Design and Synthesis of New Polymeric Materials for Organic Nonvolatile Electrical Bistable Storage Devices:  Poly(biphenylmethylene)s

Abstract

The synthesis of new polymers, poly(biphenylmethylene)s, derived from bistriflates of bisphenol-type monomers, by Ni(0)-mediated polymerization has been presented. These polymers are interesting because of the nature of the polymer backbone that contains biphenyl units separated by substituted methylene units. The solubility, mechanical properties, and electrical properties of the polymers can be altered by proper selection of the methylene substituents. Polymers and oligomers had molecular weights ranging from 2000 to 15 000 g/mol, as measured by calibrated gel permeation chromatography (GPC), though light scattering and MALDI studies indicate that GPC tends to underestimate the molecular weights of these polymers. The polymers have T g's between 230 and 300 °C and have thermal stabilities ranging from 400 to 493 °C. Thermally cross-linkable, 4-phenylethenyl end-capped oligomers were synthesized and fabricated into thin-film electronic devices, and preliminary results on their characterization are discussed. The unique structure of the polymer backbone makes these materials potentially interesting in electrical applications where large-band-gap polymers with good electron/hole mobility and good thermal and oxidative stability are required.

Nonvolatile Memory Elements Based on Organic Materials

“…Nominally homogeneous polymers have been used in MIM devices, including true insulators such as polystyrene [36,37] and acrylates [36] as well as PVK [38] with its active side-group, and conjugated polymers such as thiophene derivatives, [39,40] polybiphenyls, [41,42] poly(spirofluorene), [43] and substituted poly(phenylene vinylene). [44] Combinations of functional components have been explored as potential storage media, most commonly electron donors and acceptors, motivated by the conductive properties of organic charge-transfer complexes.…”

“…The UCLA group extended this approach to a system where the organic phase was polystyrene, either alone [72] or doped with various species, including Alq 3 , [73] 8-hydroxyquinoline, [74] and dimethylanthracene. [74] It should be recognized that, in many of these systems, the metallic NPs are coated, either with a layer of native oxide (e.g., the Al particles of our group [70] and Ma et al [71] ) or with a colloid stabilizer, for example, Au with triphenylphosphine [41,42] and Au with dodecanethiol, [73,74] or with an electron donor, for example, Au with naphthalenethiol. [72,74] Conjugated polymers have been used as the hosts, namely poly(3-hexylthiophene) containing Au-dodecanethiol [75] or carbon nanotubes.…”

A concise review on microwave-assisted polycondensation reactions and curing of polycondensation polymers with focus on the effect of process conditions

“…Synthesis of poly(biphenylmethylene)s, derived from bistriflates of bisphenol-type monomers, by Ni(0)-mediated polymerization was studied by Beinhoff et al [44]. Reduction in reaction time from hours to minutes was observed; the studies, however, were carried out at different temperatures.…”

Distyrylbenzene-based segmented conjugated polymers: Synthesis, thin film morphology and chemosensing of hydrophobic and hydrophilic nitroaromatics in aqueous media

“…In this context, an efficacious concept of macromolecular design aiming to customize the physical and electronic properties of conjugated polymers consists in the regular insertion in the polymer backbone of atomic or molecular motifs which tailor the π-conjugation length. Thus, a variety of regularly segmented conjugated polymers (SCPs) have been synthesized by linking aromatic segments of discrete size with spacers such as biphenylene [8], binaphthylene [9], paracyclophane [10], linear alkylene [11,12] and oxyethylene chains [13], oxygen atoms [14], silicon atoms [15,16] and sp 3 -carbon atoms of the norbornylene [17], fluorenylidene [18] and isopropylidene groups [19][20][21] all of which break conjugation in a controlled manner.…”