60974-92-7

Usage

Uses

Used in Imaging Applications:
9,10-BIS(DIETHYLPHOSPHONOMETHYL)ANTHRACENE is used as a synthetic building block for the development of compounds with imaging applications. Its unique chemical structure allows for the creation of molecules that can be utilized in various imaging techniques, enhancing the visualization and detection of specific biological processes or structures.
In the field of medical imaging, 9,10-BIS(DIETHYLPHOSPHONOMETHYL)ANTHRACENE can be used as a component in the synthesis of contrast agents, which are essential for improving the visibility of internal organs and tissues in imaging modalities such as X-ray, MRI, and CT scans. 9,10-BIS(DIETHYLPHOSPHONOMETHYL)ANTHRACENE's properties may also make it suitable for the development of fluorescent probes or markers for use in fluorescence microscopy and other related imaging techniques.
Additionally, 9,10-BIS(DIETHYLPHOSPHONOMETHYL)ANTHRACENE may find applications in the field of molecular imaging, where it can be used to develop targeted imaging agents that can specifically bind to and visualize molecular targets, such as receptors or enzymes, that are overexpressed in certain diseases or conditions. This can aid in the early detection, diagnosis, and monitoring of various diseases, as well as in the evaluation of therapeutic responses to treatment.

InChI:InChI=1/C24H32O6P2/c1-5-27-31(25,28-6-2)17-23-19-13-9-11-15-21(19)24(22-16-12-10-14-20(22)23)18-32(26,29-7-3)30-8-4/h9-16H,5-8,17-18H2,1-4H3

Upstream product

• 120-12-7 anthracene 
• 78-40-0 triethyl phosphate 
• 10387-13-0 9,1-bis(chloromethyl)anthracene 
• 50-00-0 formaldehyd 
• 122-52-1 triethyl phosphite 
• 34373-96-1 9,10-dibromomethylanthracene 

Downstream Products

• 1412103-08-2 9,10-bis((E)-2-(pyridin-2-yl)vinyl)anthracene 
• 1443249-13-5 C₃₆H₃₄O₂ 
• 1443249-15-7 C₆₂H₈₆O₂ 
• 136384-82-2 4,4'-(1E,1'E)-2,2'-(anthracene-9,10-diyl)bis(ethene-2,1-diyl)dibenzonitrile 
• 113308-38-6 9,10‐bis((E)‐2‐(pyridin‐4‐yl)vinyl)anthracene 
• 1429664-95-8 9,10-bis((E)-2-(pyridin-3-yl)vinyl)anthracene 
• 1434302-05-2 C₅₄H₃₆I₄N₂ 
• 1073118-45-2 9,10-bis(4-(dodecyloxy)styryl)anthracene 

Relevant academic research and scientific papers

9,10-Bis((Z)-2-phenyl-2-(pyridin-2-yl)vinyl)anthracene: Aggregation-induced emission, mechanochromic luminescence, and reversible volatile acids-amines switching

Pyridine-containing luminophores have been attracting much attention due to pyridine functions in carrier transport and cation complexation. Here we prepared a butterfly-like molecule 9,10-bis(2-phenyl-2-(pyridin-2-yl)vinyl)anthracene (PyVA) for developing new multifunctional dyes. The multiple rotatable aryl groups enabled PyVA to exhibit a strong aggregation-induced emission effect, and the seriously twisted butterfly-like backbone rendered the solid weak intermolecular π-π interactions and mechanofluorochromism. Quantum chemical calculations indicated that protonation of the pyridyl units could narrow the band gap of PyVA, and X-ray crystallography revealed that PyVA molecules packed in a Z configuration in which the pyridyl units adopted a more twisted conformation with lone N-electron pairs stabilized by intra- and intermolecular CH···N and CH···π interactions. It was observed that both fluorescent crystalline and amorphous PyVA solids could sense volatile acids with a remarkably red-shifted emission, but the amorphous state was more sensitive. Moreover, the acidichromic PyVA solid could further sense volatile amines, and this alternative pH sensitive chromic process was reversible and applicable to fluorescence patterning.

Luminescent switching and structural transition through multiple external stimuli based on organic molecular polymorphs

Investigations on the relationship between multi-stimuli responsive luminescent properties and aggregation structures of polymorphs play a crucial role in developing organic multi-stimuli responsive luminescent (OMSRL) materials. Herein, we reported two p

Solvatochromism, Reversible Chromism and Self-Assembly Effects of Heteroatom-Assisted Aggregation-Induced Enhanced Emission (AIEE) Compounds

