Synthesis, Luminescent Properties of aza-Boron-Diquinomethene Difluoride Complexes and Their Application for Fluorescent Security Inks

Gu, Long; Li, Rui; Hong, Shiming; Wang, Qiang; Song, Guangliang; Zhu, Xiaolin; Yuan, Shidong

doi:10.1007/s10895-015-1727-6

Cited by 8 publications

(3 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Luminescent aromatic and heteroaromatic organic molecules are widely used in many modern applications, including organic light emitting diodes (OLEDs), − solar cells, , bioimaging, security, , and sensing. , In particular, organic molecules are prime candidates for OLED applications with the photoluminescence quantum yields reaching 100%. , By reduction of nonradiative decay, most of the excited states that form in a device can emit, thus enhancing their performance.…”

Section: Introductionmentioning

confidence: 99%

Bond Rotations and Heteroatom Effects in Donor–Acceptor–Donor Molecules: Implications for Thermally Activated Delayed Fluorescence and Room Temperature Phosphorescence

et al. 2018

View full text Add to dashboard Cite

New thermally activated delayed fluorescence (TADF) blue emitter molecules based on the known donor−acceptor−donor (D−A−D)type TADF molecule, 2,7-bis(9,9-dimethylacridin-10-yl)-9,9-dimethylthioxanthene-S,S-dioxide (DDMA-TXO2), are reported. The motivation for the present investigation is via the use of rational molecular design, based on DDMA-TXO2, to elevate the organic light emitting diode (OLED) performance and obtain deeper blue color coordinates. To achieve this goal, the strength of the donor (D) unit and acceptor (A) units have been tuned with methyl substituents. The methyl functionality on the acceptor was also expected to modulate the D−A torsion angle in order to obtain a blue shift in the electroluminescence. The effect of regioisomeric structures has also been investigated. Herein, we report the photophysical, electrochemical, and single-crystal X-ray crystallography data to assist with the successful OLED design. The methyl substituents on the DDMA-TXO2 framework have profound effects on the photophysics and color coordinates of the emitters. The weak electron-donating methyl groups alter the redox properties of the D and A units and consequently affect the singlet and triplet levels but not the energy gap (ΔE ST ). By systematically manipulating all of the aforementioned factors, devices have been obtained with acceptor-substituted III with a maximum external quantum efficiency of 22.6% and Commission Internationale de l'Ećlairage coordinates of (0.15, 0.18) at 1000 cd m −2 .

show abstract

Section: Introductionmentioning

confidence: 99%

Bond Rotations and Heteroatom Effects in Donor–Acceptor–Donor Molecules: Implications for Thermally Activated Delayed Fluorescence and Room Temperature Phosphorescence

et al. 2018

View full text Add to dashboard Cite

show abstract

“…In the past several years, various fluorescent materials have been explored in the preparation of water-based anti-counterfeit ink, such as organic fluorescent dyes [ 4 , 5 ], rare-earth luminescent materials [ 6 , 7 , 8 ], carbon dots [ 9 , 10 , 11 , 12 ], organic polymers [ 13 , 14 ] etc. Compared with other fluorescent materials, organic fluorescent dyes have the advantages of easy access to raw materials, more variety, bright colors and a low cost.…”

Section: Introductionmentioning

confidence: 99%

Preparation of 1, 3, 6, 8-Pyrenesulfonic Acid Tetrasodium Salt Dye-Doped Silica Nanoparticles and Their Application in Water-Based Anti-Counterfeit Ink

Jiao

Zhang

2020

Materials

View full text Add to dashboard Cite

In order to improve the luminescent stability of water-based anti-counterfeit ink, a new fluorescent material is prepared by doping dye into silica nanoparticles. Water soluble anionic dye 1, 3, 6, 8-pyrenesulfonic acid sodium salt (PTSA) is selected as the dopant. In this work, PTSA is successfully trapped into silica nanoparticles (SiNPs) by the reverse microemulsion method using cationic polyelectrolyte poly (dimethyl diallyl ammonium chloride; PDADMAC) as a bridge. The UV absorption spectra, fluorescence emission spectra and fluorescent decay curves are used to describe the luminescent properties of the PTSA-doped silica nanoparticles (PTSA-SiNPs). In addition, the as-prepared PTSA-SiNPs and polyurethane waterborne emulsion are used to prepare water-based anti-counterfeit ink, and fluorescent patterns are successfully printed through screen-printing. The samples printed by the ink exhibit desirable fluorescence properties, heat stability, robust photostability, and a fluorescent anti-counterfeit effect, which makes the PTSA-SiNPs promising luminescent materials for anti-counterfeit applications.

show abstract

“…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

View full text Add to dashboard Cite

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.

show abstract

Synthesis, Luminescent Properties of aza-Boron-Diquinomethene Difluoride Complexes and Their Application for Fluorescent Security Inks

Cited by 8 publications

References 31 publications

Bond Rotations and Heteroatom Effects in Donor–Acceptor–Donor Molecules: Implications for Thermally Activated Delayed Fluorescence and Room Temperature Phosphorescence

Bond Rotations and Heteroatom Effects in Donor–Acceptor–Donor Molecules: Implications for Thermally Activated Delayed Fluorescence and Room Temperature Phosphorescence

Preparation of 1, 3, 6, 8-Pyrenesulfonic Acid Tetrasodium Salt Dye-Doped Silica Nanoparticles and Their Application in Water-Based Anti-Counterfeit Ink

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

Contact Info

Product

Resources

About