1165-91-9Relevant academic research and scientific papers
Quenching effect of some heavy metal ions on the fast peroxyoxalate-chemiluminescence of 1-(dansylamidopropyl)-1-aza-4,7,10-trithiacyclododecane as a novel fluorophore
Shamsipur, Mojtaba,Zargoosh, Kiomars,Hosseini, Seyed Morteza,Caltagirone, Claudia,Lippolis, Vito
, p. 205 - 209 (2009)
The fast chemiluminescence (CL) arising from the reaction of bis(2,4,6-trichlorophenyl)oxalate (TCPO) with hydrogen peroxide in the presence of 1-(dansylamidopropyl)-1-aza-4,7,10-trithiacyclododecane (L) as a novel fluorophore, and imidazole as catalyst, has been studied in ethyl acetate solution. The relationships between the chemiluminescence intensity and concentrations of TCPO, imidazole, hydrogen peroxide and L are reported. In the presence of imidazole as catalyst, the entire CL signal was completed in less than 3 s. The quenching effect of Cu2+, Pb2+, Cd2+, Hg2+ and Ag+ ions on the chemiluminescent system was investigated, the resulting Stern-Volmer plots were obtained and the KQ values were calculated. It was found that the quenching effect of metal ions on the chemiluminescence of L decreases in the order Cu2+ > Pb2+ > Cd2+ > Hg2+ > Ag+.
Chemiluminescence characteristics of Furan derivatives as blue fluorescers in peroxyoxalate-hydrogen peroxide system
Chaichi,Azizi,Heidarpour,Aalijanpour,Qandalee
, p. 1209 - 1216 (2012)
Furan derivatives (synthesized and purified in organic laboratories) are a great interest as fluorescent emitters for peroxyoxalate chemiluminescence. Reaction of peroxyoxalates such as bis-(2,4,6-trichloro-phenyl) oxalate with H2O2 can transfer energy to fluorophore via formation of dioxetanedione intermediate. Furan derivatives used as a novel fluorescer in this study which produces a blue light in the chemiluminescence systems. The relationship between the chemiluminescence intensity and concentrations of TCPO, sodium salicylate, hydrogen peroxide and the fluorescer has been investigated. The linear ranges for Furan derivatives were 0.25-5×10-4 M and 0.1-5×10-4 M (A and B compounds, respectively). Kinetic parameters for the peroxyoxalate-chemiluminescence were also calculated from the computer fitting of the corresponding chemiluminescence intensity/time profiles. Springer Science+Business Media, LLC 2012.
The Hammett correlation between distyrylbenzene substituents and chemiluminescence efficiency providing various ρ-values for peroxyoxalate chemiluminescence of several oxalates
Maruyama, Takayuki,Narita, Susumu,Motoyoshiya, Jiro
, p. 222 - 231 (2013/03/13)
Peroxyoxalate chemiluminescence (PO-CL) was investigated using eight oxalates with various phenol moieties and the distyrylbenzene (DSB) fluorophores with various substituents. The ρ-values in the Hammett correlation between the substituent constants (σp+) of the DSBs and the singlet chemiexcitation yields (ΦS) for the PO-CL reactions varied from -0.50 to -1.01 depending on the oxalate structure, and the reactive oxalates tended to afford the higher absolute ρ-values but with a few exceptions. Based on the CIEEL mechanism, these experimental observations suggest that the aryloxy groups still remain in the 1,2-dioxetanones (DOTs), which are the postulated high-energy intermediates, and control the electronic properties of DOTs as electron-acceptors. The LUMO energies of the DOTs calculated by the ab initio method with a B3LYP/6-31g(d) basis set reveal that the lower the DOT-LUMO energies, the higher the absolute ρ-values were provided for the corresponding oxalates, as predicted by the frontier molecular orbital (FMO) theory. Thus, the chemical species interacting with the DSBs would be not unitary and will be DOTs.
