DE4339646A1 - New di:acetylene cpds. with extended pi-electron systems - Google Patents

New di:acetylene cpds. with extended pi-electron systems

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Publication number
DE4339646A1
DE4339646A1 DE19934339646 DE4339646A DE4339646A1 DE 4339646 A1 DE4339646 A1 DE 4339646A1 DE 19934339646 DE19934339646 DE 19934339646 DE 4339646 A DE4339646 A DE 4339646A DE 4339646 A1 DE4339646 A1 DE 4339646A1
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Prior art keywords
diacetylene
cpds
new
compounds according
extended
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German (de)
Inventor
Herbert Dr Naarmann
Henning Prof Dr Hopf
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BASF SE
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
    • C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
    • C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
    • C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C50/00—Quinones
    • C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
    • C07C50/30—Quinones containing groups having oxygen atoms singly bound to carbon atoms with polycyclic non-condensed quinoid structure
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F38/00—Homopolymers and copolymers of compounds having one or more carbon-to-carbon triple bonds

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Diacetylene cpds. of formula (I) and (II) are new: T = -(ch2)p- or 1,4-phenylene; Q = a gp. (i)-(iii) or reaction prods. thereof with dienes; Q' = a gp. (iv); R = H, 1-10C alkyl or halo; Z = -O-, -S or -NH-; n = 1-100; p = 1-20; q = 0 or 1; r = 1 or 2. Also claimed are films and foils obtd. from (I) and (II).

Description

Die vorliegende Erfindung betrifft Diacetylenverbindungen der allgemeinen Formel IThe present invention relates to diacetylene compounds general formula I.

oder deren Umsetzungsprodukte mit Dienen bedeutet undor their reaction products with dienes and

ist,
R Wasserstoff, C₁- bis C₁₀-Alkyl oder Halogen bedeutet,
Z -O-, -S- oder -NH- darstellt
n eine ganze Zahl von 1 bis 100,
p eine ganze Zahl von 1 bis 20,
q 0 oder 1 und
r 1 oder 2 ist. is
R is hydrogen, C₁ to C₁₀ alkyl or halogen,
Z represents -O-, -S- or -NH-
n is an integer from 1 to 100,
p is an integer from 1 to 20,
q 0 or 1 and
r is 1 or 2.

Ferner betrifft die vorliegende Erfindung deren Verwendung zum Herstellen von Polymeren.Furthermore, the present invention relates to their use for Manufacture of polymers.

Verbindungen mit einem ausgedehnten π-Elektronensystem können in zahlreichen technischen Gebieten eingesetzt werden und sind deshalb von Interesse. Bedeutsam ist auch die Anordnung der ein­ zelnen Verbindungen im Molekülverbund. So können Eigenschaften wie elektrische Leitfähigkeit von Materialien auf der Basis von Verbindungen mit einem ausgedehnten π-Elektronensystem wesentlich davon beeinflußt werden, ob diese stapelförmig vorliegen oder nicht.Compounds with an extended π electron system can be found in numerous technical fields are used and are therefore of interest. The arrangement of the one is also significant individual connections in the molecular compound. So can properties such as electrical conductivity of materials based on Connections with an extended π-electron system are essential are influenced by whether they are stacked or Not.

Aufgabe der vorliegenden Erfindung war es, neue Verbindungen zur Verfügung zu stellen, die starre Diingruppen enthalten und gute elektrische Leitfähigkeiten aufweisen.The object of the present invention was to develop new compounds To provide rigid diamine groups and good ones have electrical conductivities.

Diese Aufgabe wird von den eingangs definierten Diacetylenverbin­ dungen erfüllt.This task is performed by the diacetylene compound defined at the beginning fulfilled.

