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Abstract Ionic liquids (ILs) have emerged as promising biomaterials for enhancing drug delivery by functionalizing polymeric nanoparticles (NPs). Despite the biocompatibility and biofunctionalization they confer upon the NPs, little is understood regarding the degree in which non‐covalent interactions, particularly hydrogen bonding and electrostatic interactions, govern IL‐NP supramolecular assembly. Herein, we use salt (0‐1 M sodium sulfate) and acid (0.25 M hydrochloric acid at pH 4.8) titrations to disrupt IL‐functionalized nanoassembly for four different polymeric platforms during synthesis. Through quantitative¹H‐nuclear magnetic resonance spectroscopy and dynamic light scattering, we demonstrate that the driving force of choline trans‐2‐hexenoate (CA2HA 1:1) IL assembly varies with either hydrogen bonding or electrostatics dominating, depending on the structure of the polymeric platform. In particular, the covalently bound or branched 50:50 block co‐polymer systems (diblock PEG‐PLGA [DPP] and polycaprolactone [PCl]‐poly[amidoamine] amine‐based linear‐dendritic block co‐polymer) are predominantly affected by hydrogen bonding disruption. In contrast, a purely linear block co‐polymer system (carboxylic acid terminated poly[lactic‐co‐glycolic acid]) necessitates both electrostatics and hydrogen bonding to assemble with IL and a two‐component electrostatically bound system (electrostatic PEG‐PLGA [EPP]) favors hydrogen‐bonding with electrostatics serving as a secondary role. 

Abstract This study introduces a benzodithiophene‐S,S‐tetraoxide (BDTT) monomer as an acceptor and 3,4‐ethylenedioxythiophene flanked thiophene (TEDOT₂) and terthiophene (T₃) as donor molecules for polymer formation. The synthesis of thepoly(TEDOT₂‐BDTT)andpoly(T₃‐BDTT)copolymers was performed via a single‐step monomer radical formation that is typically associated with electropolymerization methods. The electropolymerization is controlled by using a suitable monomer stoichiometric ratio that enables the deposition of copolymer thin films on the working electrode. Resultant copolymers were investigated by electrochemical analysis and their electronic properties are discussed in detail. A low average electron transport resistance of 16.5 Ω was found forpoly(TEDOT₂‐BDTT), indicating excellent conductive behavior. Solid‐state absorbance and emission studies of the copolymers show visible to near‐infrared spectral activity. Results support an effective strategy towards highly efficient electronically conducting polymers (ECPs) based on a unique BDTT monomer.