A Ligand System for the Flexible Functionalization of Quantum Dots via Click Chemistry

We present a novel ligand, 5‐norbornene‐2‐nonanoic acid, which can be directly added during established quantum dot (QD) syntheses in organic solvents to generate “clickable” QDs at a few hundred nmol scale. This ligand has a carboxyl group at one terminus to bind to the surface of QDs and a norborn...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2018-04, Vol.57 (17), p.4652-4656
Main Authors: Chen, Yue, Cordero, Jose M., Wang, Hua, Franke, Daniel, Achorn, Odin B., Freyria, Francesca S., Coropceanu, Igor, Wei, He, Chen, Ou, Mooney, David J., Bawendi, Moungi G.
Format: Article
Language:English
Subjects:
Cancer
capping ligand
Carboxyl group
cell labeling
Chemical synthesis
click chemistry
Ligands
Organic solvents
Quantum dots
Sugar
surface modification
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Summary:We present a novel ligand, 5‐norbornene‐2‐nonanoic acid, which can be directly added during established quantum dot (QD) syntheses in organic solvents to generate “clickable” QDs at a few hundred nmol scale. This ligand has a carboxyl group at one terminus to bind to the surface of QDs and a norbornene group at the opposite end that enables straightforward phase transfer of QDs into aqueous solutions via efficient norbornene/tetrazine click chemistry. Our ligand system removes the traditional ligand‐exchange step and can produce water‐soluble QDs with a high quantum yield and a small hydrodynamic diameter of approximately 12 nm at an order of magnitude higher scale than previous methods. We demonstrate the effectiveness of our approach by incubating azido‐functionalized CdSe/CdS QDs with 4T1 cancer cells that are metabolically labeled with a dibenzocyclooctyne‐bearing unnatural sugar. The QDs exhibit high targeting efficiency and minimal nonspecific binding. Join the dots: A norbornene‐bearing carboxylic acid ligand can be added to quantum dot (QD) syntheses and generate “clickable” QDs. Further click reaction with a hydrophilic molecule yields water‐soluble QDs that are suitable for cell‐labeling applications.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201801113