42206-02-0

Upstream product

• 56875-26-4 10-methyl-9-phenyl-9,10-dihydroacridine 
• 152071-32-4 methylene blue 
• 24564-52-1 4-(dimethylamino)benzenediazonium tetrafluoroborate 
• 6321-72-8 9-hydroxy-10-methyl-9-phenyl-9,10-dihydroacridine 
• 99354-51-5 9-Deuterio-10-methyl-9-phenylacridan 
• 77816-90-1 9-phenyl-9-ethoxy-10-methylacridine 

Downstream Products

• 56875-26-4 10-methyl-9-phenyl-9,10-dihydroacridine 
• 47072-02-6 1-benzyl-3-carbamoylquinolinium cation 
• 99354-51-5 9-Deuterio-10-methyl-9-phenylacridan 
• 6321-72-8 9-hydroxy-10-methyl-9-phenyl-9,10-dihydroacridine 
• 16183-83-8 1-benzyl-3-carbamoylpyridinium ion 
• 85289-84-5 1-benzyl-3-cyanoquinolinium cation 
• 100667-92-3 9-phenyl-10-methylacridinyl radical 

Relevant academic research and scientific papers

Hydride-Transfer Reaction to a Mononuclear Manganese(III) Iodosylarene Complex

Metal iodosylarene species have received interest because of their potential oxidative power as a catalyst. We present the first example of hydride-transfer reactions to a mononuclear manganese(III) iodosylbenzene complex, [MnIII(TBDAP)(OIPh)(OH)]2+ (1; TBDAP = N,N-di-tert-butyl-2,11-diaza[3.3](2,6)pyridinophane), with dihydronicotinamide adenine dinucleotide (NADH) analogues. Kinetic studies show that hydride-transfer from the NADH analogues to 1 occurs via a proton-coupled electron transfer, followed by a rapid electron transfer.

Simple and modular design platform of bimodal turn-on chemodosimeters for oxophilic metal cations

The selective chemodosimetric behaviour towards oxophilic metal cations of three compounds in one modular platform is explored. Each exhibits turn-on visible colour and emission, while two offer ratiometric emission profiles. The highest performer exhibits 3000-fold enhancement in visible-light emission per equivalent of metal cation.

Excited-state hydroxide ion release from a series of acridinol photobases

The excited-state heterolysis of acridinol-based derivatives leads to the release of the OH-ion and the formation of the corresponding acridinium cations. To evaluate the parameters that control the reaction barriers, the kinetics of excited-state OH-release from a series of acridinol photobases were studied using transient absorption spectroscopy. The rate constants were obtained in three solvents (methanol, butanol, and isobutanol), and the data were modeled using Marcus theory. The intrinsic reorganization energies obtained from these fits were found to correlate well with the solvent reorganization energies calculated using dielectric continuum model, suggesting that the excited-state OH-release occurs along the solvent reaction coordinate. Furthermore, the ability of acridinol photobases to photoinitiate chemical reactions was demonstrated using the Michael reaction between dimethylmalonate and nitrostyrene.

Toward organic photohydrides: Excited-state behavior of 10-methyl-9-phenyl-9,10-dihydroacridine

The excited-state hydride release from 10-methyl-9-phenyl-9,10- dihydroacridine (PhAcrH) was investigated using steady-state and time-resolved UV/vis absorption spectroscopy. Upon excitation, PhAcrH is oxidized to the corresponding iminium ion (PhAcr

Effects of metal ions on physicochemical properties and redox reactivity of phenolates and phenoxyl radicals: Mechanistic insight into hydrogen atom abstraction by phenoxyl radical-metal complexes

Phenolate and phenoxyl radical complexes of a series of alkaline earth metal ions as well as monovalent cations such as Na+ and K+ have been prepared by using 2,4-di-tert-butyl-6-(1,4,7,10-tetraoxa-13-aza-cyclopentadec-13-ylmethyl) phenol (L1H) and 2,4-di-tert-butyl-6-(1,4,7,10,13-pentaoxa-16-aza-cyclo-octadec-16-ylmethyl) phenol (L2H) to examine the effects of the cations on the structure, physicochemical properties and redox reactivity of the phenolate and phenoxyl radical complexes. Crystal structures of the Mg2+- and Ca2+-complexes of L1- as well as the Ca2+- and Sr2+-complexes of L2- were determined by X-ray crystallographic analysis, showing that the crown ether rings in the Ca2+-complexes are significantly distorted from planarity, whereas those in the Mg2+- and Sr2+-complexes are fairly flat. The spectral features (UV-vis) as well as the redox potentials of the phenolate complexes are also influenced by the metal ions, depending on the Lewis acidity of the metal ions. The phenoxyl radical complexes are successfully generated in situ by the oxidation of the phenolate complexes with (NH4)2[Ce4+(NO3)6] (CAN). They exhibited strong absorption bands around 400 nm together with a broad one around 600-900 nm, the latter of which is also affected by the metal ions. The phenoxyl radical-metal complexes are characterized by resonance Raman, ESI-MS, and ESR spectra, and the metal ion effects on those spectroscopic features are also discussed. Stability and reactivity of the phenoxyl radical-metal complexes are significantly different, depending on the type of metal ions. The disproportionation of the phenoxyl radicals is significantly retarded by the electronic repulsion between the metal cation and a generated organic cation (Ln+), leading to stabilization of the radicals. On the other hand, divalent cations decelerate the rate of hydrogen atom abstraction from 10-methyl-9,10-dihydroacridine (AcrH2) and its 9-substituted derivatives (AcrHR) by the phenoxyl radicals. On the basis of primary kinetic deuterium isotope effects and energetic consideration of the electron-transfer step from AcrH2 to the phenoxyl radical-metal complexes, we propose that the hydrogen atom abstraction by the phenoxyl radical-alkaline earth metal complexes proceeds via electron transfer followed by proton transfer.