Two compounds, 9,10-bis[2-(quinolyl)vinyl]anthracene (BQVA) and 9,10-bis[2-(naphthalen-2-yl)vinyl]anthracene (BNVA), have been synthesised and investigated. Both of them have aggregation-induced enhanced emission (AIEE) properties. Heteroatom-assisted BQVA shows solvatochromism, reversible chromism properties and self-assembly effects. When increasing the solvent polarities, the green solution of BQVA turns to orange with a redshift of the fluorescence emission wavelengths from λ=527 to 565 nm. Notably, BQVA exhibits reversible chromism properties, including mechano- and thermochromism. The as-prepared BQVA powders show green fluorescence (λem=525 nm) and the colour can turn into orange (λem=573 nm) after grinding. Interestingly, the orange colour can return at high temperature. Based on these reversible chromism properties, a simple and convenient erasable board has been designed. Different from BQVA, non-heteroatom-assisted BNVA has no clear chromic processes. The results obtained from XRD, differential scanning calorimetry, single-crystal analysis and theoretical calculations indicate that the chromic processes depend on the heteroatoms in BQVA. Additionally, BQVA also exhibits excellent self-assembly effects in different solvents. Homogeneous nanospheres are formed in mixtures of tetrahydrofuran and water, which are then doped into silica nanoparticles and treated with 3-aminopropyltriethoxysilane to give amino-functionalised nanoparticles (BQVA-AFNPs). The BQVA-AFNPs could be used to stain protein markers in polyacrylamide gel electrophoresis.

Plasmon-Enhanced Fluorescent Sensor based on Aggregation-Induced Emission for the Study of Protein Conformational Transformation

The alteration in protein conformation not only affects the performance of its biological functions, but also leads to a variety of protein-mediated diseases. Developing a sensitive strategy for protein detection and monitoring its conformation changes is of great significance for the diagnosis and treatment of protein conformation diseases. Herein, a plasmon-enhanced fluorescence (PEF) sensor is developed, based on an aggregation-induced emission (AIE) molecule to monitor conformational changes in protein, using prion protein as a model. Three anthracene derivatives with AIE characteristics are synthesized and a water-miscible sulfonate salt of 9,10-bis(2-(6-sulfonaphthalen-2-yl)vinyl)anthracene (BSNVA) is selected to construct the PEF–AIE sensor. The sensor is nearly non-emissive when it is mixed with cellular prion protein while emits fluorescence when mixed with disease-associated prion protein (PrPSc). The kinetic process of conformational conversion can be monitored through the fluorescence changes of the PEF–AIE sensor. By right of the amplified fluorescence signal, this PEF–AIE sensor can achieve a detection limit 10 pM lower than the traditional AIE probe and exhibit a good performance in human serum sample. Furthermore, molecular docking simulations suggest that BSNVA tends to dock in the β-sheet structure of PrP by hydrophobic interaction between BSNVA and the exposed hydrophobic residues.

Efficient red organic light-emitting diodes using 2-(2-(4-Pentylbicyclo[2. 2.2]octan-1-yl)-6-(2-(1,1,7-trimethyl-7-triphenysiliyllethyl-1,2,3,5,6, 7-hexahydropyrido[3,2,1-ij]quinolin-9-yl)vinyl)-4Hpyran- 4-ylidene)malononitrile as a fluorescent red emitter

The authors have demonstrated red organic light-emitting diodes (OLEDs) using a new fluorescent red emitter, 2-(2-(4-pentylbicyclo[2.2.2]octan-1-yl)-6- (2-(1,1,7-trimethyl- 7-triphenysiliyllethyl-1,2,3,5,6,7-hexahydropyrido[3,2,1- ij]quinolin-9-yl)vinyl)-4Hpyran- 4-ylidene)malononitrile (DCJTPSO), achieved the maximum external quantum efficiency (EQE) of 2.06%, current efficiency (CE) of 3.83 cd/A, and Commision Internationale De L'Eclairage (CIEx,y) coordinates of (0.58, 0.40) at 0.029 mA/cm2 in comparison with control device using 4-(dicyanomethylene)-2-tert-butyl- 6-(1,1,7, 7-tetramethyljulolidin-4-yl-vinyl)- 4H-pyran which showed the maximum EQE of 1.07%, CE of 1.41 cd/A and CIEx,y coordinates of (0.61, 0.38) at 0.11 mA/cm2. This result showed that the high performance of red device using DCJTPSO showed easier electron trapping directly on the emitter molecule. Copyright Taylor & Francis Group, LLC.

