dallavalle

et al. 2020

IJMS

255

156

View full text Add to dashboard Cite

Privileged structures have been widely used as an effective template for the research and discovery of high value chemicals. Coumarin is a simple scaffold widespread in Nature and it can be found in a considerable number of plants as well as in some fungi and bacteria. In the last years, these natural compounds have been gaining an increasing attention from the scientific community for their wide range of biological activities, mainly due to their ability to interact with diverse enzymes and receptors in living organisms. In addition, coumarin nucleus has proved to be easily synthetized and decorated, giving the possibility of designing new coumarin-based compounds and investigating their potential in the treatment of various diseases. The versatility of coumarin scaffold finds applications not only in medicinal chemistry but also in the agrochemical field as well as in the cosmetic and fragrances industry. This review is intended to be a critical overview on coumarins, comprehensive of natural sources, metabolites, biological evaluations and synthetic approaches.

show abstract

Section: Coumarins Photopropertiesmentioning

confidence: 99%

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

Annunziata

Pinna

Dallavalle

et al. 2020

IJMS

255

156

View full text Add to dashboard Cite

show abstract

“…More highly efficiency, stable and multi-colored organic lightemitting materials need to be developed [2,3]. A series of aggregation induced enhanced emission (AIEE) compounds have been reported by the Tang et al [4,5], and more of these AIEE compounds have been found including styrene acrylic instead of nitrile [6,7], salicylaldehyde [8][9][10] and coumarinbased Schiff bases [11] etc. Our group has also reported AIEE compounds based on phenothiazine [12] or naphthalene [13] as the structural units.…”

Section: Introductionmentioning

confidence: 99%

Characterization of the Aggregation-Induced Enhanced Emission of N,N′-bis(4-methoxysalicylide)benzene-1,4-diamine

Wu¹,

Xu²,

Zeng³

et al. 2015

J Fluoresc

View full text Add to dashboard Cite

N,N'-bis(4-methoxysalicylide)benzene-1,4-diamine (S1) was synthesized from 4-methoxysalicylaldehyde and p-phenylenediamine and it was found to exhibit interesting aggregation-induced emission enhancement (AIEE) characteristics. In aprotic solvent, S1 displayed very weak fluorescence, whilst strong emission was observed when in protic solvent. The morphology characteristics and luminescent properties of S1 were determined from the fluorescence and UV absorption spectra, SEM, fluorescence microscope and grading analysis. Analysis of the single crystal diffraction data infers that the intramolecular hydrogen bonding constitutes to a coplanar structure and orderly packing in aggregated state, which in turn hinders intramolecular C-N single bond rotation. Given that the three benzene rings formed a large plane conjugated structure, the fluorescence emission was significantly enhanced. The absolute fluorescence quantum yield and fluorescence lifetime also showed that radiation transition was effectively enhanced in the aggregated state. Moreover, the AIEE behavior of S1 suggests there is a potential application in the fluorescence sensing of some volatile organic solvents.

show abstract

“…[11,12] This approach has been successfully appliedt ot he synthesis of luminescent square tubes, [13] andt ot he detection of small amountso fhydrazine in water. [14] Salicylaldehydea zine derivatives, with AIEE properties, have also been used for cellular imaging [15,16] and as molecular probesf or the detection of thiols in live cells. [17] The study of the solid-stateo rganization of one benzophenone azine derivative providedi nsight into the importance of polymorphs,a sa changei nt he crystals tructurel ead to ac hange in the emission wavelength, induced and controlled by the application of externals timuli.…”

Section: Introductionmentioning

confidence: 99%

Tunable Color of Aggregation‐Induced Emission Enhancement in a Family of Hydrogen‐Bonded Azines and Schiff Bases

Guieu

Cardona

Rocha

et al. 2018

Chemistry A European J

View full text Add to dashboard Cite

A simple synthesis strategy afforded a family of hydrogen-bonded azines and Schiff-bases. Although in dilute solution these dyes are faint light emitters, all exhibit bright luminescence upon aggregation. Changing the peripheral substituents from electron donating to electron withdrawing allows emission fine-tuning in a range from bluish-green to orange-red. The crystal structures of the materials reveal that the restriction of intramolecular rotations is the main mechanism for the aggregation-induced emission enhancement properties.

show abstract

Two novel aggregation-induced emission active coumarin-based Schiff bases and their applications in cell imaging

Abstract: Two coumarin-based AIE-active compounds emitting ESIPT fluorescence with large Stocks-shifts were applied to cell imaging.

Cited by 66 publications

References 48 publications

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

Characterization of the Aggregation-Induced Enhanced Emission of N,N′-bis(4-methoxysalicylide)benzene-1,4-diamine

Tunable Color of Aggregation‐Induced Emission Enhancement in a Family of Hydrogen‐Bonded Azines and Schiff Bases

Contact Info

Product

Resources

About