Precisely designed perylene bisimide-substituted polyethylene with a high glass transition temperature and an ordered architecture

Abstract

A polyethylene with a precise repeat of perylene bisimide branches was synthesized by acyclic diene metathesis polymerization and hydrogenation of the as-synthesized polymer, and displayed good thermal stability and an ordered architecture.

Scalable Route to Electroactive and Light Active Perylene Diimide Dye Polymer Binder for Lithium-Ion Batteries

“…In the solid state, however, polymer 6 is nonfluorescent. X-ray diffractions ( Figure 2 b), obtained with a Cu Kα source, however, display a broad diffraction pattern, around 20–25°, indicating stacking of the aromatic planes with a large 4–4.5 Å spacing, similar to the observations reported by Song et al 18 Since we observed this difference in stacking of our polymer before and after casting ( Figure 2 c,d), we carried out small-angle X-ray scattering/wide-angle X-ray scattering (SAXS/WAXS) measurements to elucidate the possible morphological changes. For this purpose, analyses using synchrotron X-rays were performed on the PPDI powders before casting (i.e., unprocessed PPDI) and after solubilization of the polymer and evaporation of the solvent (i.e., processed PPDI).…”

“… 16 , 17 However, monohydroxy tetrachloro-PDIs (such as compound 4 in Scheme 1 b) have been previously synthesized by a one-step reaction in which two different amines react simultaneously with 1,6,7,12-tetrachloroperylene dianhydride (tetrachloro-PDA). 18 This method yields a statistical mixture of two symmetric and one nonsymmetric PDIs. This approach may be acceptable for a quick and small-scale exploratory synthesis using low-cost starting materials.…”

Synthesis and characterization of functional polyethylene with regularly distributed thioester pendants via ring‐opening metathesis polymerization

“…Ring‐Opening Metathesis Polymerization (ROMP) of strained monocyclic or dicyclic olefins such as cyclopentene, cyclooctene, and norbornene, using ruthenium‐based catalysts provides an alternative strategy to functional polyethylene. ROMP represents an equally powerful method to prepare perfectly linear polyethylene and its copolymers as compared to acyclic diene metathesis (ADMET) polymerization and other newly developed sequence control methods . Notably, ruthenium‐based catalysts have been preferentially chosen to catalyze the polymerization for their remarkable catalysis efficiency, thermal and chemical stability, and excellent tolerance toward a variety of polar groups such as ester, hydroxyl, and thioether .…”

“…ROMP represents an equally powerful method to prepare perfectly linear polyethylene and its copolymers as compared to acyclic diene metathesis (ADMET) polymerization and other newly developed sequence control methods. [28][29][30][31][32][33][34] Notably, ruthenium-based catalysts have been preferentially chosen to catalyze the polymerization for their remarkable catalysis efficiency, thermal and chemical stability, 35,36 and excellent tolerance toward a variety of polar groups such as ester, hydroxyl, and thioether. 7,[37][38][39][40] It has been difficult to effectively prepare polymers with short spacer between the pendent functional group and the backbone by ADMET, as cyclization cannot be ignored when the spacer is shorter than 7 methylenes.…”

Tuning layered superstructures in precision polymers

“…According to a recent study, precision polyethylenes containing regularly spaced acidic groups can be used for efficient ion transport 5 . Similarly, well-ordered arrangement of ring-like pendant groups such as perylene bisimide or terfluorene groups could be used to design advanced organic opto-electronic devices 15,16 .…”