14678-71-8Relevant academic research and scientific papers
Deformative transition of the menschutkin reaction and helical atropisomers in a congested polyheterocyclic system
Chang, Yung-Yu,Ho, Tse-Lok,Chung, Wen-Sheng
, p. 9970 - 9978 (2014)
A 4,7-phenanthroline polycyclic 1A designed for probing the limits of the Menschutkin reaction was synthesized in a six-step sequence. The rotational barrier of the phenyl ring nearby the N-methyl group in rac-2A was estimated to be 18.1 kcal/mol from VT-NMR experiments, making them a new type of helical atropisomer. The methylation rate constants of 9 and 1A with MeI was found to be 2.22 × 10-4 and 9.62 × 10-6 s-1 mol-1 L, respectively; thus, the formation rate of (P/M)-2A is one of the slowest rates ever reported for a Menschutkin reaction. The N-methyl protons in (P/M)-2A exhibit a significant upfield shift (Δδ 1.0 ppm) in its 1H NMR, compared to those without a nearby phenyl, indicating a strong CH-π interaction is involved. Conformational flexibility in dipyridylethene 9 is clearly shown by its complexation with BH3 to form helical atropisomers (P,P/M,M)-10. The pKa values of the conjugate acids of 1A and 9 in acetonitrile were determined to be 4.65 and 5.07, respectively, which are much smaller compared to that of pyridine 14a (pKa = 12.33), implying that the basicity, nucleophilicity, and amine alkylation rates of 1A and 9 are markedly decreased by the severe steric hindrance of the flanking phenyl rings in the polyheterocycles.
2,5-Diphenyl-3,4-bis(2-pyridyl)cyclopenta-2,4-dien-1-one as a redox-active chelating ligand
Siemeling, Ulrich,Scheppelmann, Imke,Heinze, Juergen,Neumann, Beate,Stammler, Anja,Stammler, Hans-Georg
, p. 5661 - 5670 (2004)
2,5-Diphenyl-3,4-bis(2-pyridyl)cyclopenta-2,4-dien-1-one (1), a close relative of tetraphenylcyclopentadienone, is a new ligand platform for use in redox switches and sensors. Compound 1 acts as a molecular electrochemical sensor towards a range of divale
Tetraaryl Cyclopentadienones: Experimental and Theoretical Insights into Negative Solvatochromism and Electrochemistry
Meitinger, Nicolas,Mengele, Alexander K.,Witas, Kamil,Kupfer, Stephan,Rau, Sven,Nauroozi, Djawed
, p. 6555 - 6562 (2020/10/02)
The synthesis of a series of tetraaryl cyclopentadienones comprising different substitution patterns is reported. Their photophysical and electrochemical properties are investigated by UV/Vis spectroscopy and cyclic voltammetry as well as by supporting quantum chemical simulations and reveal a distinct effect of substituents on the redox behavior of the molecules as well as the absorption properties of this class of compounds. While electrochemical data display a shift in reduction potential of up to 200 mV between the differently substituted cyclopentadienones, their photophysical investigations in differently polar solvents suggest a negative solvatochromic effect, although protic solvents induce a bathochromic shift. Crystal structure analyses of some derivatives confirm similarity with related cyclopentadienones while providing insight into intermolecular C–H···O and C–H···π interactions in the solid state.
Double bridged μ2-Halide Cu (II) complexes for the electrocatalytic reduction of CO2
Sadehvand, Maryam,Amiri, Ahmad,Tirani, Farzaneh Fadaei,Gu, Jun,Schenk-Jo?, Kurt
, (2019/08/22)
Two dicopper (II) complexes of general formula [CuLX2]2 {L = 2, 5-diphenyl-3, 4(2-pyridyl) cyclopenta-2, 4-dien-1-one, X = Cl (1) or Br (2)} have been synthesized and characterized by elemental analysis, IR, UV–Vis spectroscopic meth
Highly sensitive and selective fluorescent sensor for Zn 2+/Cu2+ and new approach for sensing Cu2+ by central metal displacement
Li, Zhanxian,Zhang, Lifeng,Wang, Lina,Guo, Yongkai,Cai, Lianheng,Yu, Mingming,Wei, Liuhe
supporting information; experimental part, p. 5798 - 5800 (2011/06/25)
An "off-on" Zn2+ and "on-off" Cu 2+ fluorescent chemosensor C was designed and synthesized. The binding of C and Zn2+/Cu2+ is chemically reversible by the addition of EDTA disodium solution; moreover, the fluore
