77902-89-7Relevant academic research and scientific papers
Taming the Reactivity of Phosphiranium Salts: Site-Selective C-Centered Ring Opening for Direct Synthesis of Phosphinoethylamines
Alayrac, Carole,Botella, Clément,Comesse, Sébastien,Dalla, Vincent,Gasnot, Julien,Gaumont, Annie-Claude,Lakhdar, Sami,Taillier, Catherine
, p. 11769 - 11773 (2020)
Advances in the field of phosphorus chemistry are documented, by revealing the synthetic utility of previously underutilized quaternary phosphiranium salts (QPrS) as three-chain-atom electrophilic building blocks. Notably, control of their challenging C-centered electrophilicity is disclosed with an expedient synthesis of tertiary β-anilino phosphines as a proof-of-concept.
Photocatalytic hydrogen evolution using 9-phenyl-10-methyl-acridinium ion derivatives as efficient electron mediators and Ru-based catalysts
Yamada, Yusuke,Yano, Kentaro,Fukuzumi, Shunichi
, p. 1573 - 1581 (2012)
Photocatalytic hydrogen evolution has been performed by photoirradiation (λ>420nm) of a mixed solution of a phthalate buffer and acetonitrile (MeCN) (1:1 (v/v)) containing EDTA disodium salt (EDTA), [RuII(bpy) 3]2+ (bpy=2,
Organization of supra molecular assembly of 9-mesityl-10- carboxymethylacridinium ion and fullerene clusters on TiO2 nanoparticles for light energy conversion
Hasobe, Taku,Hattori, Shigeki,Kamat, Prashant V.,Wada, Yuji,Fukuzumi, Shunichi
, p. 372 - 380 (2005)
TiO2 nanoparticles modified with composite nanoclusters of 9-mesityl-10-carboxymethylacridinium ion (Mes-Acr+-COOH) and fullerene (C60) in acetonitrile-toluene (3:1, v/v) were deposited as thin films on nanostructured SnO
Access to Stable Quaternary Phosphiranium Salts by P-Alkylation and P-Arylation of Phosphiranes
Alayrac, Carole,Botella, Clément,Comesse, Sébastien,Dalla, Vincent,Gasnot, Julien,Gaumont, Annie-Claude,Lakhdar, Sami,Taillier, Catherine
supporting information, p. 883 - 888 (2020/05/28)
We report the preparation of phosphiranium salts by quaternarization of phosphiranes, a class of sensitive, highly strained, and poorly nucleophilic cyclic phosphines. High-yielding introduction of a varied set of alkyl groups including methylene ester ar
Mild copper-catalyzed fluorination of alkyl triflates with potassium fluoride
Dang, Hester,Mailig, Melrose,Lalic, Gojko
supporting information, p. 6473 - 6476 (2014/06/24)
A chemoselective catalytic fluorination of alkyl triflates is described using potassium fluoride as a fluoride source. Excellent yields of the desired alkyl fluorides are obtained after one hour at 45°C using 2 mol% of the copper catalyst. With 10 mol% of the catalyst, full conversion can be achieved in less than 10 minutes at 45°C, and thus makes this procedure potentially suited for the preparation of 18F-labeled PET probes. As a result of the mild reaction conditions, only the substitution products are observed with no evidence of common side reactions, such as elimination. Reported is a preliminary study of the reaction scope, which demonstrates that the fluorination can be performed in the presence of a wide range of functional groups. Evidence suggests an unusual role of the [IPrCuOTf] catalyst as a phase-transfer catalyst and points to [IPrCuF] as the active fluorinating reagent (IPr=1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene).
Assemblies of artificial photosynthetic reaction centres
Fukuzumi, Shunichi,Ohkubo, Kei
scheme or table, p. 4575 - 4587 (2012/06/18)
Nature harnesses solar energy for photosynthesis in which one reaction centre is associated with a number of light harvesting units. The reaction centre and light-harvesting units are assembled by non-covalent interactions such as hydrogen bonding and π-π interactions. This article presents various strategies to assemble artificial photosynthetic reaction centres composed of multiple light harvesting units and charge-separation units, which are connected by non-covalent bonding as well as covalent bonding. First light-harvesting units are assembled on alkanethiolate-monolayer-protected metal nanoparticles (MNPs), which are connected with electron acceptors by non-covalent bonding. Light-harvesting units can also be assembled using dendrimers and oligopeptides to combine with electron acceptors by π-π interactions. The cup-shaped nanocarbons generated by the electron-transfer reduction of cup-stacked carbon nanotubes have been functionalized with a number of porphyrins acting as light-harvesting units as well as electron donors. In each case, the photodynamics of assemblies of artificial photosynthetic reaction centres have revealed efficient energy transfer and electron transfer to afford long-lived charge-separated states.
Photoelectrochemical properties of supramolecular composite of fullerene nanoclusters and 9-mesityl-10-carboxymethylacridinium ion on SnO2
Hasobe, Taku,Hattori, Shigeki,Kotani, Hiroaki,Ohkubo, Kei,Hosomizu, Kohei,Imahori, Hiroshi,Kamat, Prashant V.,Fukuzumi, Shunichi
, p. 3103 - 3106 (2007/10/03)
(Chemical Equation Presented) The photovoltaic cell composed of both fullerene nanoclusters and 9-mesityl-10-carboxymethylacridinium ion exhibits significant enhancement in the photoelectrochemical performance as well as broader photoresponse in the visible and near-infrared regions as compared with the reference system containing only each component.
Synthesis of conformationally constrained DTPA analogues. Incorporation of the ethylenediamine units as aminopyrrolidines
Williams,Rapoport
, p. 3616 - 3625 (2007/10/02)
The synthesis of conformationally constrained diethylenetriaminepentaacetic acid (DTPA) analogues is an effort to probe the relationship between ligand structure and metal complex stability. In the pursuit of this objective, diastereomerically and enantiomerically pure mono- and bis-pyrrolidine analogues of DTPA have been prepared from trans-4-hydroxy-L-proline. The mono-pyrrolidine chelator 1 was constructed from a single hydroxyproline unit and an ethylenediamine moiety while two hydroxyproline-derived fragments 4e or 14b and 9b were coupled by N-alkylation of a triflate to afford the core bis-pyrrolidine structures: optically active 10 and meso-15. Deprotection of the triamine pentaesters 12 and 17 afforded the triamine pentaacetic acids 2 and 3 as their hydrochloride salts. The stereochemical homogeneity of precursor esters 12 and 17 was determined by HPLC using authentic epimeric standards to establish that essentially no racemization of the original amino acid α-center had occurred. Some loss of stereochemical homogeniety was encountered in the synthesis of 10 and 15 by N-alkylation of aminoproline 9b with a hydroxyproline-derived triflate, which had proceeded with some retention of configuration. The diastereomeric impurities were removed by crystallization of the respective benzyl carbamates. Bis-pyrrolidine pentaacids 2 and 3 formed isolable chelates with gadolinium and lutetium. A comparision of the lutetium chelates of 2 and 3 by NMR revealed significant differences which were reflective of a rigid structure with 2, while metal complexation with 3 was structurally less defined.
