Metathesis Polymerization of 9-(10-Hexoxycarbonyl)anthrylacetylene. A Route to a Widely Conjugated Polyacetylene with Excellent Stability and Solubility

Nomura, Ryoji; Karim, S. M. Abdul; Kajii, Hirotake; Hidayat, Rahmat; Yoshino, Katsumi; Masuda, Toshio

doi:10.1021/ma0003708

Cited by 23 publications

(14 citation statements)

References 10 publications

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“…Polymerization 4 Sn, have no activity in the polymerization of EAPAB, which is attributed to catalyst deactivation by the azo group. [23] Simultaneously, using 1,4-dioxane instead of THF as the solvent, the yield of polymerization increases and higher molecular weight polymers in lower polydispersity indices (PDI) are afforded.…”

Section: Resultsmentioning

confidence: 98%

Synthesis and Optical Properties of Poly[2‐{N‐Methyl‐N‐(4‐(4‐ethynylphenylazo)phenyl)amino}ethyl butyrate]

Yin

Fang

et al. 2005

Macro Chemistry & Physics

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Summary: The high‐molecular‐weight functional polyacetylene that contain a para‐aminoazobenzene chromophore, poly[2‐{N‐Methyl‐N‐(4‐(4‐ethynylphenylazo)phenyl)amino}ethyl butyrate] [poly(EAPAB)], was synthesized in moderate yield and characterized by FT‐IR, 1H NMR, UV‐vis, TGA, and GPC. The nonlinear optical and optical limiting properties were performed with 8 ns pulse width at 532 nm wavelength. The results show that the introduction of the flexible amino group effectively improved the solubility of polymer [poly(EAPAB)] in common organic solvent, such as CHCl3, THF, and dioxane, while poly(4‐ethynylazobenzene) [poly(4EAB)] without the flexible amino group shows poor solubility in common organic solvent. Simultaneously, poly(EAPAB) still shows good thermal stability, large third‐order nonlinear optical property, and novel optical limiting property owing to the functionalization of the para‐aminoazobenzene chromophore.

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Section: Resultsmentioning

confidence: 98%

Synthesis and Optical Properties of Poly[2‐{N‐Methyl‐N‐(4‐(4‐ethynylphenylazo)phenyl)amino}ethyl butyrate]

Yin

Fang

et al. 2005

Macro Chemistry & Physics

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“…The polymerizations of 1 14 were conducted in toluene with W‐, Mo‐, and Rh‐based catalysts that were effective for the polymerization of a wide range of monosubstituted acetylenes,4, 5 and the results are summarized in Table I. W‐based catalysts, except for WOCl 4 , were active for the polymerization of 1 (runs 1–3 and 6).…”

Section: Resultsmentioning

confidence: 99%

“…It is unfortunate, however, that the poor solubility of most of these polymers prevents the formation of high molecular weight polymers with processability such as film‐forming ability 13. On the basis of this background, we recently reported the synthesis of a new substituted polyacetylene from 9‐(10‐hexoxycycarbonyl)anthrylacetylene ( 1 ; Scheme ) 14. A soluble and widely conjugated polymer was attainable by the W‐catalyzed polymerization of 1 .…”

Section: Introductionmentioning

confidence: 99%

Application of a Serum-Free Medium for the Growth of Vero Cells and the Production of Reovirus

Butler¹,

Burgener²,

Patrick³

et al. 2000

Biotechnol. Prog.

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Two strains of reovirus (serotype 1 Lang/TIL and serotype 3 Dearing/T3D) were propagated in Vero cells grown in stationary or agitated cultures in a serum-free medium, M-VSFM. Solid microcarriers (Cytodex-1) were used to support cell growth in agitated cultures with a normal doubling time of 25 h. Cell yields of 1 x 10(6) cells/mL were obtained from an inoculum of 2 x 10(5) cells/mL in 4 days in microcarrier cultures. The growth profile and cell yield was not significantly different from serum-supplemented cultures. The virus titer increased by 3-4 orders of magnitude over a culture period of 150 h. The maximum virus titer in stationary cultures reached >1 x 10(9) pfu/mL for both strains of reovirus in M-VSFM. M-VSFM also supported high viral yields in microcarrier cultures. Both the specific productivity and final viral yield was higher in M-VSFM than serum-supplemented cultures. The high viral productivity suggests that this is a suitable system for the production of reovirus as an oncolytic agent for human therapeutic use.

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“…Sone found that the third-order nonlinear optical coefficient of trans-poly[o-trifluoromethyl(phenylacetylene)] film prepared by Mo catalyst is about two times larger than its cis-counterpart synthesized by Rh catalyst [7]. Masuda found that substituents on the ortho-positions of the phenyl rings of poly(phenylacetylene)s [7][8][9] and incorporation of bulky and planar aromatic rings such as carbazole, naphthalene, or anthracene into the polyacetylene main chains [10][11][12] can effectively improve the third-order nonlinear optical susceptibilities of the resulting polymers. Schuling once found that the third-order nonlinear optical susceptibility (g) depends on g 0 e , a term related to the movement of electron, and b, the second-order nonlinear optical susceptibility [13].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and optical properties of azobenzene-containing poly(1-alkyne)s with different spacer lengths and ring substituents

Yin

et al. 2005

Polymer

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Poly(1-alkyne)s containing azobenzene pendants with different spacer lengths and ring substitutents-{HCaC[(CH 2) m COO-C 6 H 4-NaN-C 6 H 4-NO 2 ]} n-P1(m) mZ3, 8 and-{HCaC[(CH 2) m COO-C 6 H 3-o-Br-NaN-C 6 H 4-NO 2 ]} n-P2(m) mZ3, 8} are designed and synthesized. The polymers are prepared in satisfactory yields with high molecular weights (M w up to 3.3!10 4 Da) by [Rh(nbd)Cl] 2-Et 3 N in THF or dioxane. Their structures and properties are characterized and evaluated by IR, UV, NMR, TGA, nonlinear optical and optical limiting analyses. All the polymers are completely soluble in common organic solvents and lose 5% of their weights at temperatures of w270 8C. The spacer length and the pendant substitutent affect the nonlinear optical and optical limiting properties of the polymers, with 1(3) showing superior properties than its counterparts 1(8) and 2(3) with long methylene spacers and bromide substitutents on the azobenzene pendants, respectively.

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Metathesis Polymerization of 9-(10-Hexoxycarbonyl)anthrylacetylene. A Route to a Widely Conjugated Polyacetylene with Excellent Stability and Solubility

Cited by 23 publications

References 10 publications

Synthesis and Optical Properties of Poly[2‐{N‐Methyl‐N‐(4‐(4‐ethynylphenylazo)phenyl)amino}ethyl butyrate]

Synthesis and Optical Properties of Poly[2‐{N‐Methyl‐N‐(4‐(4‐ethynylphenylazo)phenyl)amino}ethyl butyrate]

Application of a Serum-Free Medium for the Growth of Vero Cells and the Production of Reovirus

Synthesis and optical properties of azobenzene-containing poly(1-alkyne)s with different spacer lengths and ring substituents

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