Issue 11, 2014

Synthesis, structures and properties of self-assembling quaternary ammonium dansyl fluorescent tags for porous and non-porous surfaces

Abstract

A series of H2O and/or EtOH soluble, self-assembling quaternary ammonium salts containing a dansyl (DNS) fluorescent moiety suitable for attachment to both porous ([DNS–NH–(CH2)3–NMe2–R+][X] (2; R = –Si(OMe)3, X = Cl) and non-porous (3a; R = –PO(OEt)2, 3b; –PO(Oi-Pr)2, 3c; –(PO(OH)2, X = Br), 4; ([DNS–NH–(CH2)3–NMe2–(CH2)3–NH(CH2PO(OEt)2)2+][Br], 5; R = –((CH2)3SCOCH3, X = Cl), 6a; (R = –(CH2)nO(C6H4)CO(C6H5), n = 3, X = Br, 6b; n = 3, X = Cl, 6c; n = 3, X = I, 6d; n = 4, X = Br, 6e; n = 4, X = I, 6f; n = 6, X = Br, 6g; n = 6, X = Cl, 6h; n = 6, X = I), 7; (R = –CH2–CH[double bond, length as m-dash]CH2, X = Br) surfaces were prepared from the precursor dansyl amine (1; DNS–NH–(CH2)3–NMe2). Compounds 1–7 were characterized by NMR (1H, 13C, 29Si (2), 31P (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.

Graphical abstract: Synthesis, structures and properties of self-assembling quaternary ammonium dansyl fluorescent tags for porous and non-porous surfaces

Supplementary files

Article information

Article type
Paper
Submitted
19 พ.ย. 2556
Accepted
24 ม.ค. 2557
First published
28 ม.ค. 2557

J. Mater. Chem. B, 2014,2, 1509-1520

Author version available

Synthesis, structures and properties of self-assembling quaternary ammonium dansyl fluorescent tags for porous and non-porous surfaces

L. M. Porosa, K. B. Mistry, A. Mocella, H. Deng, S. Hamzehi, A. Caschera, A. J. Lough, G. Wolfaardt and D. A. Foucher, J. Mater. Chem. B, 2014, 2, 1509 DOI: 10.1039/C3TB21633K

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