Synthesis and spectral properties of a novel fluorinated triphenylamine derivative
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A novel fluorinated triphenylamine derivative, N,N,N',N'-tetraphenyl-[2', 2, 3', 3, 5', 5, 6', 6octafluoro-p-quater-phenyl]-4,4'-diamine (OFTPA), was designed and synthesized via the palladium-catalyzed Suzuki coupling reaction of 4,4'-di-bromooctafluorobiphenyl with triphenylamine-4-boronic acid (yield: 67%). Its molecular structure was characterized by elemental analysis, melting points, FTIR and 1H NMR spectroscopy, and the main FTIR absorption peaks and 1H NMR spectral bands of the compound were assigned. The energy level structure and photoluminescence properties of OFTPA were investigated by UV-Vis absorption, fluorescence spectroscopy and cyclic voltammetry (CV). The UV-Vis spectroscopy results show that the maximum absorption peak wavelength of OFTPA film is 355 nm, and its optical band gap (E(g)) determined from the obtained absorption spectra is 3.09 eV. The fluorescence spectroscopy results show that OFTPA film can emit intense blue fluorescence with a peak wavelength of 448 nm and a full width at half maximum (FWHM) of 68 nm under UV excitation at 365 nm. So it is a promising candidate for blue electroluminescent materials. The CV results show that the highest occupied molecular orbital (HOMO) energy level and the lowest unoccupied molecular orbital (LUMO) energy level of OFTPA are -5.41 and -2.32 eV, respectively, indicating that it has good hole transport property. The results give a reference to further application to organic optoelectronic device of the target compound.Keywords:
Triphenylamine
HOMO/LUMO
Absorption band
Suzuki reaction
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Crystal (programming language)
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HOMO/LUMO
Monoclinic crystal system
Quantum Efficiency
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9,10-Di(β-naphthyl)anthracene was synthesized by reducing the addition product ofβ-naphthyl- lithium with anthraquinone.Its structure was determined by FTIR and ~1H NMR.Its HOMO,LUMO and luminescence characteristics were studied by UV-Vis absorption spectra,cyclic voltammetry method and fluorescence spectra.In the UV-Vis absorption spectra of ADN,there are two absorption bands,two absorption peaks at 232 nm,260 nm in E band,three peaks at 359 nm,377 nm,398 nm in B band.By the edge of UV absorption 420 nm,we can calculate energy gap of ADN is 2.95 eV. When excited by 398 nm photos,ADN emits blue fluorescence peaked at 426 nm and a full width at half-maximum of 56 nm,showing a very good blue purity.By cyclic voltammetry and the energy gap we can calculate the HOMO energy and LUMO energy of ADN are 5.60 eV and 2.65 eV,respectively.
HOMO/LUMO
Anthraquinones
Absorption edge
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HOMO/LUMO
Quinoline
Pentamer
Oligomer
Acceptor
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Hypsochromic shift
Bathochromic shift
Quinoline
Blueshift
Stokes shift
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4-(5-Methyl-oxadiazole)-phenyl-1,3 butyl diketonate was synthesized via dehydration reaction of 4-acetyl phenylformic ester and hydrazine hydrate,and characterized by IR and 1H NMR.UV-Vis spectra and electrochemical characteristics of the compound were investigated.In addition,the energy gap(Eg) was evaluated to be 2.72 eV from the onset absorption wavelength(λonset/nm) of the UV-Vis spectra,and the energy levels of the highest occupied molecular orbital(HOMO) and the lowest unoccupied molecular orbital(LUMO) were calculated by cyclic voltammetry(CV) and UV-Vis spectrometry.The measurement results of the energy levels indicate that the electron affinity of the compound is higher than that of PBD which is the normal electron-transporting material.Thus it could improve the efficiency of the electroluminescent device when it is used as electron transport layer.
HOMO/LUMO
Hydrazine (antidepressant)
Oxadiazole
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Organic electroluminescent materials 9-(1-naphthyl)-10-(2-naphthyl) anthracene ( α,β-ADN) was synthesized by Suzuki coupling reaction using 9-bromoanthracene,1-naphthyl boronic acid,2-naphthylboronic acid as experiment materials and characterized by FT-IR and 1 H NMR. Electroluminescence properties were studied by UV-Vis absorption spectra and fluorescence spectra. It was shown that the UV-Vis absorption spectra of α,β-AND was composed of two absorption bands,which belonged to E band and B band respectively. It showed two peaks at 232 nm and 262 nm in E band,and three peaks at 359 nm,377 nm,and 398 nm in B band. The absorption edge was 420 nm. When excited by 401 nm photos,the fluorescent emission wave length λmax is 440nm,which means α,β-AND is an excellent blue emitting materials.
Suzuki reaction
Absorption band
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A fluorene–triphenylamine copolymer (PF–TPA) was designed and synthesized under Suzuki coupling reaction conditions in this work. It exhibited a typical electrical conductance switching behavior and non-volatile flash memory effects.
Triphenylamine
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Three novel fluorinated tetraphenylbenzidine derivatives,N,N'-diphenyl-N,N'-bis(2,4-difluorophenyl)-[1,1'-biphenyl]-4,4'-diamine(TFTPB1),N,N'-diphenyl-N,N'-bis(3,4-difluorophenyl)-[1,1'-biphenyl]-4,4'-diamine(TFTPB2) and N,N'-diphenyl-N,N'-bis(3,5-difluorophenyl)-[1,1'-biphenyl]-4,4'-diamine(TFTPB3),were synthesized via palladium-catalyzed Buchwald-Hartwig reaction with the yields of 42%,73% and 76%,respectively.Their molecular structures were characterized by elemental analysis,melting points,FT-IR and 1H-NMR spectrum.Their spectral and electrochemical properties were investigated by UV-Vis absorption,fluorescence spectrum and electrochemical cyclic voltammetry(CV).The results show that,TFTPB1,TFTPB2 and TFTPB3 films have maximum absorption at 337,347 and 346 nm respectively,and they can emit intense blue fluorescence with peak wavelengths at 405,417 and 406 nm,respectively,under ultraviolet excitation at 350 nm.The highest occupied molecular orbital(HOMO) energy levels determined from CV for TFTPB1,TFTPB2 and TFTPB3 are –5.41,–5.47 and –5.59 eV,respectively.These results suggest that the three compounds can be promising candidates for hole transport materials and blue electroluminescent materials.
Biphenyl
HOMO/LUMO
Proton NMR
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Abstract Two pentacene derivatives 1 and 2 were synthesized from the Diels-Alder reactions of furan derivatives with 1,4-benzoquinone. They were characterized by the methods of 1H — nuclear magnetic resonance spectroscopy (1H-NMR), matrix-assisted laser desorption/ionization time of flight mass spectrometry (MALDI-TOF MS), ultraviolet and visible spectrophotometry (UV-VIS), photoluminescence (PL) spectrometry and cyclic voltammetry (CV). The energy gaps of 1 and 2, taken directly from spectroscopic measurements, are broad as 2.72 and 2.46 eV, leading to blue and greenish blue photoluminescence, respectively. The LUMO and HOMO energy levels are −2.77 and −5.49 eV for 1, and −2.91 and −5.37 eV for 2, respectively. The low energy levels make both 1 and 2 good air-stabilities and promising n-type semiconductor candidates for use in organic electronics.
Pentacene
HOMO/LUMO
Organic semiconductor
Organic Electronics
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