The N⋯I Intermolecular Interaction as a General Protocol for the Formation of Perfluorocarbon–Hydrocarbon Supramolecular Architectures 1

Supramolecular Route to Fluorinated Coatings: Self-Assembly Between Poly(4-vinylpyridines) and Haloperfluorocarbons

“…[15,16] Amine and pyridyl nitrogens atoms, [17] as well as other neutral and anionic heteroatoms, [18±20] work as effective electron donors towards the electron-poor halogen atoms of halo-PFCs. Thanks to its high strength, specificity, and directionality, halogen bonding is well tailored to overcome the very low affinity existing between PFCs and hydrocarbons (HCs) and to assemble them into crystalline materials, stable in air at room temperature.…”

Perfluorocarbon-hydrocarbons self-assembly: halogen bonding mediated intermolecular recognition

“…For instance, when equimolar quantities of 1,2-diiodotetrafluoroethane 1a and N,N,N 0 ,N 0 -tetramethylethylenediamine (TMEDA, 2) are dissolved in chloroform, solvent evaporation under diffusion conditions affords the hybrid PFC-HC system 3 as white crystals stable in air at room temperature (Scheme 1) [24,25]. The system is composed by 1D infinite chains where the two modules alternate.…”

“…For instance, (E)-1,2-diiododifluoroethylene [33], perfluoro-1,4-diiodobutane, -1,6-diiodohexane, -1,8-diiodooctane (1b, 1c, and 1d, respectively) [24,25,[34][35][36], 1,2-and 1,4-diiodotetrafluorobenzene [37][38][39][40][41][42][43][44][45] as well as 1,2-, 1,3-, and 1,4-dibromotetrafluorobenzene [46] are acid modules that nicely follow this behaviour. The same holds for other compounds where a hydrocarbon spacer separates two 4-iodotetrafluorophenyl moieties [47].…”

Combining halogen bonds and hydrogen bonds in the modular assembly of heteromeric infinite 1-D chains

“…Similarly, various examples are reported 13 where tetrafluorodiiodobenzene, in combination with suitable dipyridyl derivatives, form infinite chains through I … Nheterocycle halogen bonds (Scheme 2, bottom). Similarly, various examples are reported 13 where tetrafluorodiiodobenzene, in combination with suitable dipyridyl derivatives, form infinite chains through I … Nheterocycle halogen bonds (Scheme 2, bottom).…”