Acridine-containing polymers

The synthetic route to acridine-containing polymers is outlined in Scheme I. 9-Methyl acridine (II) was prepared via 9-ethyl-malonate acridine by the method of Campbell et al (14), from 9-chloroacridine (I, Kodak), (mp. 117-8°C from ligroin). 9-(3hydro-xyethyl) acridine (III) was synthesized via the condensation of formaldehyde with II (15) (mp. 154-6°C, from ethanol-water). Metha-cryloylchloride, freshly distilled, was reacted with III in dry THF with pyridine as base to give IV, 2-(9-acridyl) ethylmethacrylate, purified by chromatography with silica gel/toluene to give red gum (IR 5.85 ym ester carbonyl stretch). 

Polymers containing chromophores such as acridine and azobenzene have also been prepared by palladium-catalyzed amination according to two approaches [222-224]. The first approach involved the polymerization of monomers containing the chromophore. For example, 4-aminoazobenzene was condensed with 1,3-dibromobenzene (Eq. (39)) or 4,4 -dibromobiphenyl ether to form polymeric materials with Mw values of 9.0 x 103 and 19 x 103, respectively. Alternatively, polymers prepared by polymerization of 4-bromostyrene or copolymerization of styrene and 4-bromostyrene were coupled with N-phenyl-4-amino azobenzene. Substitution of the aryl bromides by the amino azobenzene unit was essentially quantitative when using P(tBu)3 as the ligand. 

The photoinduced electron transfer to an ITO electrode was measured by an electrochemical method. The binary component monolayers complexed with anionic polymers were deposited on ITO electrodes, and the electrode was soaked in an aqueous 0.1 M KCl solution containing EDTA as a sacrificial electron donor. As shown in Fig. 7, the polyion complex monolayer deposited on the ITO electrode generated photocurrent with visible light irradiation (>450 nm). Anodic photosensitized current of the amphiphilic acridine dye 5 is enhanced by complex... 

The cell distribution of 3-amino-4-hydroxymethyl acridine derivatives 70 (Scheme 25), which has the N3—C4—16 substitution pattern, was studied by real-time fluorescence microscopy and SIMS structured illumination microscopy). The latter method required the introduction of an iodine atom at position 6 of the acridine which influences the Upophihcity but does not modify significantly the biological properties such as IC50 and subcellular localization (2009EJMC4758). A co-polymer 71 consisting of water-soluble maleic anhydride-containing poly[maleic anhydride-u/i-acrylic acid] (poly(MA-alt-AA) or MAAA) copolymer was modified with acriflavine (AF) which displayed antibacterial activity on EHEC and Staphylococcus aureus (2014MI2903). 

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