Die erfindungsgemäßen Diacetylenverbindungen haben die allgemeine Formel I oder IIThe diacetylene compounds according to the invention have the general Formula I or II

Dabei kann T einen Alkylenrest CH₂ bedeuten. Die Variable p kann eine ganze Zahl von 1 bis 20, bevorzugt 1 bis 10, besonders bevorzugt 1 bis 6 bedeuten. Insbesondere ist T Methylen oder Ethylen. Darüber hinaus kann T ein Phenylenrest sein. Q kann eine Chinon- oder substituierte Chinongruppe der folgenden Formeln darstellen:T can mean an alkylene radical CH₂. The variable p can be an integer from 1 to 20, preferably 1 to 10, particularly are preferably 1 to 6. In particular, T is methylene or Ethylene. In addition, T can be a phenylene radical. Q can be one Quinone or substituted quinone group of the following formulas represent:

Z kann -O-, -S- oder -NH- sein und die Variable q kann den Wert 0 oder 1 annehmen. Bevorzugt ist q 1. R kann Wasserstoff oder eine C₁- bis C₁₀-Alkylgruppe bedeuten. Die Alkylgruppen können sowohl linear als auch verzweigt sein. Bevorzugte Alkylgruppen sind li­ near und haben 1 bis 4 Kohlenstoffatome, wie Methyl, Ethyl, n-Propyl oder n-Butyl. Daneben kann R auch für ein Halogen, bevor­ zugt Chlor stehen. Besonders bevorzugt ist R Wasserstoff. Die Va­ riable r kann den Wert 1 oder 2 annehmen. Weiterhin kann Q einen Maleinsäureimidrest bedeuten oder einen Triazolindionrest dar­ stellen, deren Formeln unten aufgeführt sind:Z can be -O-, -S- or -NH- and the variable q can have the value 0 or accept 1. Q is preferred. R can be hydrogen or a C₁- to C₁₀ alkyl group. The alkyl groups can both be linear as well as branched. Preferred alkyl groups are li near and have 1 to 4 carbon atoms, such as methyl, ethyl, n-propyl or n-butyl. In addition, R can also be used for a halogen before  adds chlorine to stand. R is particularly preferably hydrogen. The Va riable r can have the value 1 or 2. Furthermore, Q can be a Maleimide or a triazolinedione residue whose formulas are listed below:

Der Rest Q′ stellt eine substituierte PerylengruppeThe rest Q 'represents a substituted perylene group

dar. Die Variable n kann eine ganze Zahl von 1 bis 100, bevorzugt 2 bis 50, insbesondere 2 bis 10 sein.The variable n can be an integer from 1 to 100, preferably 2 to 50, in particular 2 to 10.

Die Diacetylenverbindungen, in denen Q ein Chinon- oder substi­ tuierter Chinonrest ist, können beispielsweise ausgehend von OH-, NaS- oder NH₂-substituierten Alkinen durch Umsetzen mit Halogen­ chinonen zu Monoalkinverbindungen und anschließender oxidativer Kupplung beispielsweise in Gegenwart von Kupfer-I-salzen herge­ stellt werden. Entsprechend lassen sich die Diacetylenverbindun­ gen, in denen Q ein Maleinsäureimid- oder Triazolindionrest ist, aus mit einer Aminogruppe substituierten Alkinen durch Umsetzen mit Maleinsäureanhydrid oder Urazolen und anschließender oxidati­ ver Kupplung herstellen. Die oxidative Kupplungsreaktion von Al­ kinen zu Diacetylenen ist allgemein bekannt. An dieser Stelle sei beispielsweise auf Synthetic Metals 48 (1992) 296 und die dort zitierte Literatur verwiesen. Die so erhaltenen Diacetylenverbin­ dungen I können als Dienophile mit Dienen wieThe diacetylene compounds in which Q is a quinone or substi is quinone residue, for example starting from OH, NaS- or NH₂-substituted alkynes by reaction with halogen quinones to monoalkyne compounds and subsequent oxidative Coupling, for example, in the presence of copper (I) salts be put. The diacetylene compounds can be genes in which Q is a maleimide or triazolinedione residue, from alkynes substituted with an amino group by reaction with maleic anhydride or urazoles and subsequent oxidati Make the coupling. The oxidative coupling reaction of Al Kinetic to diacetylenes is well known. At this point for example on Synthetic Metals 48 (1992) 296 and those there literature cited. The diacetylene compound thus obtained I can serve as dienophiles with services like

oder
Perylen zu weiteren Diacetylenverbindungen I oder II umgesetzt werden.or
Perylene to further diacetylene compounds I or II are implemented.

