The preparations and some properties of mixed aryl-thienyl oligomers and polymers

Pelter, Andrew; Jenkins, Ieuan H.; Jones, David

doi:10.1016/s0040-4020(97)00629-7

Cited by 69 publications

(57 citation statements)

References 95 publications

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“…[9] Concerning the access to 2, the protocol proposed herein is an efficient alternative to the reaction of thiophene in the presence of a catalytic amount of concentrated sulfuric acid with a cis/trans mixture of 3,6-dimethoxy-3,6-dimethylcyclohexa-1,4-diene (ca. 1:1), itself obtained by electrochemical oxidation of p-xylene.…”

Section: Synthesismentioning

confidence: 99%

“…[10] Moreover, the preparative method described herein was very convenient for the preparation of the three-ring compounds 4-6 and avoided the elaboration of specific reactive species such as 2-thienylbis-(isobutyloxy)borane to prepare 4 in 72 % yield in a 24 h Suzuki coupling or 2-thienylcadmium chloride, prepared from toxic but more easily dried and stored cadmium chloride, to obtain 5 in 57 % yield. [9] Finally, 6 was selectively prepared according to Scheme 1, whereas use of 2-thienylzinc chloride in a palladium(0)-catalysed cross-coupling with 1,4-dimethoxybenzene yielded a five-ring byproduct (14 %) besides the desired three-ring oligomer synthesised in 49 % yield. [9] To prepare 7, 2,5-dimethoxyphenol [11] was O-alkylated in 93 % yield with one equivalent of benzyl bromide in the presence of K 2 CO 3 in refluxing acetonitrile (Scheme 2).…”

Section: Synthesismentioning

confidence: 99%

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How to Build Fully π‐Conjugated Architectures with Thienylene and Phenylene Fragments

et al. 2007

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A series of small-sized model π-conjugated oligomers have been prepared from thienylene and phenylene or dimethylor dimethoxy-substituted phenylene units. Crystallographic data for the methoxylated compound show a quasi-planar conformation with a non-covalent S-O interaction. The resulting strong conjugation in the gas phase has also been highlighted by UV/photoelectron spectroscopy and theoretical calculations (DFT). Indeed, for these compounds there is a large energy gap ∆E π arising from the interaction between the molecular orbitals of the isolated thienylene-phenylene species. This can be explained in terms of the energies of the two π orbitals of the dimethoxyphenylene unit, the shape of these molecular orbitals in a three-orbital interaction diagram and by the presence of the S···O interaction which re-

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Section: Synthesismentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

How to Build Fully π‐Conjugated Architectures with Thienylene and Phenylene Fragments

et al. 2007

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“…Different carbo-and heterocyclic systems have been used to replace the phenylene moiety in PPV [119]. In Figs.…”

Section: Modification Of Electronic Properties Of Conjugated Polymersmentioning

confidence: 99%

The chemistry of electroluminescent organic materials

Segura¹

1998

Acta Polym.

287

200

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Electroluminescence has been a subject of interest for several decades because of its many applications in areas such as telecommunications or information displays. Light‐emitting diodes using p‐n junctions of inorganic semiconductors have dominated the field in the last twenty years; however, efficient blue emission has only recently been achieved and inorganic semiconductors are difficult to form over large areas, making the process uneconomic. During the last decade, an explosive growth of activity in the area of organic electroluminescence has occurred in both academia and industry, stimulated by the promise of light‐emitting plastics for the fabrication of large, flexible, inexpensive and efficient screens to be used in different applications. Thus, a substantial amount of research is presently directed towards color control and improvement of manufacturability and reliability of devices in order to make their commercialization viable. A great deal of work has been carried out by physicists and materials scientists concerned with the preparation of different device structures and with the use of different techniques for device manufacture. However, all this work would not be possible without the continuous efforts of synthetic chemists to prepare materials with enhanced luminescent properties and processabilities. This article provides a review of the main types of organic materials that have been used in the fabrica‐tion of light‐emitting diodes either as emitting materials or as charge‐transport layers. Special attention will be paid to the different synthetic strategies that have been followed in order to tune the color of the emission, to increase stability of materials and to enhance their processabilities.

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“…Treatment of 5 with copper cyanide in dimethylformamide [30] led to the dicyano derivative 6, which upon reduction with DIBAL-H yielded dialdehyde 7. Reduction with sodium tetrahydroborate and treatment with boron trifluorideϪdiethyl ether and tetraethylammonium bromide in dichloromethane [31] afforded the dibromomethyl derivative 9 which was finally treated with triphenylphosphane (in refluxing DMF) to give the corresponding 1,5-dihexyloxy-2,6-bis[(triphenylphosphonio)methyl]naphthalene dibromide (10). Alternatively, solidstate reaction of 9 with potassium cyanide and aliquat [32] yielded 2,6-bis(cyanomethyl)-1,5-dihexyloxynaphthalene (11).…”

Section: Resultsmentioning

confidence: 99%

“…PPV, [1,2,10] the development of new fluorophores to be used Apart from being very resistant organic materials, PPP deas building blocks for the preparation of either conjugated rivatives are very interesting because they offer the possibilor non-conjugated materials having gained great attention. ity of tuning the color of the emission by the production of A common feature of conjugated polymers is that they derivatives with different torsion angles between consecuinevitably contain randomly distributed defects, i.e., nontive rings.…”

Section: Introductionmentioning

confidence: 99%

Oligo-2,6-naphthylenevinylenes – New Building Blocks for the Preparation of Photoluminescent Polymeric Materials

1999

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Synthetic strategies towards appropriate symmetric and unsymmetric functionalization of the naphthalene ring are presented. By means of Knoevenagel and Wittig condensation reactions new fluorescent, differently functionalized oligo(2,6‐naphthylenevinylene)s have been synthesized, the presence of terminal aldehyde or bromine substitution opening the way to the incorporation of the fluorescent trimers in a variety of polymeric materials. The effect of substituting the phenylene ring by the more bulky dialkoxynaphthalene system in arylenevinylene‐type materials is studied from the structural point of view and the possibility to tune the emission color and the electron affinity through the introduction of naphthylenevinylene and cyano‐substituted naphthylenevinylene units is also investigated.

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The preparations and some properties of mixed aryl-thienyl oligomers and polymers

Cited by 69 publications

References 95 publications

How to Build Fully π‐Conjugated Architectures with Thienylene and Phenylene Fragments

How to Build Fully π‐Conjugated Architectures with Thienylene and Phenylene Fragments

The chemistry of electroluminescent organic materials

Oligo-2,6-naphthylenevinylenes – New Building Blocks for the Preparation of Photoluminescent Polymeric Materials

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