Nonlinear and Electro-Optic Organic Devices

Lytel, R.; Lipscomb, G. F.; Thackara, J. I.; Altman, J.C.; Elizondo, P. J.; Stiller, M.; Sullivan, Brian J.

doi:10.1007/978-1-4613-0953-6_26

Cited by 10 publications

(9 citation statements)

References 9 publications

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“…The present polymerization system is well behaved and living, despite the fact that the monomer adds β to the initiator (eq 2). The evidence for this type of insertion is supported by 1 disappears and an additional resonance for H R at 12.37 ppm appears (Figure 1).…”

Section: Resultsmentioning

confidence: 84%

“…Recrystallization from diethyl ether yielded 230 mg (79.3%) of pure product. 1 Ferrocenecarboxaldehyde (50 mg, 0.24 mmol) was added to a stirred solution of the first insertion product (30 mg, 25 µmol) in C6D6 (0.5 mL). NMR investigations revealed that capping was achieved quantitatively after approximately 15 min.…”

Section: Methodsmentioning

confidence: 99%

“…Acetylenes represent important tools in polymer chemistry. Terminal as well as internal systems may serve as unique precursors for conjugated polyenes, which are a widely investigated class of π-systems in the area of nonlinear optics. − Polyynes, and among them, especially poly( p -phenyleneethynylenes), usually prepared by subsequent coupling and deprotection of terminal acetylenes, − are additionally of particular interest in the areas of liquid crystals, as well as in those of electronics and electrooptics has been reported recently.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Polyenes That Contain Mesogenic Side Chains via the Living Polymerization of 4-(Ferrocenylethynyl)-4‘-ethynyltolan

Buchmeiser

1997

Macromolecules

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The living polymerization of the metallocenyl-substituted diethynyltolan, 4-(ferrocenylethynyl)-4‘-ethynyltolan (I), by the well-defined Schrock metathesis catalyst Mo(N-2,6-i-Pr2C6H3)(CHCMe2Ph)(OCMe(CF3)2)2 (II) is described. The polymerization starts virtually solely via β-addition of the monomer to the metal−carbon double bond and yields conjugated, surprisingly soluble, main chain polyenes containing mesogenic, rigid side chains. Despite the β-addition, the polymerization proceeds in a controlled, living manner, resulting in the the formation of low polydispersity polymers. The resulting polymers exhibit a remarkable stability against air and thermal treatment.

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Section: Resultsmentioning

confidence: 84%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of Polyenes That Contain Mesogenic Side Chains via the Living Polymerization of 4-(Ferrocenylethynyl)-4‘-ethynyltolan

Buchmeiser

1997

Macromolecules

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“…Ordered polymer films with crystalline character are especially important for technological applications since they generally possess superior optical and electronic properties compared to their amorphous counterparts. In particular, interest in photonic materials , has focused a great deal of effort on the development of techniques for producing crystalline, macromolecular thin films on solid surfaces. The polymer thin film may be deposited onto a solid surface either preformed or as a monomer adlayer followed by subsequent in situ polymerization.…”

Section: Introductionmentioning

confidence: 99%

Adsorption and Polymerization of Formaldehyde on Cu(100)

Bryden

Garrett

1999

J. Phys. Chem. B

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The adsorption of formaldehyde (H2CO) on clean Cu(100) at 85 K has been studied using electron energy loss spectroscopy (EELS), X-ray photoelectron spectroscopy (XPS), and temperature-programmed desorption (TPD). For coverages up to (1.06 ± 0.22) × 1015 H2CO molecules/cm2, formaldehyde spontaneously polymerized to form a monolayer of disordered poly(oxymethylene) (POM), arranged with the chain directions parallel to the surface plane. Thermal decomposition/desorption of the polymer monolayer occurred by three routes, producing peaks in temperature-programmed desorption (TPD) at approximately 177, 200, and 215 K. The lowest temperature peak was exclusively associated with production of H2 and CO in approximately equal proportions. The two higher temperature peaks were produced by molecular H2CO generated via depolymerization of the polymer. The 200 and 215 K features displayed zero- and first-order desorption kinetics, corresponding to estimated activation energies for depolymerization of 75 ± 10 and 53.9 ± 0.5 kJ/mol, respectively. The presence of two polymer desorption peaks is attributed to chain conformational differences present within the monolayer and has not been previously observed in studies of formaldehyde adsorption on metal surfaces. Large exposures of H2CO on this surface formed multilayers of molecular formaldehyde on top of the first polymer layer. The second layer desorbed at 105 K and subsequent layers at ∼100 K.

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“…Fully conjugated polymers based on poly-ynes, poly-enynes, or poly-enes represent interesting materials for many applications in the fields of organic conductivity, − optoelectronics, and photonics. − Terminal acetylenes are polymerized preferrably by metathesis polymerization using well-defined Schrock-type metathesis catalysts to yield conjugated poly-enes. − The degree of conjugation in these materials strongly depends on the electronic as well as steric nature of the substituents in the starting alkyne. The effective conjugation length ( N eff ) describes the number of coplanar double bonds in a conjugated system.…”

Section: Introductionmentioning

confidence: 99%

Living Polymerization of Novel Conjugatively Spaced Ferrocenylacetylenes

et al. 1998

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The synthesis and living metathesis polymerization of five different conjugatively spaced ferrocenylacetylenes, (2-ethynylphenyl)ferrocene (3), (Z)-but-1-en-3-ynylferrocene (4), (E)-but-1-en-3-ynylferrocene (5), 2-(4-ethynylphen-1-yl)vin-1-ylferrocene (7), and 1-ferrocenyl-2-(4-ethynylphenyl)diazene (10) is described. Poly-10 represents the first polyacetylene containing ferrocenylazoarylene groups. The X-ray structures of two alkynes, 3 and 7, as well as of one ethynyl precursor, (4-bromophenyl)ferrocenyldiazene (8), are presented. Polymerizations of all terminal alkynes by the well-defined Schrock metathesis catalysts Mo(N−Ar‘)(CHCMe2Ph)(OCMe(CF3)2)2 (Ar‘ = 2,6-i-Pr2C6H3, 11; Ar‘ = 2,6-Me2C6H3, 12) start solely via β-addition of the corresponding monomer to the initiator except for 3, which undergoes α-addition with 12. Presumably due to metathesis-type side reactions, 4 and 5 form only low molecular weight polymers. The polymerizations of 3, 7, and 10 proceed in a strongly living manner when either initiator (11, 12) is employed. The polymers are virtually formed via solely head to tail propagation, exhibiting low polydispersities and solubility up to a degree of polymerization (DP) ≈ 60. The influence of the spacer on the final properties of the poylmers with regards to their UV−vis absorption spectra and effective conjugation lengths (N eff) is discussed.

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Nonlinear and Electro-Optic Organic Devices

Cited by 10 publications

References 9 publications

Synthesis of Polyenes That Contain Mesogenic Side Chains via the Living Polymerization of 4-(Ferrocenylethynyl)-4‘-ethynyltolan

Synthesis of Polyenes That Contain Mesogenic Side Chains via the Living Polymerization of 4-(Ferrocenylethynyl)-4‘-ethynyltolan

Adsorption and Polymerization of Formaldehyde on Cu(100)

Living Polymerization of Novel Conjugatively Spaced Ferrocenylacetylenes

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