Als Beispiele für bevorzugte Diacetylenverbindungen I sind zu nennen,Examples of preferred diacetylene compounds I include call,

Diese Umsetzung erfolgt im allgemeinen bei Temperaturen von 0 bis 100°C, bevorzugt bei 20 bis 50°C bei Atmosphärendruck oder erhöh­ ten Drücken, z. B. bis zu 10 kbar. Vorzugsweise wird die Reaktion in einem unter den Bedingungen inerten Lösungsmittel wie Toluol oder Petrolether durchgeführt. Es ist auch möglich, das Dien oder das Dienophil auf einer Matrix, beispielsweise Glas oder Aluminium als dünne Schicht von beispielsweise 0,1 nm bis 0,1 mm aufzubringen und das Dienophil bzw. Dien im Vakuum bei Drücken von bis zu 10-6 Torr aufzudampfen und zur Reaktion zu bringen.This reaction is generally carried out at temperatures from 0 to 100 ° C, preferably at 20 to 50 ° C at atmospheric pressure or elevated pressures, for. B. up to 10 kbar. The reaction is preferably carried out in a solvent which is inert under the conditions, such as toluene or petroleum ether. It is also possible to apply the diene or the dienophile on a matrix, for example glass or aluminum, as a thin layer of, for example, 0.1 nm to 0.1 mm and the dienophile or diene in vacuo at pressures of up to 10 -6 torr evaporate and react.

Die so erhaltenen Diacetylenverbindungen lassen sich thermisch oder indem sie Strahlung ausgesetzt werden zu den erfindungs­ gemäßen Polymeren umsetzen. In der Regel können die Diacetylen­ verbindungen bei Temperaturen von 50 bis 180°C, bevorzugt von 75 bis 120°C polymerisiert werden. Ebenso können Laser- oder Röntgen­ strahlung aber auch Sonnenlicht oder das Licht von Neon- oder Quecksilberlampen zur Herstellung der Polymeren verwendet werden.The diacetylene compounds thus obtained can be thermally or by being exposed to radiation to the invention implement appropriate polymers. As a rule, the diacetylene compounds at temperatures from 50 to 180 ° C, preferably from 75 polymerized up to 120 ° C. Laser or X-ray can also be used radiation but also sunlight or the light of neon or Mercury lamps are used to make the polymers.

Die erfindungsgemäßen Diacetylenverbindungen eignen sich z. B. zum Herstellen opto-elektronischer Bauelemente oder von Sensoren. The diacetylene compounds according to the invention are suitable, for. B. for the manufacture of opto-electronic components or sensors.  

BeispieleExamples Beispiel 1example 1 Synthese von Bis-1,6(2′-thio-2′,5′-cyclohexa­ dien-1′,4′-dion)-2,4-hexadiin (I₂)Synthesis of bis-1,6 (2′-thio-2 ′, 5′-cyclohexa dien-1 ′, 4′-dione) -2,4-hexadiin (I₂)

1,42 g (0,1 Mol) 2-Chlorchinon und 0,94 g (0,1 Mol) Natriumpro­ pargylsulfid wurden in 100 ml Dimethylformamid gelöst und drei Stunden bei 100°C erhitzt. Das so erhaltene Produkt (Ausbeute des Rohproduktes 1,7 g) wurde durch Waschen mit Wasser gereinigt und getrocknet.1.42 g (0.1 mol) 2-chloroquinone and 0.94 g (0.1 mol) sodium pro pargyl sulfide were dissolved in 100 ml of dimethylformamide and three Heated at 100 ° C for hours. The product thus obtained (yield of Crude product 1.7 g) was cleaned by washing with water and dried.