Solid-state fluorescence properties and reversible piezochromic luminescence of aggregation-induced emission-active 9,10-bis[(9,9- dialkylfluorene-2-yl)vinyl]anthracenes

In this work, we have synthesized 9,10-bis[(9,9-dialkylfluorene-2-yl)vinyl] anthracene derivatives (FLA-Cn) with propyl, pentyl, and dodecyl side chains to investigate their fluorescence properties. The results show that FLA-Cn exhibit not only an aggregation-induced emission effect but also reversible piezofluorochromic (PFC) behaviour. Interestingly, the fluorescence emission and grinding-induced spectral shifts (ΔλPFC) of FLA-Cn solids are alkyl length-dependent: the longer alkyl-containing FLA-Cn solids show more blue-shifted emission and larger ΔλPFC. Moreover, the fluorescence emission of ground FLA-C12 solid can recover spontaneously at room temperature, Powder wide-angle X-ray diffraction and differential scanning calorimetry experiments reveal that the transformation between crystalline and amorphous states under various external stimuli is responsible for the PFC behaviour, and the spontaneous recovering emission of amorphized FLA-C12 solid is ascribed to its low cold-crystallization temperature. This work demonstrates once again the accessibility of tuning the solid-state optical properties of organic fluorophores by combining the simple alternation of molecular chemical structure and the physical change of aggregate morphology under external stimuli.

Synthesis of dopant with phenothiazine moiety and polymer electroluminescence device properties

(N-2-ethylhexyyl-3(6)-phenothiazinylene vinylene-co-9, 10-anthrylene vinyleone), KPD-1, as a new low molecular weight dopant was synthesized. Poly(1,12-dodecanedioxy-2-methoxy-1,4-phenylene-1,2-ethenylene-1, 1′-biphenyl-4,4′-ylene-1,2-ethenylene-3-methoxy-1,4-phenylene), /Poly(BFMP12AV)/, as a matrix polymer was also prepared by Honer-Emmons condensation. Single- and multi-layered PLKDs were fabricated with a mixture of dopant/matrix polymer as an emissive layer. The effect of dopant/matrix polymer and device structures on the energy transfer and electro-optical properties of doped PLKDs was discussed in terms of emission color changes and luminescence efficiency of doped PLEDs. Copyright Taylor & Francis Inc.

A cationic on-off fluorescent sensor with AIE properties for heparin and protamine detection

In this research, a distyryl-anthracene derivative (DSAI) with two quaternary ammonium groups was synthesized. It emitted strong yellow-green fluorescence after aggregating with heparin through electrostatic attraction. In the presence of protamine, the fluorescence of DSAI remarkably quenched because of the greater affinity between heparin and protamine. Based on the change of fluorescence signal, a highly sensitive and selective method is successfully constructed to detect heparin and protamine. The DSAI sensor toward heparin showed a broad linear range (0.1 to 1.1 μg mL?1) and a low detection limit (down to 5.64 ng mL?1). The linear detection for protamine was in a wide range (0.1 to 1.7 μg mL?1) with the detection limit of 5.20 ng mL?1. Moreover, DSAI was successfully applied to detect heparin and protamine in complicated goat serum samples with satisfactory results. This simple and ultrasensitive biosensor has potential applications in diagnostics, therapeutics and biological research.

Influence of alkyl length on properties of piezofluorochromic aggregation induced emission compounds derived from 9,10-bis[(N-alkylphenothiazin-3-yl) vinyl]anthracene

Three 9,10-bis[(N-alkylphenothiazin-3-yl)vinyl]anthracene derivatives with different propyl, hexyl, and dodecyl side chains (AnPh3, AnPh 6, and AnPh12) were synthesized and confirmed by standard spectroscopic methods. All of the compounds exhibited obvious aggregation induced emission (AIE) and piezofluorochromic (PFC) properties. The PFC behaviors were investigated and showed that proportional alkyl-length dependent relationship existed not only in the ground states of the compounds, but also in the melted states compared with the fumed states of the compounds. The PFC mechanism was explored and ascribed to the crystalline-amorphous phase transformation. More importantly, these derivatives showed reversible significant PFC properties and reproducibility in various states including fumed, ground, annealed, and melted states, making them promising stimuli-responsive and smart luminescent materials for pressure-sensors, information-recording, and light-emitting device applications.

12b,24b-Diborahexabenzo[a,c,fg,l,n,qr]pentacene: A Low-LUMO Boron-Doped Polycyclic Aromatic Hydrocarbon

Herein we devise and execute a new synthesis of a pristine boron-doped nanographene. Our target boron-doped nanographene was designed based on DFT calculations to possess a low LUMO energy level and a narrow band gap derived from its precise geometry and B-doping arrangement. Our synthesis of this target, a doubly B-doped hexabenzopentacene (B2-HBP), employs six net C?H borylations of an alkene, comprising consecutive hydroboration/electrophilic borylation/dehydrogenation and BBr3/AlCl3/2,6-dichloropyridine-mediated C?H borylation steps. As predicted by our calculations, B2-HBP absorbs strongly in the visible region and emits in the NIR up to 1150 nm in o-dichlorobenzene solutions. Furthermore, B2-HBP possesses a very low LUMO level, showing two reversible reductions at ?1.00 V and ?1.17 V vs. Fc+/Fc. Our methodology is surprisingly selective despite its implementation of unfunctionalized precursors and offers a new approach to the synthesis of pristine B-doped polycyclic aromatic hydrocarbons.