Control of peroxyoxalate chemiluminescence by nitrogen-containing ligand quenching: Turning off and on by ligand-metal ion host-guest interactions
Maruyama, Takayuki,Fujie, Yasuyuki,Oya, Noriyuki,Hosaka, Eisuke,Kanazawa, Aki,Tanaka, Daisuke,Hattori, Yoshiyuki,Motoyoshiya, Jiro
experimental part, p. 6927 - 6933 (2011/10/02)
The control of peroxyoxalate chemiluminescence (PO-CL) by the coordination of nitrogen-containing ligands and metal cations was investigated. Turning the CL off and on was done by PO-CL using 15-monoazacrown-5-tethered anthracene and alkali metal ions. CL quenching and regeneration was also observed in the separated molecular system of 15-monoazacrown-5 and the fluorophores. CL quenching by a number of ligands bearing dipicolylamino groups was evaluated by these PO-CL reactions and found to be closely related to their oxidation potentials, which is dependent on the Weller rate law for electron exchange and this provides strong support for the existence of the CIEEL PO-CL process. When Zn2+ or Cu2+ are added to the PO-CL system quenched by the ligand, N-[2-(2,2′-dipicolylamino)ethyl]aniline, CL was turned on because the electron donating ability of the ligands was modulated. This was controlled by the coordination of the studied metal ions and, therefore, this system results in CL because of host-guest interactions.
Synthesis and identification of organosoluble polyamides bearing a triaryl imidazole pendent: Thermal, photophysical, chemiluminescent, and electrochemical characterization with a modified carbon nanotube electrode
Ghaemy,Amini Nasab
experimental part, p. 306 - 313 (2011/11/12)
A novel monomer containing a triaryl imidazole pendent group was successfully synthesized by nucleophilic substitution of bisphenol A with 2-(2-chloro-5-nitrophenyl)-4,5-diphenyl-1H-imidazole (I). A series of new polyamides (PAs) with inherent viscosities of 0.95-1.2 dL/g was prepared by direct polycondensation of the diamine with various dicarboxylic acids. These PAs were readily soluble in many organic solvents and gave tough and flexible films by solution casting. These PAs exhibited Tgs between 189 °C and 252 °C, and 10% weight loss temperatures in excess of 400 °C with up to 68% char yield at 600 °C in air. All of the PAs emitted a greenish-yellow light in dilute THF solution, with photoluminescence (PL) quantum yields in the range of 10-25%. The chemiluminescent activity and electrochemical oxidation of the PAs were also investigated.
Aryl oxalate derivatives as convenient precursors for generation of aryloxyl radicals
Lahti, Paul M.,Modarelli, David A.,Rossitto, Frank C.,Inceli, Ahmet Levent,Ichimura, Andrew S.,Ivatury, Shyamala
, p. 1730 - 1738 (2007/10/03)
The use of aryloxy oxalyl chlorides (AOCs), aryloxy oxalyl tert-butyl peroxides (AOBs), and diaryl oxalates (DAOs) for unimolecular generation of phenoxyl-based radicals under solution and rigid matrix conditions is described. AOCs are usable for photochemical generation of phenoxyl radicals, but are only conveniently stable as precursors when 2,6-di-tert-butylated derivatives are used. AOBs may be used as thermal precursors to aryloxyl radicals, since they typically decompose within 2-3 h at 60-85 °C to give phenols. 1H-NMR solution kinetic studies find that ΔH? = 31 kcal/mol, and ΔS? = +3.4 cal/mol-K for decomposition of phenoxyoxalyl tert-butyl peroxide, consistent with substantial concertedness in peroxide bond cleavage. AOBs and the more stable DAOs are also convenient photochemical phenoxyl radical precursors. AOBs yield phenoxyl radicals more readily by photolysis than do corresponding DAOs, but the DAOs have fewer side reactions that can quench the product phenoxyl radicals.
