Nomenclature of Regular Double-Strand (Ladder and Spiro) Organic Polymers

Metanomski, W. V.; Bareiss, Rolf E.; Kahovec, Jaroslav; Loening, Kurt; Shi, Lei; Шибаев, В. П.

doi:10.1515/iupac.65.0031

Cited by 5 publications

(3 citation statements)

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“…40−42 The parent−daughter conjugates are ladder-type polymers denoted with a single set of brackets that span both repeat units, according to IUPAC rules. 43 Before TROM, the compound C 3 displays a single MALDI peak at m/z 1286.8, in agreement with the theoretical exact mass of 1286.6 (Figure 5). It is typical for poly(thiophene)s to show only the molecular ion by MALDI since the desorption− ionization process is efficient via charge transfer, and thus cationization salts are not needed.…”

Section: ■ Results and Discussionsupporting

confidence: 84%

Templated Ring-Opening Metathesis (TROM) of Cyclic Olefins Tethered to Unimolecular Oligo(thiophene)s

Zhou

Palermo

2018

Macromolecules

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We developed a fully abiotic approach to template the synthesis of discrete unimolecular polyolefins. Discrete, unimolecular oligo(thiophene)s with alternating sequence were obtained by iterative convergent/divergent couplings and then functionalized with pendant cyclic olefin monomers in the side chains. Upon treatment with the Grubbs third-generation catalyst in dilute solution (0.15 mM in DCM at 0 °C), the pendant monomers undergo templated ring-opening metathesis (TROM). Then, the daughter olefin is liberated from the parent thiophene by hydrolysis. Cyclooctenes undergo TROM to afford macrocyclic products that exactly replicate the chain length of the parent oligomer, as evidenced by MALDI MS/MS and NMR. Norbornene derivatives also undergo TROM and replicate unimolecular chain lengths, but in contrast, they exclusively form the linear oligomeric products with styrenic end groups. A template that was functionalized with one norbornene unit at the α chain end, followed by five cyclooctene units along the template, underwent TROM to afford the macrocyclic daughter olefin. Intertemplate metathesis is suppressed by tuning the concentration and reaction time. Using this strategy, we can effectively replicate the unimolecular nature of a template, made by labor-intensive iterative synthesis, to produce a discrete daughter oligomer by chain growth. We also demonstrate that the templates are recyclable upon hydrolytic cleavage of daughter oligomer, attachment of fresh daughter monomer, and repetition of the TROM process.

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Section: ■ Results and Discussionsupporting

confidence: 84%

Templated Ring-Opening Metathesis (TROM) of Cyclic Olefins Tethered to Unimolecular Oligo(thiophene)s

Zhou

Palermo

2018

Macromolecules

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“…Another interesting aspect for applications includes reversible polymer networks [67,68], and most notably, graphene, as a "material of the future" that shows unusual thermomechanical properties [69]. Recently, with the rapidly growing perspective of exploiting bio-polymers as functional materials [70,71] the stability of such materials has become an issue of primary concern [72,73] as, e.g., that of double-stranded polymer decomposition [74]. Most theoretical and computational investigations have been focused on degradation of polymer chains with one-dimensional (1D) topological connectivity [75,76,77,78,79,80,81].…”

Section: After the Scan Inmentioning

confidence: 99%

An Adaptation of the Hoshen-Kopelman Cluster Counting Algorithm for Honeycomb Networks

Popova

2015

SJC

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We develop a simplified implementation of the Hoshen-Kopelman cluster countingalgorithm adapted for honeycomb networks.In our implementation of the algorithm we assume that all nodes in the networkare occupied and links between nodes can be intact or broken. The algorithm counts how many clusters there are in the network and determineswhich nodes belong to each cluster. The network information is stored intotwo sets of data. The first one is related to the connectivity of the nodes andthe second one to the state of links. The algorithm finds all clusters in onlyone scan across the network and thereafter cluster relabeling operates on avector whose size is much smaller than the size of the network. Countingthe number of clusters of each size, the algorithm determines the clustersize probability distribution from which the mean cluster size parameter canbe estimated. Although our implementation of the Hoshen-Kopelman algorithmworks only for networks with a honeycomb (hexagonal) structure, itcan be easily changed to be applied for networks with arbitrary connectivitybetween the nodes (triangular, square, etc.).The proposed adaptation of the Hoshen-Kopelman cluster counting algorithmis applied to studying the thermal degradation of a graphene-like honeycombmembrane by means of Molecular Dynamics simulation with a Langevin thermostat.ACM Computing Classification System (1998): F.2.2, I.5.3.

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“…Ladder polymers consist of conformationally restrictive fused rings in their backbones. 1,2 This unique architecture leads to many intriguing properties. Most notably, ladder polymers with rigid and densely contorted backbones experience frustrated chain packing in the bulk, leading to substantially higher fractional free volume (FFV) compared to traditional single-stranded polymers.…”

Section: ■ Introductionmentioning

confidence: 99%

Tuning the Molecular Weights, Chain Packing, and Gas-Transport Properties of CANAL Ladder Polymers by Short Alkyl Substitutions

et al. 2019

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We used catalytic arene–norbornene annulation (CANAL) polymerization to synthesize high-molecular-weight (degree of polymerization 500–800 based on M n) rigid ladder polymers with methyl, ethyl, and isopropyl substituents that can form self-standing films. The short alkyl substitution on CANAL ladder polymers significantly impacted gas-transport properties and their chain packing as revealed by variable-temperature pure-gas permeation and high-pressure sorption experiments as well as wide-angle X-ray scattering. Interestingly, a combination of methyl and isopropyl substituents enhanced both the sorption capacity and permeation of all gases tested without compromising permselectivity. Our findings suggest that varying short alkyl substitutions on ladder polymers with high fractional free volume represents an effective strategy to tune their chain packing and fractional free volume, which can enhance permeability without compromising permselectivity.

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Nomenclature of Regular Double-Strand (Ladder and Spiro) Organic Polymers

Cited by 5 publications

References 1 publication

Templated Ring-Opening Metathesis (TROM) of Cyclic Olefins Tethered to Unimolecular Oligo(thiophene)s

Templated Ring-Opening Metathesis (TROM) of Cyclic Olefins Tethered to Unimolecular Oligo(thiophene)s

An Adaptation of the Hoshen-Kopelman Cluster Counting Algorithm for Honeycomb Networks

Tuning the Molecular Weights, Chain Packing, and Gas-Transport Properties of CANAL Ladder Polymers by Short Alkyl Substitutions

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