From Polynorbornene to the Complementary Polynorbornene by Replication

Lin, Neng-Yu; Lin, Shu‐Wha; Lee, Shern‐Long; Chen, Chun‐Hsien; Hsu, Chao-Hsiung; Hwang, Lian Pin; Xie, Zhenyu; Chen, Chung-Hsuan; Huang, Shou‐Ling; Luh, Tien‐Yau

doi:10.1002/anie.200700472

Cited by 71 publications

(47 citation statements)

References 73 publications

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“…[3] As described previously, [3,4] the ferrocene moiety is employed as a linker for these double-stranded polymers because the spacing occupied by the ferrocene moiety appears to be within the limit of span for the vinylcyclopentane monomeric unit in polynorbornenes (5)(6). [3,4,51,52] It has certain rigidity but is also somewhat flexible to accommodate the pending norbornene moieties in 3 in close proximity for the polymerization process. In addition, it may serve as a kind of stuffing to prop up the two polymeric backbones.…”

Section: Resultsmentioning

confidence: 99%

“…[4,54,55] However, it is puzzling that submicron-long strings are sometimes observed from dropcast films. [3][4][5]50] Such extraordinary long features were previously ascribed to those significantly deviated from the average molecular weight. [3,4] These oligobisnorbornenes are prepared from a Grubbs I catalyst-mediated ring-opening metathesis polymerization (ROMP).…”

Section: Introductionmentioning

confidence: 96%

“…[3][4][5]50] Such extraordinary long features were previously ascribed to those significantly deviated from the average molecular weight. [3,4] These oligobisnorbornenes are prepared from a Grubbs I catalyst-mediated ring-opening metathesis polymerization (ROMP). [56,57] Depending on the quenching reagent, some of the terminal groups of the oligoAbstract: Self-assembly at the molecular level in solutions or on a surface is a subject of current interest.…”

Section: Introductionmentioning

confidence: 96%

“…To resolve this question and to explore the viability of tectonic assembly through a preorganized nanoscale building block, tailored herein is oligomeric bisnorbornene 1, [3] a ladderlike tecton that results in the facile assembly of submicron-long structures, which is indicative of significant anisotropic attractions taking place at the p-electronrich termini. The assembled stripe lines of 1 can be further patterned into a two-dimensional array that might lead to potential applications that involve nanopatterning [58][59][60] and crystal engineering.…”

Section: Introductionmentioning

confidence: 99%

“…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%

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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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