260396-55-2Relevant academic research and scientific papers
An efficient one-pot synthesis of new polyfunctional phosphorus acid amphiphiles
Vercruysse, Karine,Dejugnat, Christophe,Munoz, Aurelio,Etemad-Moghadam, Guita
, p. 281 - 289 (2000)
The addition reaction between the P-H bond of tetraoxyspirophosphoranes 1-2 and long-chain imines 3a-h (decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, and oleyl imines) occurs instantaneously at room temperature. It is diastereoselective, and quantitatively leads to the corresponding (α- aminoalkyl)spirophosphoranes 4a-h and 5e. The influence of the pentacoordinated phosphorus atom on the stereoselectivity of the Pudovik reaction might be attributed to the involvement of the rigid spirophosphoranide (P(v)) intermediate in the addition reaction. Selective and one- pot hydrolysis of these P-C bond spirophosphoranes readily proceeds either at room temperature in the presence of moist solvents to give the corresponding carboxyalkyl (α-aminoalkyl)phosphonic acid monoesters 6a-h and 7e, or the reaction may be carried out in the presence of 20% aqueous hydrochloric acid under reflux, to afford the free (α-aminoalkyl)phosphonic acid amphiphiles 8a-h in high yields. In contrast to their sodium salts, these single- and double-chained free and monoester phosphonic acid amphiphiles exist as zwitterions and are not soluble in water.
Imine-linked chemosensors for the detection of Zn2+ in biological samples
Saluja, Preeti,Bhardwaj, Vimal K.,Pandiyan, Thangarasu,Kaur, Simanpreet,Kaur, Navneet,Singh, Narinder
, p. 9784 - 9790 (2014/03/21)
A chemosensor 1 with a long hydrocarbon chain and polar end group is synthesized by the simple condensation reaction of a long chain amine with salicylaldehyde. A long chain hydrocarbon with a polar end group is used because of its solubility in an aqueous surfactant solution, which ensures that it can be used in a neutral water medium. The rationale for choosing an aryl aldehyde with -OH functionality is based upon the fact that a chelate ring consisting of an -OH group and an sp2 nitrogen donor is always better for the selective recognition of Zn2+. The sensor shows selective binding to Zn2+ in 1% Triton-X-100 solution. Binding of Zn2+ by sensor 3 leads to an approximately 300% enhancement in the fluorescence intensity of the sensor, due to the combined effects of excited state intramolecular proton transfer (ESIPT) and the inhibition of the photo-induced electron transfer (PET) process by the -OH group. The fluorescence emission profiles of sensor 1 show some changes in the low and high pH ranges, however the sensor remains stable in the pH range 4-9, which makes it appropriate for use in biological fluids.