Anschließend wurden 1,78 g (0,1 Mol) des monomeren Chinonpro­ pinthioether mit 200 mg Kupfer(I)chlorid und 2 ml N,N,N′,N′-Te­ tramethylendiamin in 100 ml Aceton versetzt. Bei Raumtemperatur wurde 2 Stunden lang ein Sauerstoffstrom von 1 l/min durch die Reaktionsmischung geleitet. Anschließend wurde das dimere Hexa­ diinderivat im Rotationsverdampfer eingeengt und durch Säulen­ chromatographie an Kieselgel (Laufmittel: Toluol/Aceton 1 : 1 (v/v)) gereinigt. Ausbeute 3,1 g (87,6% d. Th.).Then 1.78 g (0.1 mol) of the monomeric quinone pro pinthioether with 200 mg copper (I) chloride and 2 ml N, N, N ′, N′-Te tramethylenediamine in 100 ml acetone. At room temperature an oxygen flow of 1 l / min through the Reaction mixture passed. Then the dimeric hexa diindivative concentrated in a rotary evaporator and through columns chromatography on silica gel (eluent: toluene / acetone 1: 1 (v / v)) cleaned. Yield 3.1 g (87.6% of theory).

Polymerisation von I₂Polymerization of I₂

Eine 1 gew.-%ige Lösung von I₂ in Dimethylformamid wurde auf Quarzplättchen (3 × 3 cm) aufgebracht. Das Lösungsmittel wurde im Vakuum entfernt. Anschließend wurden die beschichteten Quarz­ plättchen auf 120°C erwärmt oder in einem ADUR-Flachbeschichter, mit 7 × 40 W Leuchten bei 350 nm 5 min lang belichtet.A 1 wt .-% solution of I₂ in dimethylformamide was on Quartz plates (3 × 3 cm) applied. The solvent was in Vacuum removed. Then the coated quartz platelet heated to 120 ° C or in an ADUR flat coater, exposed to 7 × 40 W lamps at 350 nm for 5 min.

Beispiel 2Example 2 Synthese von Bis-1,6(N-maleimidyl)-2,4-hexadiin 14Synthesis of bis-1,6 (N-maleimidyl) -2,4-hexadiin 14

1,35 g (0,1 Mol) des monomeren Propinderivates wurden wie unter Beispiel 1 beschrieben zu I₄ umgesetzt. Ausbeute 1,9 g (73% d. Th.).1.35 g (0.1 mol) of the monomeric propyne derivative were as below Example 1 described to I₄ implemented. Yield 1.9 g (73% of theory  Th.).

Polymerisation von I₄Polymerization of I₄

Wie unter Beispiel 1 beschrieben wurden beschichtete Quarz­ plättchen hergestellt. Beim Erwärmen auf 100°C oder Belichten konnten Polymere, die in organischen Lösungsmitteln unlöslich wa­ ren, hergestellt werden. Coated quartz was coated as described in Example 1 platelets made. When heating to 100 ° C or exposure could polymers that were insoluble in organic solvents ren, are produced.  

Beispiel 3Example 3 Synthese von Bis-1,6(4′-N-maleimidyl-phenylen)-1,3-butadiin I₅Synthesis of bis-1,6 (4'-N-maleimidylphenylene) -1,3-butadiin I₅

2,1 g (0,1 M) des monomeren Phenylacetylenderivates wurden wie unter Beispiel 1 beschrieben zu I₅ umgesetzt. Ausbeute: 2,7 g (77,6% d. Th.).2.1 g (0.1 M) of the monomeric phenylacetylene derivative were as described in Example 1 implemented to I₅. Yield: 2.7 g (77.6% of theory).

