Synthesis of oligomeric chains with 9,10‐dihydroanthracene units by carbanion alkylation

Bender, D.; Herbst, Heinz; Schade, P.; Müllen, Kläus

doi:10.1002/cber.19881210625

Cited by 10 publications

(3 citation statements)

References 36 publications

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“…Due to the low concentration of the initiator in the final polymerwe are not able to determine the configuration by NMR spectroscopy. However, it is known from the literature that 9,lO-disubstituted dihydroanthracenes synthesized in an anion alkylation reaction lead to a cis configuration [8].…”

Section: Resultsmentioning

confidence: 99%

Dihydroanthracene dimers as novel bifunctional initiators for anionic polymerization

1994

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Anionic polymerizations initiated with an alkylene bridged dihydroanthracene dimer as a bifunctional initiator are described as a synthetic route to polymers containing the dianthryl species in the center of the macromolecular chain. The approach taken herein involves the twofold deprotonation of 1,3-di- (9,9 'J0,lO '-tetrahydro-9,9 '-anthry1)propane and the initiation of methyl methacrylate polymerization at both anionic sites.The synthesis ofABA block copolymers by addition of tert-butyl acrylate as a second monomer is described. Polymer analogous aromatization of the initiator generates the corresponding polymer with two anthracene units in the main chain. The synthezised homo-and block copolymers have been fully characterized by GPC, UV and NMR measurements.

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Section: Resultsmentioning

confidence: 99%

Dihydroanthracene dimers as novel bifunctional initiators for anionic polymerization

1994

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“…'H NMR (400 MHz,CDCI,): 6,= 8,[5][6][7]4,5,8,9,anthracene unit);7,3,6,7,anthracene unit); 4,O-3,5 (H-ll,l2; bridging group; H-9,10, dihydroanthracene unit); 2,s -1 , O (H-12, bridging group). The mixture was allowed to cool to room temperature, and the resulting dark-brown glassy product was powdered.…”

Section: Experimental Partmentioning

confidence: 99%

“…l3C NMR (100 MHz, CDCI,) (THF-soluble fraction): 6, = 140,2 (C-4a,8a,9a,lOa, dihydroanthracenegroup); 135,0,133,7,132,1,130,1,130,0,129,8a,9a,lOa,9,10,anthracenegroup);128,1,127,1,126,1,125,9,125,5,125,3,125,2,124,anthracene and dihydroanthracene group);33,1,28,4,28,l2,bridging group Reduction of poly(9,10-anthrylenefrimethylene) (3 a) with lithium: The reduction was performed in a special glass ampoule consisting of two 100-ml compartments connected by a constriction in the glass. Compound 3 a (300 mg, THF-soluble fraction, a, = 1 600) was placed in one compartment, and the ampoule connected with the vacuum line.…”

Section: Experimental Partmentioning

confidence: 99%

Reductive transformations, 12. Poly(9,10‐anthrylenetrimethylene) as an efficient electron acceptor

Bender¹,

Przybylski²,

Müllen³

1989

Makromol. Chem.

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Poly(9,lO-dihydroanthrylenetrimethylene) (2) comprises a novel chain-type structure in which 9,lO-dihydroanthracene units are linked by flexible spacer groups. Upon dehydrogenation with sulfur at elevated temperature, polymer 2 is converted into the corresponding polyanthrylene system 3. NMR-and UV-spectroscopic data provide firm evidence for the dehydrogenation process. The polymer 3 was subjected to reduction with active lithium, and the resulting polyanions were characterized by NMR spectroscopy and by quenching experiments. It appears that each anthracene unit of the chain can be charged with two electrons.

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Novel Alkylanthracenes Synthesis, Reductive Alkylation, and Reductive Polymerization

Bender

Müllen

1988

Chem. Ber.

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A series of novel substituted anthracenes has been prepared which carry two or'four n-alkyl groups at C-2 and C-3 (C-6 and C-7). The route taken includes the synthesis of novel 2,3-dialkylbutadienes, their Diels-Alder reaction with l&benzo-or l&naph-thoquinone, the dehydrogenation of the adducts, and the reduction of the anthraquinones. The substituted anthracenes are submitted to reduction and reductive alkylation in ethereal solvents and in liquid ammonia to yield 9,10-dialkyl-substituted 9,10-dihydroanthracenes. A modification of the reductive alkylation, i.e. the introduction of 1 ,ndihaloalkanes as electrophiles, provides polymeric chains, in which dihydroanthracene moieties are linked by alkanediyl bridges. It appears that the behavior of alkyl-substituted anthracenes in reductive alkylation and reductive polymerization reactions is completely different to that of the parent anthracene. This feature, which follows from different solubilities and basicities of carbanionic intermediates in the solvent systems, allows to control the properties of the polymer chains.

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Synthesis of oligomeric chains with 9,10‐dihydroanthracene units by carbanion alkylation

Cited by 10 publications

References 36 publications

Dihydroanthracene dimers as novel bifunctional initiators for anionic polymerization

Dihydroanthracene dimers as novel bifunctional initiators for anionic polymerization

Reductive transformations, 12. Poly(9,10‐anthrylenetrimethylene) as an efficient electron acceptor

Novel Alkylanthracenes Synthesis, Reductive Alkylation, and Reductive Polymerization

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