Macromolecules, Vol.50, No.18, 7091-7101, 2017
Water-Soluble Fluorescent Nanoparticles from Supramolecular Amphiphiles Featuring Heterocomplementary Multiple Hydrogen Bonding
We describe a facile strategy, involving bioinspired noncovalent molecular recognition, for fabricating water-dispersible luminescent polymer dots without any ionic groups. We first synthesized the thymine-functionalized conjugated polymers PC-T and PTC-T through conventional Suzuki coupling polymerization and copper(I)-catalyzed alkyne/azide cycloaddition (CuAAC). These multiple-hydrogen-bonding materials exhibited distinct luminescent properties in protic and aprotic solvents as well as attractive thermal properties and stabilities; most importantly, they had the ability to pair with complementary base units. Next, we prepared the hydrophilic polymer PEG-A and examined its molecular recognition with PC-T and PTC-T through DNA-like adenine thymine (AT) base pairing. We used transmission electron microscopy (TEM) and dynamic light scattering (DLS) to determine the size distributions and dispersibilities of the resulting supramolecular micelles, which appeared as polymeric dots with high signal-to-background ratios through fluorescence microscopy. The PEG shells of these micelles functioned as biomimetic surfaces that sustained the biocompatibility for practical usage. Our results suggest that supramolecular self-assembly through specific nucleobase recognition appears to be a reliable process with which to apply conjugated polymers into, for example, modern biological analysis.