Polymerisation von I₅Polymerization of I₅

Wie unter Beispiel 1 beschrieben wurden beschichtete Quarz­ plättchen hergestellt. Beim Erwärmen auf 100°C oder Belichten konnten Polymere, die in organischen Lösungsmitteln unlöslich wa­ ren, hergestellt werden.Coated quartz was coated as described in Example 1 platelets made. When heating to 100 ° C or exposure could polymers that were insoluble in organic solvents ren, are produced.

Beispiel 4Example 4 Synthese von Bis-1,6(triazolyldion)-2,4-hexachin (I₆)Synthesis of bis-1,6 (triazolyldione) -2,4-hexachin (I₆)

Entsprechend der Vorschrift in Beispiel 2 wurde I₆ hergestellt. Die Ausbeute der Kupplungsreaktion betrug 2,2 g (81,5% d. Th.).I₆ was prepared in accordance with the instructions in Example 2. The yield of the coupling reaction was 2.2 g (81.5% of theory).

Polymerisation von I₆Polymerization of I₆

Wie unter Beispiel 1 beschrieben wurden beschichtete Quarz­ plättchen hergestellt. Beim Erwärmen auf 80°C oder Belichten konn­ ten Polymere, die in organischen Lösungsmitteln unlöslich waren, hergestellt werden.Coated quartz was coated as described in Example 1 platelets made. When heating to 80 ° C or exposure polymers that were insoluble in organic solvents getting produced.

Beispiel 5Example 5 Synthese von Bis-1,4(4′-triazolylphenylen)-1,3-butadiin (I₇)Synthesis of bis-1,4 (4′-triazolylphenylene) -1,3-butadiin (I₇)

(I₇) wurde entsprechend der in Cookson et al., J. Chem. Soc. (C) (1967), 1905-1909, für die Synthese von 4-Phenyl-1,2,4-triazo­ lin-3,4-dion angegebenen Vorschrift, ausgehend von 4-(p-Aminophe­ nyl)ethin hergestellt. Anschließend wurden 2,1 q (0,1 Mol) wie oben beschrieben oxidativ gekuppelt. Ausbeute: 3,2 g (84,2% d. Th.).(I₇) was according to the in Cookson et al., J. Chem. Soc. (C) (1967), 1905-1909, for the synthesis of 4-phenyl-1,2,4-triazo lin-3,4-dione, starting from 4- (p-aminophe nyl) ethyne produced. Then 2.1 q (0.1 mol) were like oxidatively coupled described above. Yield: 3.2 g (84.2% of theory Th.).

Polymerisation von I₇Polymerization of I₇

Wie unter Beispiel 1 beschrieben wurden beschichtete Quarz­ plättchen hergestellt. Beim Erwärmen auf 90°C oder Belichten konn­ ten Polymere, die in organischen Lösungsmitteln unlöslich waren, hergestellt werden.Coated quartz was coated as described in Example 1 platelets made. When heating to 90 ° C or exposure polymers that were insoluble in organic solvents getting produced.

Claims (7)

