Fluorophilic Sigma(σ)-Lock Self-Healable Copolymers

Angew Chem Int Ed Engl. 2024 May 13:e202405504. doi: 10.1002/anie.202405504. Online ahead of print.

Abstract

Although F-containing molecules and macromolecules are often used in molecular biology to increase the binding with Lewis acidic groups by introducing favorable C-F dipoles, there is virtually no experimental evidence and limited understanding of the nature of these interactions, especially their role in synthetic polymeric materials. These studies elucidate the molecular origin of inter- and intra-chain interactions responsible for self-healing of F-containing copolymers composed of pentafluorostyrene and n-butyl acrylate units (p(PFS/nBA). Guided by dynamic surface oscillating force (SOF) and spectroscopic measurements supported by molecular dynamics (MD) simulations, these studies show that the reformation of σ-σ orbitals in -C-F of PFS and CH3CH2- of nBA units enables the recovery of entropic energy via flouorophilic-σ-lock van der Waals forces when PFS/nBA molar ratios are ~50/50. The strength of these interactions determined experimentally for self-healable PFS/nBA compositions is in the order ~0.3 kcal/mol which primarily comes from flouorophilic-σ-lock (~70%) contributions. These interactions are significantly diminished for non-self-healable counterparts. Strongly polarized -C-F σ orbitals create lateral dipolar forces enhancing the affinity towards -C-H orbitals, facilitating energetically favorable interactions. Entropic recovery driven by non-covalent bonding offers a valuable tool in designing materials with unique functionalities, particularly self-healable batteries or other energy storage devices.

Keywords: Flouorophilic-σ-lock interactions; Fluorine-containing copolymers; Self-healing.