Synthesis and optoelectronic properties of novel organosoluble polynorbornenes containing asymmetric pyrenyl and electroactive substituents via ring‐opening metathesis polymerization

Abstract

Novel polynorbornenes, poly(NBPYTPA), and poly (HNBPYTPA), containing chromophoric and electroactive groups were synthesized by ring-opening metathesis polymerization using Grubbs' catalysts and followed hydrogenation, respectively. The glass transition temperatures (T g ) of poly(NBPYTPA) and hydrogenated poly(HNBPYTPA) were 195 and 165 C, respectively. The 10% weight-loss temperatures of hydrogenated poly (HNBPYTPA) and poly(NBPYTPA) were up to 465 and 420 C, respectively. The photoluminescence emission spectra of poly (HNBPYTPA) showed strong solvatochromic property, revealing that poly(HNBPYTPA) underwent remarkable bathochromic shifts with an increase in solvent polarity. The cyclic voltammogram of poly(HNBPYTPA) film cast onto an indium tin oxide (ITO)-coated glass substrate exhibited two reversible oxidation redox couples at 0.8 and 1.2 V versus Ag/Ag þ in acetonitrile solution. The electrochromic characteristics of poly(HNBPYTPA) showed reversibility, with color changes from yellow to blue and then to red upon the application of potentials from 0 to 1.3 V. V C 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49: 5350-5357, 2011

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

“…Liaw and co-workers synthesized polynorbornene-based polymer 275 ( Scheme 57 a), potentially applicable in optical communications and biomedicine, by Pd-catalyzed N-arylation. 198 The electroactive pyrenyl and TPA components of the polymer were connected by coupling aryl bromide 273 with N -alkylarylamine 274 (74%). 199 The reaction was enabled by an L3a -based catalyst in the presence of NaO- t -Bu.…”

“…As shown in this section, intermolecular C–N couplings of secondary anilines are robust processes for accessing relevant organic materials, including those with high molecular weights. Liaw and co-workers synthesized polynorbornene-based polymer 275 (Scheme a), potentially applicable in optical communications and biomedicine, by Pd-catalyzed N-arylation . The electroactive pyrenyl and TPA components of the polymer were connected by coupling aryl bromide 273 with N -alkylarylamine 274 (74%) .…”

Polynorbornene dicarboximide/amine functionalized graphene hybrids for potential oxygen barrier films

“…Polynorbornene dicarboximide (PND) with linear aliphatic and aromatic substituents has been synthesized via ring‐opening metathesis polymerization (ROMP) 18–23. The polynorbornene dicarboximide by ROMP of exo‐norbornene‐5,6‐dicarboximide uses well‐defined ruthenium alkylidene as a catalyst.…”

Recent advances in electrochromic polymers

“…The colour changed from colourless (0.0 V) to green (0.9 V) to light-blue (1.2 V) to darkblue (1.5 V). In the same year, a bi-triarylamine with the pyrene-TPA combination was attached as the pendant group [59] (see 17 in Fig. 16, Table 3).…”