Fluorescent Sugar and Uridine Conjugates of 1,8-Naphthalimides with Methyl and Ferrocenyl Headgroups

Abstract

The first amphiphilic sugar and deoxyuridine conjugates with a 4-ethynyl-1,8-N-methylnaphthalimide linker, a 4-ethynyldeoxyuridine conjugate with a N-undecylferrocenyl headgroup, and a 1,8-naphthalimide with a 2,3,4,6-tetra-O-acetate-β-d-glucopyranoside headgroup have been synthesized. A novel acrylate monomeric precursor for sugar–ethynylnaphthalimide polymers is also reported. The ethynyl tether forms complexes with Co2(CO)8 and Co2(CO)6dppm. The single-crystal X-ray structures of 2′-propynyl-2,3,4,6-tetra-O-acetate-β-d-glucopyranoside 4 and 4-(2′-propynyl-2,3,4,6-tetra-O-acetate-β-d-glucopyranoside)-N-methyl-1,8-naphthalimide 6 are also reported. With the exception of the Co2 complexes, the sugar and deoxyuridine conjugates are strongly fluorescent. ‘On–off’ fluorescent switching is achieved in the deoxyuridine conjugate with an undecylferrocenyl headgroup.