Fluorescence spectroscopy of potential electroluminescent materials: Substituent effects on DSB and segmented PPV derivatives

Birckner, Eckhard; Grummt, U.‐W.; Rost, H.; Hartmann, Alexander K.; Pfeiffer, Steffen; Tillmann, H.; Hörhold, Hans‐Heinrich

doi:10.1007/bf02758240

Cited by 22 publications

(15 citation statements)

References 10 publications

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“…Both maxima of 6c are blue-shifted with respect to 6b. As observed by Birckner, two alkoxy substituents at the central ring blur the vibrational structure of the absorption band accompanied by the buildup of a second, less intense absorption band [28]. Furthermore, the vibronic structure of the emission band vanishes completely for the fourfold substituted DSB 6c.…”

Section: Electronic Spectramentioning

confidence: 81%

Synthesis and Electronic Spectra of Substitutedp-Distyrylbenzenes for the Use in Light-Emitting Diodes

Stalmach

Detert²

2000

J. prakt. Chem.

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Poly(p-phenylenevinylene) and its derivatives are one of the preferred groups of materials for the use as emissive layer in organic polymer light emitting diodes [1 -4]. Several groups investigated the photochemistry and particularly the photophysical behaviour of these polymers in order to establish knowledge of the fundamental properties that are responsible for the efficiencies of the devices as well as their amelioration [3 -9]. However, the fact that the parent polymer is insoluble and intractable prevents its complete characterization so that systematic investigations on structure-property relationships are almost impossible. A part of this problem can be circumvented by the investigation of model compounds. This approach, the estimation of the properties of a polymer by investigation of oligomers as model compounds is widely used, especially in the field of conjugated polymers [10 -15].Oligo(phenylenevinylene)s are useful as model compounds for the corresponding polymers and as luminescent material in Organic Light Emitting Diodes (OLEDs). Herein, the synthesis and the electronic spectra of a series of substituted distyrylbenzenes (DSBs) with a great variety of position, number, and character of substituents is reported. In order to elucidate the influence of different substitution patterns on the absorption and emission spectra, electron donors like dimethylamino and alkoxy side chains, a well as electron withdrawing groups like sulfones or nitriles and combinations of them were studied. Electron-donating ether groups have been used extensively in the field of conjugated polymers, as they reduce the band gap and allow to attach solubilising side chains. Sulfones and nitriles on the other hand, are electron withdrawing, which is especially important for a balanced charge carrier injection into the emitting material in a LED [16,17] Abstract. The influence of substitution on the absorption and Luminescence spectra of oligo(phenylenevinylene)s has been studied using distyrylbenzene (DSB) as a model compound. The degree, character, and pattern of substitution was varied systematically, altering the electronic properties of the DSB, the wavelength of the emitted light could be tuned over a for the application of metals with higher work function as cathode [18]. To allow comparison of the influences of different substitution, the basic chromophore, DSB, remains unchanged. SynthesisSeveral reactions are suitable to synthesize 1,4-distyrylbenzenes with two identical styrene units. Besides aldol-type condensations like Knoevenagel and Siegrist, Heck and Wittig-Horner reactions are most versatile. For the latter one, the starting materials are terephthaldialdehydes or 1,4-bis(halomethyl)benzenes for the central ring and benzylic halides or benzaldehydes for the lateral units.The majority of the distyrylbenzenes investigated here (6a -h) was synthesized starting with the MichaelisArbusov reaction of easily accessible 1,4-bis(chloromethyl) benzenes [19] to bisphosphonates 1a, 1b followed by PO-activated olefination ...

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Section: Electronic Spectramentioning

confidence: 81%

Synthesis and Electronic Spectra of Substitutedp-Distyrylbenzenes for the Use in Light-Emitting Diodes

Stalmach

Detert²

2000

J. prakt. Chem.

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“…This substantial challenge has stimulated commensurate efforts on the part of scientists to insulate CPs from such interactions through the incorporation of sterically encumbering side chains. [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22] These shielded materials exhibit increased solubility and solution processability, and their molecular properties more faithfully translate to the solid state. Bulky side chains can also be utilized to provide benefits such as tunable CP dielectric and porosity to analytes (i.e., for sensor applications).…”

Section: Introductionmentioning

confidence: 99%

Steric Coordination Control of Interchain Interactions in Conducting Metallopolymers

Dennis

Smith

2009

Macromol. Rapid Commun.

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The solution processability of a conducting metallopolymer (CMP1) based on a 2,2'-bipyridyl (bipy) derivatized poly(p-phenylene vinylene) (PPV) backbone has been accomplished by the strategic placement of sterically demanding mesityl side chains. The enhanced solubility of CMP1 can be traced to the prevention of coordinative crosslinking between polymer chains. The sterically enforced 1:1 bipy/metal ratio was confirmed by job analysis of absorption spectroscopic titration data. In addition to enhanced processability, this strategy also leads to twice as many metal ions, and consequently twice the charge, on CMP1 versus traditional bipyridyl-PPV metallopolymers that are typified by a 2:1 bipy/metal ratio with certain metals.

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“…16 These conjugated compounds which are accompanied by strong bathochromic shifts of the absorption and emission spectra showed increased electron affinity. 17,18 Because of their rich electronic and…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel benzothiazole compounds with an extended conjugated system

Reddy¹,

Lin²

2007

Arkivoc

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Novel cyano-substituted benzothiazoles (Schemes 1 and 2) were synthesized, which possess an extended conjugated system. Compound 6 consists of two benzothiazole units with bis(4-vinylphenyl)acrylonitrile as a bridging group and compound 12 was two benzothiazole units and two dodecyloxy bis(4-vinylphenyl)-acrylonitrile units. Absorption and fluorescence properties were studied for compounds 6 and 12.

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Fluorescence spectroscopy of potential electroluminescent materials: Substituent effects on DSB and segmented PPV derivatives

Cited by 22 publications

References 10 publications

Synthesis and Electronic Spectra of Substitutedp-Distyrylbenzenes for the Use in Light-Emitting Diodes

Synthesis and Electronic Spectra of Substitutedp-Distyrylbenzenes for the Use in Light-Emitting Diodes

Steric Coordination Control of Interchain Interactions in Conducting Metallopolymers

Synthesis of novel benzothiazole compounds with an extended conjugated system

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