High glass transition temperature chromophore functionalised poly(phenylquinoxalines) for nonlinear optics

Gubbelmans, Elke; Broeck, Katleen Van den; Verbiest, Thierry; Beylen, Marcel Van; Persoons, André; Samyn, Celest

doi:10.1016/s0014-3057(02)00307-5

Cited by 12 publications

(3 citation statements)

References 33 publications

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“…[14][15][16][17] In one report [14] DCM derivatives were used in the synthesis of high glass transition temperature (T g ) poly(phenylquinoxalines). Anyway those systems contain the NLO chromophore only in low weight amount leading to a modest NLO activity.…”

Section: Introductionmentioning

confidence: 99%

NLO Behavior of Polymers Containing Y‐Shaped Chromophores

Carella

Borbone

Caruso

et al. 2007

Macro Chemistry & Physics

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New polyurethanes containing Y‐shaped chromophores, symmetrical derivatives of 4‐(dicyanomethylene)‐2‐methyl‐6‐[p‐(dimethylamino)styryl]‐4H‐pyran, have been prepared. The polymers show high glass transition temperatures (Tg) and a good thermal stability. SHG measurements on poled polymer films of the synthesized polymers have been carried out and a maximum d33 of 15 pm · V−1 has been found at 1 368 nm fundamental wavelength. Time stability measurements on the most active polymer have shown that after the initial fast relaxation, the d33 value remains constant at 80 °C for 60 d.magnified image

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Section: Introductionmentioning

confidence: 99%

NLO Behavior of Polymers Containing Y‐Shaped Chromophores

Carella

Borbone

Caruso

et al. 2007

Macro Chemistry & Physics

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“…Poly(phenylquinoxaline)s (PPQs) are a well-known class of π-electron-deficient, aromatic heterocyclic polymers, which possess many desirable properties such as good processability, high glass transition temperatures, and excellent thermomechanical properties . Recently, they have also received increasing attention for the possible uses in nonlinear optical and optoelectronic devices such as the electron transport layers in light-emitting diodes . For example, a PPQ that contains thiophene segments has displayed an outstanding electron-transporting capability in the poly(phenylenevinylene)-based light-emitting devices .…”

Section: Introductionmentioning

confidence: 99%

Hyperbranched Poly(phenylquinoxaline−ether−ketone) Synthesis in Poly(phosphoric acid)/P₂O₅ Medium: Optimization and Some Interesting Observations

Baek

Tan

2006

Macromolecules

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A new self-polymerizable AB 2 monomer, 2,3-bis(4-phenoxyphenyl)quinoxaline-6-carboxylic acid, was synthesized from the double condensation reaction of 4,4′-diphenoxybenzil and 3,4-diaminobenzoic acid. It was polymerized to afford the corresponding hyperbranched poly(phenylquinoxaline) (PPQ) via a diaryl ketone formation from the Friedel-Crafts reaction of the carboxylic acid group (A) and the phenoxy ring (B) in polyphosphoric acid (PPA)/P 2 O 5 medium. The polymerization was conducted at (i) 130 and 160°C and (ii) with and without additional amounts of P 2 O 5 and monitored by analyzing the polymerization mixture sampled at certain reaction temperature and time intervals with Fourier transform infrared (FT-IR) spectroscopy and gelpermeation chromatography (GPC). Both FT-IR and GPC results corroborated our previously established optimal conditions: (i) PPA:P 2 O 5 ratio of 4:1 and (ii) efficient polymerization temperature ∼130°C. Furthermore, the series of 10 aliquots taken from the mixture prepared under the optimal conditions, precipitated into water, and stored in the vials for a month showed visually a consistent trend and a transition in the polymer densities and collectively allowed the visualization of a changeover in the macromolecular architecture from a "fanlike" conformation at the early stage of polymerization to a denser, globular conformation at higher molecular weights. The resultant hyperbranched PPQ was thermally stable with 5% weight loss at temperatures over 500°C in both air and helium atmospheres. It showed UV absorption maxima at 365-370 nm and emission maxima at 433-446 nm. The subsequent chain-end functionality conversion for the parent hyperbranched polymer could be performed in either a one-pot fashion or a two-staged process. Finally, some anomalous dilute-solution behavior (negative or "inverse" polyelectrolyte effect) was observed for the chain-end-modified hyperbranched polymers that appeared to be significantly influenced by the nature of solvents (acidic vs basic) and chain-end groups (polarity).

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“…Polyquinolines, a class of high‐performance polymer materials developed by Stille1 in the 1970s, are thermally stable and mechanically strong. Because of their excellent optical and electronic properties,2, 3 these polymers have recently been explored extensively as potentially useful materials in electronic and photonic applications, such as organic light‐emitting diodes,4–12 thin‐film transistors,13 photovoltaic cells,14 nonlinear optical devices,15–21 and optical sensors 22–24…”

Section: Introductionmentioning

confidence: 99%

Polyquinolines containing both spirobifluorene and cardofluorene units: Synthesis and characterization

Chen¹,

Shu²

2004

J. Polym. Sci. A Polym. Chem.

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We have synthesized aromatic polyquinolines containing both spirobifluorene and cardofluorene moieties in the main chain by applying acid‐catalyzed Friedländer quinoline synthesis. The incorporation of these rigid nonplanar structures into the polymer backbone, which restricts segmental mobility, significantly increases both the glass‐transition temperature and thermal stability, while providing enhanced solubility as a result of a decrease in the degree of molecular packing and crystallinity. We have also examined the optical and electrochemical properties of these polyquinolines. The low‐lying lowest unoccupied molecular orbital energy level and quasireversible electrochemical reduction of these polyquinolines suggest their potential for use as electron‐injecting/transporting materials in polymer light‐emitting diodes. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 3314–3322, 2004

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High glass transition temperature chromophore functionalised poly(phenylquinoxalines) for nonlinear optics

Cited by 12 publications

References 33 publications

NLO Behavior of Polymers Containing Y‐Shaped Chromophores

NLO Behavior of Polymers Containing Y‐Shaped Chromophores

Hyperbranched Poly(phenylquinoxaline−ether−ketone) Synthesis in Poly(phosphoric acid)/P₂O₅ Medium: Optimization and Some Interesting Observations

Polyquinolines containing both spirobifluorene and cardofluorene units: Synthesis and characterization

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High glass transition temperature chromophore functionalised poly(phenylquinoxalines) for nonlinear optics

Cited by 12 publications

References 33 publications

NLO Behavior of Polymers Containing Y‐Shaped Chromophores

NLO Behavior of Polymers Containing Y‐Shaped Chromophores

Hyperbranched Poly(phenylquinoxaline−ether−ketone) Synthesis in Poly(phosphoric acid)/P2O5 Medium: Optimization and Some Interesting Observations

Polyquinolines containing both spirobifluorene and cardofluorene units: Synthesis and characterization

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Hyperbranched Poly(phenylquinoxaline−ether−ketone) Synthesis in Poly(phosphoric acid)/P₂O₅ Medium: Optimization and Some Interesting Observations