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A Ligand System for the Flexible Functionalization of Quantum Dots via Click Chemistry
Author(s) -
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.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201801113
Subject(s) - tetrazine , click chemistry , ligand (biochemistry) , quantum dot , chemistry , norbornene , surface modification , aqueous solution , quantum yield , combinatorial chemistry , nanotechnology , materials science , organic chemistry , polymer , polymerization , fluorescence , receptor , physics , biochemistry , quantum mechanics
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.