Efficient synthesis of fluorescent squaraine rotaxane dendrimers.
A squaraine rotaxane scaffold with four alkyne groups is readily converted into a range of dendritic architectures using high-yielding copper-catalyzed alkyne azide cycloaddition (CuAAC) chemistry. A convergent synthesis approach is more efficient than a divergent pathway. Dendritic squaraine rotaxanes with peripheral amine groups can be further functionalized to produce multivalent deep-red fluorescent derivatives that exhibit high brightness and outstanding chemical stability in biological solution. The surface groups on these functionalized fluorescent dendrimers include guanidinium, mannose, and phosphatidylcholine.
Xiao
Shuzhang
S
Department of Chemistry and Biochemistry, and Walther Cancer Research Center, 251 Nieuwland Science Hall, University of Notre Dame, Indiana 46556, USA.
Fu
Na
N
Peckham
Kaitlin
K
Smith
Bradley D
BD
D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003503:Cyclobutanes / Q000138:chemical synthesis* / Q000737:chemistry; D050091:Dendrimers / Q000138:chemical synthesis* / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry; D043862:Rotaxanes / Q000138:chemical synthesis* / Q000737:chemistry
D003503:Cyclobutanes; D050091:Dendrimers; D005456:Fluorescent Dyes; D010636:Phenols; D043862:Rotaxanes; C480596:squaraine; D003300:Copper