Open AccessBiofunctionalization of Water-Soluble poly(Phenylene Ethynylene)s
Author(s) -
Han Sun,
Daniel Martínez,
Zhiliang Li,
Kirk S. Schanze
Publication year - 2020
Publication title -
acs applied materials and interfaces
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.535
H-Index - 228
eISSN - 1944-8252
pISSN - 1944-8244
DOI - 10.1021/acsami.0c15464
Subject(s) - covalent bond , conjugated system , polymer , polymer chemistry , materials science , rhodamine b , rhodamine , amide , sulfonate , ionic bonding , amine gas treating , combinatorial chemistry , chemistry , organic chemistry , fluorescence , ion , physics , sodium , photocatalysis , quantum mechanics , catalysis
We report the use of amide coupling chemistry to covalently link five different biofunctional groups onto an anionic water-soluble poly(phenylene ethynylene) (PPE) polymer. Two of the biofunctionalized PPEs are used in prototype applications, including pH sensing and flow cytometry labeling. The PPE is functionalized with carboxylate (R-CO 2 - ) and sulfonate (R-SO 3 - ) ionic groups. By using an activated ester, the amine-functionalized groups are covalently linked to the PPE polymer via amide linkages. The reaction chemistry is optimized using biotin-ethylene diamine, making it possible to control the loading of the biotin functionality on the PPE chains. Using the optimized approach, a family of five PPEs were prepared that contain biotin, rhodamine, cholesterol, mannose, or folic acid moieties appended to the polymer backbones. The rhodamine- and biotin-modified PPEs were further applied for pH response and flow cytometry applications. The reported approach can be utilized for other classes of water-soluble conjugated polymers, allowing facile development of a variety of new functionalized water-soluble conjugated polymers for a range of applications including sensing, bioimaging, and flow cytometry analysis.