Dual Bodipy fluorophores linked by polyethyleneglycol spacers

作者：Mula Soumyaditya; Ulrich Gilles; Ziessel Raymond^*

来源：Tetrahedron Letters, 2009, 50(46): 6383-6388.

DOI：10.1016/j.tetlet.2009.08.091

• Bodipys'
• Dual dyes
• Amino groups
• Polyethyleneglycol
• Fluorescence
• Sensors

Several Bodipy dyes were synthesized with various substituents designed to potentially interact with adventurous cations including protons. Among the different synthetic strategies, protection of the amino group by a BOC appears efficient for the substitution of the fluoro groups on the boron by Grignard reagents. Single alkylation on the amino-Bodipy compounds by a polyethyleneglycol chain bearing an alkyne end group is feasible using a biphasic strategy. Linkage of a blue dye on the alkyne fragment is promoted by palladium(0) and it provides novel dual donor-acceptor dyes. Fluorescence of the mono-alkylated amino dyes is heavily quenched but restored by protonation or interaction with Fe(II) salts. Very efficient energy transfer from the donor (energy input at 20,000 cm(-1)) to the acceptor (energy output at 15,100 cm(-1)) is quantitative and not distance dependent.

• 出版日期2009-11-18