Optically active vinyl polymers containing fluorescent groups, 2. Synthesis of optically active vinyl carbazole derivatives

Chiellini, Emo; Solaro, Roberto; Ledwith, A.

doi:10.1002/macp.1977.021780307

Cited by 16 publications

(4 citation statements)

References 20 publications

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“…The intensity of CD signals of the presently investigated polymers is larger than those observed in previously reported optically active vinylic polymers containing carbazole, where the chiral residues were not directly linked to the main-chain. [18][19][20][21] Furthermore, in agreement with the polarimetric data (Table 3), the intensity of the CD bands appears much higher in the polymers than in the corresponding monomers, thus indicating that the presence of an optically active cyclic residue of one prevailing absolute configuration, interposed between the main chain of the polymer and the carbazole chromophore, favors the establishment of conformational dissymmetry in the macromolecules and higher chiral perturbation on the electronic transitions of the carbazole chromophore.…”

Section: Chiroptical Propertiessupporting

confidence: 71%

“…[8][9][10][11][12][13][14][15] In this context, stereoregular helical polyacetylenes containing in the side chain the carbazole group functionalized with chiral minidendrons and with chiral menthyl, bornyl and triphenylamine groups [15][16][17] and optically active vinyl homo-and copolymers with side chain carbazole moieties [18][19][20][21] have been reported. Differently from polyacetylenes, polymers with saturated hydrocarbon main chain do not exhibit in the circular dichroism (CD) spectra any skeletal chromophore band directly connected to the type of conformational order of the macromolecules, the unique source of information deriving from the CD signals related to side-chain chromophores.…”

Section: Full Papermentioning

confidence: 99%

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Methacrylic Polymers Containing Optically Active Side‐Chain Carbazole: Synthesis, Characterization and Photoconductive Properties

Angiolini

Benelli

Giorgini

et al. 2008

Macro Chemistry & Physics

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Two novel optically active polymethacrylates bearing in the side chain a cyclic chiral group of one prevailing absolute configuration linked to the carbazole chromophore, deriving from the related monomers (S)‐(−)‐3‐methacryloyloxy‐N‐[3‐(9‐ethylcarbazolyl)]pyrrolidine [(S)‐(−)‐MECP] and (S)‐(+)‐2‐methacryloyloxy‐N‐[3‐(9‐ethylcarbazolyl)]succinimide [(S)‐(+)‐MECSI], have been prepared and characterized with the aim to obtain materials suitable to photoconductive applications. Poly[(S)‐(−)‐MECP] and poly[(S)‐(+)‐MECSI] exhibit remarkable thermal stability, with glass transition temperature around 200 °C and decomposition temperatures in the range 330–350 °C. Spectroscopic, thermal and chiroptical characterizations indicate the occurrence of dipolar interactions among the side chain moieties and the presence of chiral conformation at least for chain segments of the macromolecules. The photoconductive properties are discussed in terms of extent of conjugation in the side chain based on the electron‐acceptor or electron‐donator properties of the optically active ring linked to the carbazole group.magnified image

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Section: Chiroptical Propertiessupporting

confidence: 71%

Section: Full Papermentioning

confidence: 99%

Methacrylic Polymers Containing Optically Active Side‐Chain Carbazole: Synthesis, Characterization and Photoconductive Properties

Angiolini

Benelli

Giorgini

et al. 2008

Macro Chemistry & Physics

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“…Die polymeren optisch aktiven Acetale 7 b wurden analog den polymeren 9-Isobutylcarbazol-3aldehydacetalen 7 a hergestellt. Zur Synthese von 7 b (39) und 7 b (49) wurde 3-Forrnyl-9-((S)-2-methylbuty1)carbazol mit einem spezifischen Drehwert [a]g = -8,515 (Chloroform) eingesetzt, fur die Herstellung von 7 b (43) und 7 b (47) wurde der optisch aktive Aldehyd mit [a]? = -8,17 (Chloroform) verwendet.…”

Section: Partielle Acetalkierung Von Polyvinylalkohol Rnit 3-formyl-9unclassified

“…= -8,17 (Chloroform) verwendet. Die polymeren Acetale 7 b (39), 7 b (43) und 7 b (49) waren unloslich in Dichlormethan und wurden deshalb wie oben beschrieben in Essigsiiureanhydrid umgesetzt.…”

Section: Partielle Acetalkierung Von Polyvinylalkohol Rnit 3-formyl-9unclassified

Polymere charge‐transfer‐komplexe auf der basis von polyvinylalkoholacetalen, 4

Geißler

Schulz

1982

Makromol. Chem.

