122590-78-7Relevant articles and documents
Chemistry of bifunctional photoprobes. 1. Perfluoroaryl azido functionalized phosphorus hydrazides as novel photoreactive heterobifunctional chelating agents: High efficiency nitrene insertion on model solvents and proteins
Pandurangi,Karra,Katti,Kuntz,Volkert
, p. 2798 - 2807 (1997)
Synthesis and evaluation of a new class of photochemically activated heterobifunctional chelating agents for protein modification is described. Selective functionalization of perfluoroaryl azides by versatile phosphorus hydrazide ligating systems 2 and 3 for the complexation of transition metals and analogous radiometals form the basis for these new agents. The utility of the photogenerated precursors from these bifunctional agents to form covalent attachments is demonstrated through examination of C-H bond insertion on cyclohexane. Representative amide-coupled phosphorus hydrazides 5 and 6 provide > 78% insertion of the probe into unactivated C-H bonds of cyclohexane with short photolysis times. Photoconjugation of the photoactivable heterobifunctional chelating agent 6 and its Pd metalated analog 7 with HSA is also evaluated. The uncomplexed chelate appears to add to HSA with high efficiency, consistent with the observed 82% bond insertion into model solvents. Covalent attachment of 7, evaluated through the use of 109Pd, was estimated to be between 49% and 74% with the uncertainty arising because of prephotolysis association of the 109Pd complex with HSA. The application of in situ 19F NMR to distinguish between bond insertion and noninsertion processes is demonstrated. These results suggest that functionalized perfluoroaryl azido phosphorus hydrazides may find utility as heterobifunctional photolabeling agents for attaching radionuclides to proteins and antibodies.
Acid-responsive organogel mediated by arene-perfluoroarene and hydrogen bonding interactions
Wu, Huixian,Ni, Ben-Bo,Wang, Chong,Zhai, Feng,Ma, Yuguo
experimental part, p. 5486 - 5492 (2012/08/14)
A phenyl and a 2,3,5,6-tetrafluorophenyl ring, each bearing a tris(n-dodecyloxy)benzylamine moiety via an amide bond, were tethered together through an imine linkage to give a non-covalent synthon (imine 1) with a strong capacity of supramolecular self-as
Smartly designed photoreactive silica nanoparticles and their reactivity
Peled, Anna,Naddaka, Maria,Lellouche, Jean-Paul
supporting information; experimental part, p. 11511 - 11517 (2011/10/18)
Monodisperse, colloidal silica nanoparticles (NPs) are being widely investigated due to a variety of applications in various fields of chemistry. Many works utilize incorporation of various functional groups to silica NPs for their further modifications. However, at present no benzophenone (BPh) or phenyl azide (PA) containing silica NPs exist. Upon UV irradiation BPh and PA form highly reactive species that react with any organic material. Here we present a convenient method for the preparation of novel hybrid photoreactive silica NPs (denoted as SiO2@photoreactive group) prepared by co-condensation of photoreactive organosilanes and tetraethyl orthosilicate (TEOS) to obtain SiO2@PA and SiO2@BPh NPs. The reactivity of these two types of silica NPs is compared to that of perfluorinated phenyl azide (PFPA) based SiO2 NPs. The reactivity evaluation is carried out by the reaction of the three types of SiO2 NPs with highly inert poly(2-chloro-paraxylelene) films. It is found that, in contrast to what is stated in the literature, PA is much more reactive than PFPA, when dealing with solid state photochemical reactions. Next, photoreactive silica NPs on polymer films are used as an intermediate functional phase for a second modification step using silane-based chemistry. A successful incorporation of amine functionality onto silica NPs is achieved by their reaction with 3-aminopropyltriethoxysilane (APTES) and is verified by fluorescence microscopy. This strategy provides a general and versatile route to efficient functionalization of silica by light.
