1552-40-5Relevant academic research and scientific papers
Pd-Catalyzed Cross-Coupling of Organostibines with Styrenes to Give Unsymmetric (E)-Stilbenes and (1 E,3 E)-1,4-Diarylbuta-1,3-dienes and Fluorescence Properties of the Products
Zhang, Zhao,Zhang, Dejiang,Zhu, Longzhi,Zeng, Dishu,Kambe, Nobuaki,Qiu, Renhua
supporting information, p. 5317 - 5322 (2021/06/28)
A general and effective palladium-catalyzed cross-coupling of organostibines with styrenes to give (E)-olefins was disclosed. By the use of an organostibine reagent, this method can produce unsymmetric (E)-1,2-diarylethylenes and (1E,3E)-1,4-diarylbuta-1,3-dienes in good yields with high E/Z selectivity and good functional group tolerance. Resveratrol and DMU-212 were synthesized in high yield. The protocol can be extended to the synthesis of (1E,3E,5E)-1,6-diphenylhexa-1,3,5-triene in 40% yield. Products 5e, 5f, and 7a showed good photoluminescence quantum yields ranging from 72 to 99%.
Effect of substituents and conjugated chain length on the UV spectra of α,ω-di-substituted phenyl polyenes
Cao, Chenzhong,Zhu, Yun,Chen, Guanfan
, p. 834 - 839 (2013/10/01)
A series of α,ω-di-substituted phenyl polyenes, p-X-Ph(CH = CH)nPh-p-Y (n = 1, 2, or 3) were synthesized, and their ultraviolet (UV) absorption maximum wavelength were determined. The correlation between molecular structure and the maximum wavelength energy (wavenumber/cm -1) was carried out. The results show that the maximum wavelength energy of the title compounds is mainly affected by both substituent excited-state parameters and maximum wavelength energy of the parent molecule. However, the two influence factors are not independent, and the action of substituent is governed by the parent molecular absorption energy. In the case of the compounds containing NO2 or NH2 groups, the influence of interaction of polarity parameters on the maximum wavelength energy must also be considered. In addition, the exploration was also made for the quantifying correlation of UV absorption maximum wavelength energy with the conjugated polarizability potential CPP replacing the parent molecular absorption energy. And the results indicate that the equation with CPP parameters is more accurate and convenient. Copyright 2013 John Wiley & Sons, Ltd. For the α,ω-di-substituted phenyl polyenes, p-X-Ph(CH = CH)nPh-p-Y (n = 1, 2, or 3), their ultraviolet absorption maximum wavelength energy (wavenumber/cm-1) was mainly affected by both substituent excited-state parameters and maximum wavelength energy of the parent molecule. However, the two influence factors are not independent, and the action of substituent is governed by the parent molecular absorption energy. Copyright
Synthesis and characterization of fluorescent ligands for the norepinephrine transporter: Potential neuroblastoma imaging agents
Hadrich, Dirk,Berthold, Frank,Steckhan, Eberhard,B?nisch, Heinz
, p. 3101 - 3108 (2007/10/03)
Radiolabeled m-iodobenzylguanidine (MIBG) is a tumor-seeking radioactive drug used in the diagnosis and treatment of pheochromocytomas and neuroblastomas. It is transported into the tumor cells by the neuronal norepinephrine (NE) transporter (NET) which is expressed in almost all neuroblastoma cells. Here, we describe the synthesis and some pharmacological properties of a series of fluorescent compounds structurally related to the NET substrate, MIBG, or to the NET inhibitors, (-)-(2R,3S)-cocaine and nisoxetine. Three of 10 synthesized fluorescent compounds, 1-(1- naphthylmethyl)guanidinium sulfate (1), 1-[2-(dibenz[b,f]azepin-5- yl)ethyl]guanidinium sulfate (2), and (2R,3S)-2β-ethoxycarbonyl-3β-tropanyl 5-(dimethylamino)naphthalene-1-sulfonate (6), exhibited high affinity (IC50 about 50 nM) for the NET. The nisoxetine derivatives 8 (rac-N-[(3- methylamino-1-phenyl)propyl]-5-(dimethylamino)-1-naphthalene-sulfonamide) and 9 (rac-4-[(3-methylamino-1-phenyl)propyl]amino-7-nitro-2,1,3-benzoxadiazole) and especially the guanidine derivative 4 (1-[4-(4-phenyl-l,3- butadienyl)benzyl]guanidinium sulfate) which are characterized by intermediate affinity for the NET (IC50 370-850 nM) caused significant and nisoxetine-sensitive cell fluorescence. At least the guanidine derivative 4 might represent a potentially useful agent for imaging of neuroblastoma cells.
Free Enthalpy Dependence of Free Radical Yield of Photoincuced Electron Transfer in Acetonitrile
Kikuchi, Koichi,Takahashi, Yasutake,Hoshi, Masato,Niwa, Taeko,Katagiri, Tomoharu,Miyashi, Tsutomu
, p. 2378 - 2381 (2007/10/02)
The free enthalpy dependence of the free-radical yield ΦR of the electron-transfer (ET) fluorescence quenching was studied in acetonitrile by using anthracenecarbonitriles as the electron-accepting fluorescer and 1,4-diphenyl-1,3-butadienes as the electron-donating quencher. ΦR decreases, passes through a minimum, increases with increase of ΔGf, the free enthalpy change involved in the actual ET process, and then suddenly falls when ΔGf goes beyond -0.25 eV.Switchover of the quenching mechanism was suggested for the ET fluorescence quenching: The radical pairs are exclusively produced by the full ET in the encounter state bet ween the fluorescer and the quencher when ΔGf is smaller than -0.4 eV, but in contrast through the partial ET, i.e., the exciplex formation as the primary quenching products when ΔGf is larger than -0.4 eV.