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Partially acetalisized poly(viny1 alcoho1)s with degrees of acetalization between 39 and 60% were prepared by reaction of poly(viny1 alcohol) with 9-isobutyl-3-carbazolealdehyde (5 a) or 3-formyl-9-((S)-2-methylbutyl)carbazole (5b). Complex formation constants and &-values of the charge-transfer complexes with ethylenetetracarbonitrile, 2,5-cyclohexadien-1 ,Cdiylidenedimalonodinitrile, 2,4,5,7-tetranitro-9-fluorenone, and 2,4,7-trinitro-9-fluorenone were determined. Circular dicroism measurements of the optically active CT-complexes indicate two distinct CT-transitions. Die polymeren DonatorenIn Fortfuhrung friiherer Arbeiten uber polymere CT-Komplexe 3, wurden zwei neue polymere Donatoren synthetisiert mit 2-(9-Isobutyl-3-carbazolyl)-1,3-dioxan-4,6-diylmethylen-und Hydroxyethylen-Einheiten (7a) bzw. Acetoxy-Einheiten (8a) und mit 2-[9-((S)-2-Methylbutyl)-3-carbazolyl]-l,3-dioxan-4,6-diylmethylen-und Hydroxyethylen-Einheiten (7b) bzw. Acetoxy-Einheiten (8b).Ausgangsprodukt zur Synthese der polymeren Acetale war Isobutanol (la) bzw. (S)-2-Methyl-l-butanol (lb) (Optische Reinheit: 95,4%). Die Alkohole wurden mit Phosphortribromid in die entsprechenden Alkylbromide 2a bzw. 2b iiberfiihrt. Diese dienten zur Alkylierung von Carbazol. Die 9-Alkylcarbazole 4a bzw. 4b wurden durch eine Vilsmeyer-Reaktion zu den 9-Alkyl-3-carbazolaldehyden 5a bzw. 5 b umgesetzt. Diese werden mit Polyvinylalkohol (6) unter der katalytischen Wirkung von p-Toluolsulfonsaure partiell acetalisiert unter Bildung der Polymeren 7a bzw. 7b. Der aus der Elementaranalyse bestimmte Acetalisierungsgrad (AG) *) von 7a betragt 39 -6O%, der von 7 b 32 -49%. Die Polymeren sind nahezu farblose, pulverige Substanzen. Die Loslichkeit (z. B. in Dichlormethan) hangt sehr von den Reaktionsbedingungen ab. Unlosliche Produkte konnen durch Acetylierung der nicht umgesetzten Hydroxylgruppen in losliche Produkte uberfiihrt werden. a) Teil 3: cf. 3). b, Teil der Dissertation von U. GeiBler, Mainz 1979, D 77. *) Der AG (in %, ber. aus der Elementaranalyse) wird in Klammern nach der Substanzbezeichnung angegeben; z.B. 7a (44) = 7a mit einem AG von 44%.

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Resolution of racemic carboxylic acids via the lipase-catalyzed irreversible transesterification of vinyl esters

et al. 1999

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The lipase‐catalyzed irreversible transesterification procedure using vinyl esters was applied to the resolution of racemic 2‐phenoxypropanoic acids. Aspergillus niger lipase showed high enantioselectivities and reasonable reaction rates. The enantioselectivity was found to be affected profoundly by several variables, e.g., the alcohol as nucleophile, the organic solvent used, and the reaction temperature. A gram‐scale resolution of (RS)‐2‐phenoxypropanoic acid was achieved after optimization of the reaction conditions. Then this irreversible transesterification procedure was applied to the resolution of some related 2‐substituted carboxylic acids. Thus, racemic 2‐methoxy‐2‐phenylacetic acid was resolved via the A. niger lipase‐catalyzed transesterification of the corresponding vinyl ester. 2‐Phenylpropanoic acid and 2‐phenylbutanoic acid were resolved using Pseudomonas sp. lipase. A gram‐scale resolution of 2‐phenylbutanoic acid was achieved by this procedure coupled with the porcine liver esterase‐catalyzed hydrolysis of the resulting methyl ester. Chirality 11:554–560, 1999. © 1999 Wiley‐Liss, Inc.

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Optically active vinyl polymers containing fluorescent groups, 2. Synthesis of optically active vinyl carbazole derivatives

Abstract: Synthesis and characterization of (S)‐3‐sec‐butyl‐9‐vinylcarbazole (7), (S)‐9‐(2‐methylbutyl)‐2‐vinylcarbazole (14), and (S)‐9‐(2‐methylbutyl)‐3‐vinylcarbazole (18) are described in detail.

Cited by 16 publications

References 20 publications

Methacrylic Polymers Containing Optically Active Side‐Chain Carbazole: Synthesis, Characterization and Photoconductive Properties

Methacrylic Polymers Containing Optically Active Side‐Chain Carbazole: Synthesis, Characterization and Photoconductive Properties

Polymere charge‐transfer‐komplexe auf der basis von polyvinylalkoholacetalen, 4

Resolution of racemic carboxylic acids via the lipase-catalyzed irreversible transesterification of vinyl esters

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