Separation of π-Electron-Rich Compounds by Using Anion-Exchange Resin Modified with Cu2+-Phthalocyanine Derivative as Stationary Phase for Chromatography

Abstract

Recently, many HPLC stationary phases mainly based on π-π electron interaction (π-π interaction) have been developed for the separation of π-electron-rich compounds. Those include silica gels binding Cu 2+ -phthalocyanine 1-3 and In 3+ -porphine 4,5 and pyrene 6,7 derivatives. However, the preparation of such silica gels requires troublesome procedures 2,4,6 and the base silica gels for HPLC are relatively expensive. On the other hand, we have found that anionic metal-porphines are easily fastened on an ordinary anion-exchange resin through electrostatic and hydrophobic interactions. 8-13These facts led us to develop a stationary phase by modifying an anion-exchange resin with anionic Cu 2+ -phthalocyanine derivative (Cu-PCS r ), which would be prepared easily and cheaply. In the present paper, we would like to report briefly the utility of the resultant resin (hereinafter referred to as Cu-PCS r ) as a stationary phase for the separation of π-electron-rich compounds.

Synthesis and evaluation of a ferrocene-bonded silica phase for reversed-phase high-performance liquid chromatography

“…Cu 2+-and Ni2+-phthalocyanine [13] derivatives, metal porphyrins [14], and a variety of organometallic iron complexes [15] have recently been immobilized on silica gel and used to separate polycyclic aromatic hydrocarbons (PAH) under normal-phase conditions.…”

π-π Electron Interaction Property of HPLC Anion-Exchange Resin Modified with Cu2+-Phthalocyanine Derivative

“…6 The resultant Cu-PCSMCI (12.5, 25 or 50 µmol Cu-PCS/g dry MCI) was filtered, washed with water and then acetone, and dried under a vacuum to obtain Cu-PCSMCI. All of the modified resins were stable to temperature, moisture and storage, and Cu-PCS on the MCI was not eluted with water and methanol at all.…”

Development of N-ferrocenyl(benzoyl)amino-acid esters stationary phase for high performance liquid chromatography

“…The grafting on silica gel of electron acceptor molecules bearing transition metal metallocenes [1][2][3][4][5] is another investigated field of research [6][7]. In recent years, the ferrocene-bonded stationary phase has attracted considerable attention in liquid chromatography due to its varieties of separation mechanisms, including hydrophobic, hydrogen bonding, π-π, dipole-dipole and charge-transfer interactions [8][9][10][11][12].…”