Mussel-Inspired One-Pot Synthesis of a Fluorescent and Water-Soluble Polydopamine-Polyethyleneimine Copolymer

Abstract

Inspired by the molecular mechanics of mussel adhesive formation, a novel water-soluble fluorescent macromolecule (polydopamine-polyethyleneimine (PDA-PEI)) is prepared by one-pot copolymerization of dopamine (DA) and PEI. In this method, DA is polymerized to form PDA, which is then coupled with PEI mainly through Michael addition. The fluorescence property of PDA-PEI is mainly attributed to the Michael addition of PEI on the 5,6-dihydroxyindole (DHI) units of PDA, where PEI can form hydrogen bonds with oxidative products such as DHI and force the DHI units to twist out of plane, resulting in a decrease in the intra- and intermolecular coupling of PDA. In addition, the influence of various metal cations on the fluorescence of the PDA-PEI copolymer is investigated. This work may facilitate the development of new strategies for controlling the emission characteristics of PDA.

Insight into membrane selectivity of linear and branched polyethylenimines and their potential as biocides for advanced wound dressings

“…When compared to pristine gelatin mats, substantial changes were observed in the mats containing LPEI/BPEI after polydopamine crosslinking. The appearance of a broad hump around 2110 cm À1 , assigned to the substituted imines (m substitutedC @ N ) confirmed the crosslinking of LPEI to dopamine and gelatin [65][66][67]. The presence of an intense peak at 3494 cm À1 (assigned to the m (O-H/N-H) of polydopamine) and a shoulder around 3278 cm À1 (assigned to the 2°amine groups of LPEI/BPEI) further indicated the presence of LPEI/BPEI within polydopamine crosslinked gelatin mats.…”

Highly regenerable alkali-resistant magnetic nanoparticles inspired by mussels for rapid selective dye removal offer high-efficiency environmental remediation

“…42 Thus the ultrathin layer on Fe 3 O 4 @PDA/PEI should be due to the decrease of intra-and intermolecular noncovalent interactions caused by the addition of PEI. 42 Thus the ultrathin layer on Fe 3 O 4 @PDA/PEI should be due to the decrease of intra-and intermolecular noncovalent interactions caused by the addition of PEI.…”

Chemistry of polydopamine analogues

“…The films exhibited enhanced solvent processability, thermal stability and a low adsorption of proteins and thus were claimed promising for antifouling coatings. When DA was mixed with PEI and oxidatively polymerized in air and Tris buffer, covalent linkage between the amino groups of PEI and PDA could be assumed by Schiff base formation or Michael type addition (Scheme , bottom; Scheme ) . This methodology was used to obtain free standing films wherein the inherent rigidity of PDA is suspended and in the fabrication of organic – inorganic hybrid microcapsules useful for immobilization of enzymes, dye absorption and glucose sensing .…”

“…This methodology was used to obtain free standing films wherein the inherent rigidity of PDA is suspended and in the fabrication of organic – inorganic hybrid microcapsules useful for immobilization of enzymes, dye absorption and glucose sensing . Furthermore, the PEI – PDA composites exhibit fluorescence that is specifically affected by metal ions …”

“…Oxidative polymerization of DA in the presence of other polymers without covalent linkage (top) and with covalent linkage (middle, bottom) …”