| Abstrakt: |
A series of H[sub 2]O and/or EtOH soluble, self-assembling quaternary ammonium salts containing a dansyl (DNS) fluorescent moiety suitable for attachment to both porous ([DNS-NH-(CH[sub 2])[sub 3]-NMe[sub 2]-R[sup +]][X[sup -]] (2; R = -Si(OMe)[sub 3], X[sup -] = Cl[sup -]) and non-porous (3a; R = -PO(OEt)[sub 2], 3b; -PO(Oi-Pr)[sub 2], 3c; -(PO(OH)[sub 2], X[sup -] = Br[sup -]), 4; ([DNS-NH-(CH[sub 2])[sub 3]-NMe[sub 2]-(CH[sub 2])[sub 3]-NH(CH[sub 2]PO(OEt)[sub 2])[sub 2][sup +]][Br], 5; R = -((CH[sub 2])[sub 3]SCOCH[sub 3], X[sup -] = CD, 6a; (R = -(CH[sub 2])nO(C[sub 6]H[sub 4])CO(C[sub 6]H[sub 5]), n = 3, X[sup -] = Br, 6b; n = 3, X[sup -] = Cr, 6c; n = 3, X[sup -] = I[sup -], 6d; n = 4, X[sup -] = Br[sup -], 6e; n = 4, X[sup -] = r, 6f; n = 6, X[sup -] = Br[sup -], 6g; n = 6, X[sup -] = Cl[sup -], 6h; n = 6, X[sup -] = D, 7; (R = -CH[sub 2]CH]CH[sub 2], X[sup -] = Br) surfaces were prepared from the precursor dansyl amine (1; DNS-NH-(CH[sub 2])[sub 3]- NMe[sub 2]). Compounds 1-7 were characterized by NMR (¹H, [sup 13]C, [sup 29]Si (2), [sup 31]P (3a-c, 4)) spectroscopy, HRMS, UV-Vis and fluorescence spectroscopy. Additional characterization of compounds 1 and 7 were carried out by X-ray structure determinations. Physical attachment of compound 2 to cotton surfaces after immersion in solutions containing fluorescent dyes was verified by exposure to UV light and by complexation with bromo-phenol blue that rendered the surfaces visibly blue in colour. Phosphorus containing dansyl fluorescent dye, 3c, was attached to a stainless steel surface by exposure to an aqueous solution containing this dye, resulting in the formation of a self-assembled fluorescent monolayer. UV cure of plastic surfaces (polypropylene, silicon medical tubing) coated with compound 6a resulted in the covalent attachment of the dyes. [ABSTRACT FROM AUTHOR] |
