Journal
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
Volume 24, Issue 2, Pages -Publisher
MDPI
DOI: 10.3390/ijms24021662
Keywords
polyurethane dendrimers; homodendrimers; heterodendrimers; Janus dendrimers; fluorescence; click reaction; late-stage modification; absorption; emission
Ask authors/readers for more resources
In this study, fluorescent polyurethane homodendrimers and Janus dendrimers were synthesized overcoming the challenges posed by the reactivity of isocyanates. By using a one-pot multicomponent Curtius reaction, polyurethane dendrons (G1-G3) were successfully synthesized. The alkyne periphery of the dendrons was modified using a copper catalyzed azide-alkyne click reaction (CuAAC) to form fluorescent dendrons. The mixture of two different functionalized dendrons with a difunctional core resulted in the formation of three dendrimers, including two homodendrimers and a Janus dendrimer, with the Janus dendrimer being the predominant product.
Fluorescent dendrimers have wide applications in biomedical and materials science. Here, we report the synthesis of fluorescent polyurethane homodendrimers and Janus dendrimers, which often pose challenges due to the inherent reactivity of isocyanates. Polyurethane dendrons (G1-G3) were synthesized via a convergent method using a one-pot multicomponent Curtius reaction as a crucial step to establish urethane linkages. The alkyne periphery of the G1-G3 dendrons was modified by a copper catalyzed azide-alkyne click reaction (CuAAC) to form fluorescent dendrons. In the reaction of the surfaces functionalized two different dendrons with a difunctional core, a mixture of three dendrimers consisting of two homodendrimers and a Janus dendrimer were obtained. The Janus dendrimer accounted for a higher proportion in the products' distribution, being as high as 93% for G3. The photophysical properties of Janus dendrimers showed the fluorescence resonance energy transfer (FRET) from one to the other fluorophore of the dendrimer. The FRET observation accompanied by a large Stokes shift make these dendrimers potential candidates for the detection and tracking of interactions between the biomolecules, as well as potential candidates for fluorescence imaging.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available