1. Die vorliegende Erfindung betrifft Diacetylenverbindungen der allgemeinen Formel I oder deren Umsetzungsprodukte mit Dienen bedeutet und ist,
R Wasserstoff, C₁- bis C₁₀-Alkyl oder Halogen bedeutet,
Z -O-, -S- oder -NH- darstellt
n eine ganze Zahl von 1 bis 100,
p eine ganze Zahl von 1 bis 20,
q 0 oder 1 und
r 1 oder 2 ist. 1. The present invention relates to diacetylene compounds of the general formula I. or their reaction products with dienes and is
R is hydrogen, C₁ to C₁₀ alkyl or halogen,
Z represents -O-, -S- or -NH-
n is an integer from 1 to 100,
p is an integer from 1 to 20,
q 0 or 1 and
r is 1 or 2. 2. Diacetylverbindungen nach Anspruch 1, in denen T -CH₂- oder ist.2. Diacetyl compounds according to claim 1, in which T is -CH₂- or is. 3. Diacetylenverbindungen nach Anspruch 1 oder 2, in denen Q ist.3. Diacetylene compounds according to claim 1 or 2, in which Q is. 4. Diacetylenverbindungen nach einem der Ansprüche 1 bis 3, in denen als Dien 1,4-Butadien oder Perylen verwendet wird.4. diacetylene compounds according to any one of claims 1 to 3, in which is used as diene 1,4-butadiene or perylene. 5. Verwendung der Diacetylenverbindungen gemäß einem der Ansprü­ che 1 bis 4 zum Herstellen von Polymeren.5. Use of the diacetylene compounds according to one of the claims che 1 to 4 for the production of polymers. 6. Verwendung der Diacetylenverbindungen nach einem der Ansprü­ che 1 bis 4 zum Herstellen von Filmen oder Folien.6. Use of the diacetylene compounds according to one of the claims che 1 to 4 for the production of films or foils. 7. Filme oder Folien erhältlich aus den Diacetylenverbindungen gemäß einem der Ansprüche 1 bis 4.7. Films or foils available from the diacetylene compounds according to one of claims 1 to 4.
DE19934339646 1993-11-20 1993-11-20 New di:acetylene cpds. with extended pi-electron systems Withdrawn DE4339646A1 (en)

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Cited By (4)

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NL1009541C2 (en) * 1998-07-02 2000-01-07 Kema Nv A method of manufacturing a film of arylalkyl modified polyacetylene, the polyacetylene obtained, and the use thereof.
EP1158839A2 (en) * 2000-04-27 2001-11-28 Fujitsu Limited Organic luminous material and organic light-emitting device
EP1897886A1 (en) * 2006-09-08 2008-03-12 Bayer Schering Pharma Aktiengesellschaft Compounds as aptamer-dimers and their uses in diagnosis and therapy
JP2011099114A (en) * 2000-04-27 2011-05-19 Fujitsu Ltd Organic luminous material

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL1009541C2 (en) * 1998-07-02 2000-01-07 Kema Nv A method of manufacturing a film of arylalkyl modified polyacetylene, the polyacetylene obtained, and the use thereof.
WO2000001744A1 (en) * 1998-07-02 2000-01-13 N.V. Kema Method for manufacturing a film of arylalkyl-modified polyacetylene, said polyacetylene obtained, and the use thereof
EP1158839A2 (en) * 2000-04-27 2001-11-28 Fujitsu Limited Organic luminous material and organic light-emitting device
EP1158839A3 (en) * 2000-04-27 2006-01-11 Fujitsu Limited Organic luminous material and organic light-emitting device
EP1760799A3 (en) * 2000-04-27 2007-06-27 Fujitsu Ltd. Organic luminous material and organic light-emitting device
EP1741765A3 (en) * 2000-04-27 2007-06-27 Fujitsu Limited Organic luminous material and organic light-emitting device
EP1768466A3 (en) * 2000-04-27 2007-06-27 Fujitsu Limited Organic luminous material and organic light-emitting device
EP1768465A3 (en) * 2000-04-27 2007-06-27 Fujitsu Ltd. Organic luminous material and organic light-emitting device
KR100791527B1 (en) 2000-04-27 2008-01-04 후지쯔 가부시끼가이샤 Organic luminous material and organic light-emitting device
JP2011099114A (en) * 2000-04-27 2011-05-19 Fujitsu Ltd Organic luminous material
EP1897886A1 (en) * 2006-09-08 2008-03-12 Bayer Schering Pharma Aktiengesellschaft Compounds as aptamer-dimers and their uses in diagnosis and therapy
WO2008028530A1 (en) * 2006-09-08 2008-03-13 Bayer Schering Pharma Aktiengesellschaft Compounds as aptamer-dimers and their uses in diagnosis and therapy

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