Spectral Sensitization of Dediazoniation by the 2-Electron-Transfer System meso-Tetraphenylporphinato-dichlorostannate(IV)/10-Methyl-9-phenyl-9.10-dihydro-acridine

The photoreduction of meso-tetraphenylporphinatodichlorostannate(IV) (SnCl2P) by 9-phenyl-10-methyl-9,10-dihydro-acridine (ACH) in 1,2-dichloroethane/acetonitrile 1:1 (v/v) under argon proceeds only with a low quantum yield in spite of the fact that ACH i

Photoreduction of Methyleneblue by the Two-Equivalent Electron Donor N-Methyl-9-phenylacridane and the Use of the System for the Spectrally Sensitized Dediazoniation of p-N,N-Dimethylamino Benzenediazonium Tetrafluoroborate

The photoreduction of methyleneblue by N-methyl-9-phenylacridane (ACH) is studied in acetonitrile by means of flash photolysis and quantum yields.In the first step, due to fast proton shift within the original electron transfer product protonated semi-methyleneblue MBH*+ and the deprotonated donor radical (N-methyl-9-phenylacridanyl radical AC*) are formed with a rate constant of 2*108 M-1s-1.In this radical pair a second electron is transferred very fast from AC* to MBH*+ with a rate constant ke2 ca. 1010s-1 to form leuco-methyleneblue and N-methyl-9-phenyl-acridinium salt (AC+).About 80percent of the two-equivalent reduction product, leuco-methyleneblue, are formed within the first solvent cage during the flash.The maximum quantum yields of photoreduction approach φisc of MB+ as expected for a two-equivalent reduction reaction.The out-of-cage reaction consists of the known disproportionation of the protonated semi-methyleneblue MBH*+ and its reduction by the N-methyl-9-phenylacridanyl radical AC*.From the decay kinetics kred = 3*109 M-1s-1 and kdis=8*108M-1s-1 is derived.The system sensitizers the dediazoniation of p-N,N-dimethylamino benzenediazonium tetrafluoroborate efficiently even at very low diazonium salt concentrations (Φ = 0.6).

MASS SPECTROMETRY OF NITROGEN HETEROCYCLES. 2. CORRELATION OF MASS SPECTROMETRIC FRAGMENTATION PROCESSES AND CHEMICAL AROMATIZATION REACTIONS OF DIHYDROAZINES

The results of mass spectrometric studies of aromatization processes of dihydroazines have been compared with experimental data relative to their chemical oxidation.The results of electron impact induced ionization of dihydroazines can be correlated direc

Hydride transfer reactions. A kinetic study of oxidation of 10-methyl-9-phenylacridan by some ? acceptors and a one-electron oxidant

The kinetics of oxidation of 10-methyl-9-phenylacridan (1(H)) and 9-deuterio-10-methyl-9-phenylacridan (1(D)) to 10-methyl-9-phenylacridinium ion (3) by eight oxidants have been investigated.The oxidants included the ?-acceptors 1,4-benzoquinone (BQ), 7,7,8,8-tetracyanoquinodimethane (TCNQ), p-bromanil (BA), p-chloranil (CA), tetracyanoethylene (TCNE), 2,3-dicyano-1,4-benzoquinone (DCBQ) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in acetonitrile (AN), BQ in 50:50 (v/v) AN-water, and the one-electron oxidant tris(2,2'-bipyridyl)cobalt(III), Co(bipy)33+, in AN.The seven ? acceptors cover a 109-fold range of reactivity from BQ to DDQ and the deuterium kinetic isotope effect varies from 11.9 (BQ in AN) to 5.8 (DDQ).For ? acceptors (BQ, TCNQ, CA, TCNE, and DCBQ) previously investigated with 10-methylacridan (NMA), 1(H) is less reactive than NMA by factors ranging from 9.1 (BQ) to 1.7 x 102 (TCNE).The isotope effects and relative reactivites for the ? acceptor oxidations are most simply explained by a one-step hydride transfer mechanism.

PHOTODISSOCIATION OF DERIVATIVES OF N-METHYL-9-PHENYLACRIDAN

Photodissociation of N-methyl-)-phenylacridan derivatives in methanol, ethanol, propanol, 2-propanol, acetonitrile, and methylene chloride takes place nonadiabatically, i.e., the reaction product (cation) is formed immediately in the ground state.The quantum yields and rate constants of photodissociation were determined.The N-methyl-9-phenylacridinium which forms undergoes dark solvolysis with a first-order rate constant, which depends linearly on the polarity of the solvent (1/ε).