Electrochemical oxidation of double-stranded polybisnorbornenes containing linearly aligned ferrocene linkers

Lin, Chih-Peng; Yang, Hui‐Chun; Lin, Neng-Yu; Hsu, I‐Jui; Wang, Yu; Luh, Tien‐Yau

doi:10.1039/b808958b

Cited by 24 publications

(18 citation statements)

References 31 publications

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“…To facilitate the imaging, the sample was subjected to shear treatment [16] immediately after it was dropcast on the freshly cleaved surface of highly ordered pyrolytic graphite. A typical image of polymer 2 d, which is a prototype for this series of polynorbornenes, is displayed in Figure 2 and shows a long-range ordered pattern with stripes significantly longer than the apparent length of 2 d. Such an assembly is common for double-stranded polybisnorbornenes [10,11] and is ascribed to intermolecular interactions, such as p-p stacking between terminal groups along the longitudinal dimension and van der Waal interactions between the polymeric backbones and pendant groups in the horizontal direction. The aligned stripes have a uniform width of around 5 nm.…”

Section: Resultsmentioning

confidence: 99%

“…[10] Electrochemical and magnetic investigations of these double-stranded polymers showed that there are strong interactions between the ferrocene linkers due to their close proximity. [11] It is envisaged that the incorporation of porphyrin pendants in polynorbornenes would provide an intriguing model in which all porphyrin moieties would be aligned in a similar direction and that interactions between these pendant macrocyclic aromatic rings might offer intriguing photophysical behavior. Herein we wish to report the synthesis and photophysical properties of porphyrin-appended polynorbornenes.…”

Section: Abstract: Arylpyrrolidenesmentioning

confidence: 99%

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Coherently Aligned Porphyrin‐Appended Polynorbornenes

Wang

Liu

Chen

et al. 2009

Chemistry A European J

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Six different kinds of coherently aligned porphyrin-appended polynorbornenes derived from 5,6-endo-fused N-arylpyrrolidenonorbornenes have been synthesized. Pi-pi interactions between the pendant groups are essential for dictating the photophysical properties of the polymers and the mechanism for the stereoselective formation of polymers. Splitting of the Soret band of polymers 2a-c, which have alkyl-substituted porphyrin pendant groups, suggests strong exciton coupling between chromophores. No splitting of the Soret band is observed for polymers 2d-f, which have tetraaryl substituents on the porphyrin moiety. Significant fluorescence quenching is found in polymers 2a-e, whereas only slightly reduced quantum yield is observed for 2f. Time-resolved fluorescence measurements also indicate a similar trend. The AFM image of 2d on graphite shows aggregation to form a two-dimensional, ordered pattern.

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Section: Resultsmentioning

confidence: 99%

Section: Abstract: Arylpyrrolidenesmentioning

confidence: 99%

Coherently Aligned Porphyrin‐Appended Polynorbornenes

Wang

Liu

Chen

et al. 2009

Chemistry A European J

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“…Our recent advances in the development of single-and double-stranded oligonorbornenes, [50] for example, analogues of 1 (Scheme 1), provide a unique platform for the exploration of enhanced nonlinear optical properties, [51,52] electron transfer propagating along the linearly aligned redox linkers, [53] template-directed replication of complementary oligonorbornenes, [3] oligomeric chirality, [5] and fundamental stereochemistry. [4,54,55] However, it is puzzling that submicron-long strings are sometimes observed from dropcast films.…”

Section: Introductionmentioning

confidence: 99%

Oligomeric Tectonics: Supramolecular Assembly of Double‐Stranded Oligobisnorbornene through π–π Stacking

Lee

Lin

Liao

et al. 2009

Chemistry A European J

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Self-assembly at the molecular level in solutions or on a surface is a subject of current interest. Herein we describe the tailoring of oligobisnorbornene 1, which represents an innovative concept of a preorganized building block on the tens of nanometer scale. The rodlike 1 has vinyl and styrenyl end groups. Scanning tunneling microscopy (STM) reveals that the oligomers aggregate anisotropically along the long axis and form a one-dimensional assembly in which, remarkably, no interstitial gap appears between neighboring oligomers. Dynamic light-scattering (DLS) measurements indicate that the assembly develops in solution. With a shear treatment for dropcast films, a unidirectionally ordered domain with a defect density less than 0.5 % can be prepared. Simulation results by molecular dynamics suggest that there may be multiple interactions such as pi-pi stacking and dipolar attractions taking place between the termini of the oligomers. To demonstrate the importance of double bonds in the oligomeric backbones and termini towards the tectonic assembly, a hydrogenated analogue was synthesized; pi-pi interactions are thus less significant and the film morphology is completely different from that of 1. This work extends the concept of molecular tectonics to preorganized oligomers and opens up a new avenue of nanopatterning toward nanodevices.

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“…For example, ROMP of 2,3‐ bis (trifluoromethyl)‐norbornadiene using an appropriate Schrock Mo‐carbene catalyst gave tactic all trans polymers that exhibited a much higher relaxed dielectric constant than that of the analogous 50:50 cis/trans atactic polymers prepared using the classical WCl 6 /SnMe 4 initiator system or a polymer with high cis content . Yang et al has paid more attention to polymerizing a rigid norbornene monomer catalyzed by Grubbs' catalyst to get tactic polymer. The enhanced hyperpolarizability of the high trans polymers obtained from the pyrrolidine type monomers bearing conjugated dipolar substituents was believed to result from the alignment of the chromophores.…”

Section: Introductionmentioning

confidence: 99%

Polymeric microstructures and dielectric properties of polynorbornenes with 3,5-bis(trifluoromethyl)biphenyl side groups by ring-opening metathesis polymerization

You

Song

Zhang

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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exo‐Polynorbornenes containing bis(trifluoromethyl)biphenyl side groups were synthesized by ring‐opening metathesis polymerization using different Grubbs' catalysts, the microstructures of the polymer chains were established using NMR and IR spectroscopy. The influence of monomer and catalyst structures on chain microstructure was revealed and the correlation of properties with microstructure was investigated in detail. The exo‐poly(N‐3,5‐bis(trifluoromethyl)biphenyl‐norbornene‐pyrrolidine) (exo‐PTNP) and exo‐poly(N‐3,5‐bis(trifluoromethyl)biphenyl‐norbornene‐dicarboximide) (exo‐PTNDI) formed using Ru‐I show a trans double bond bias of 67% and 83%, respectively, whereas the corresponding polymers formed using Ru‐III have lower contents of trans double bond, 30% and 50%, respectively. Compared to the highly trans endo‐PTNP formed using Ru‐I, which is isotactic and has a dielectric constant of about 20, the endo‐PTNP formed using Ru‐III, the exo‐PTNDIs and the exo‐PTNPs formed using Ru‐I and Ru‐III all have different proportions of trans and cis double bonds, they are atactic and display relatively low dielectric constants, in the range 6 to 9. DSC measurements indicate some dependence of Tg, varying 161 to 221 °C, on tacticity and cis/trans ratios with higher trans contents tending towards higher Tg. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 4786–4798

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Electrochemical oxidation of double-stranded polybisnorbornenes containing linearly aligned ferrocene linkers

Cited by 24 publications

References 31 publications

Coherently Aligned Porphyrin‐Appended Polynorbornenes

Coherently Aligned Porphyrin‐Appended Polynorbornenes

Oligomeric Tectonics: Supramolecular Assembly of Double‐Stranded Oligobisnorbornene through π–π Stacking

Polymeric microstructures and dielectric properties of polynorbornenes with 3,5-bis(trifluoromethyl)biphenyl side groups by ring-opening metathesis polymerization

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