Synthesis and electronic spectra of substituted oligo(phenylenevinylene)s

Detert, Heiner; Sugiono, Erli

doi:10.1002/1099-1395(200010)13:10<587::aid-poc275>3.0.co;2-i

Cited by 13 publications

(3 citation statements)

References 19 publications

(11 reference statements)

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“…Other methods that are used successfully in this work include McMurry 24 and Knoevenagel , reaction procedures. Again, thioesters would have been absolutely intolerable, whereas these methods proved fully compatible with t -Bu sulfide protection.…”

Section: Introductionmentioning

confidence: 99%

Novel Synthesis of Protected Thiol End-Capped Stilbenes and Oligo(phenylenevinylene)s (OPVs)

et al. 2003

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The first general procedures for preparation of thiol end-capped stilbenes and oligo(phenylenevinylene)s (OPVs) with tert-butyl- and acetyl-protected thiol termini have been developed. These reactions proceed via Br/Li exchange, McMurry, and Wittig-type reactions. The thiol functionality is protected against strong basic and acidic reaction conditions as a t-Bu sulfide. As a key point in the method, reprotection of the thiol group is accomplished by means of acetyl chloride and boron tribromide. The novel strategy forms the basis for stepwise introduction of 4-mercaptostyryl units in OPVs. The new mono-, di-, and trimercapto OPVs have potential applications as one, two, and three terminal molecular devices in gold nanoparticle clusters, self-assembled monolayers, and optoelectronic devices.

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Section: Introductionmentioning

confidence: 99%

Novel Synthesis of Protected Thiol End-Capped Stilbenes and Oligo(phenylenevinylene)s (OPVs)

et al. 2003

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“…21 All spectra and the melting point were as reported. 22 The bromomethylation of 6 using a method similar to that reported 23,24 carried out in acid-washed glassware using paraformaldehyde and KBr in acetic acid produced di-noctyloxy-1,4-bis(bromomethyl)benzene (7) in 73% yield. The Arbuzov reaction yielded 2,5-di-n-octyloxy-1,4-xylenediethylphosphonate ester (8) in a 71% yield.…”

Section: Resultsmentioning

confidence: 95%

Systematic Study of the Effects of Naphthalene and Anthracene Substitution on the Properties of PPV Derivative Conjugated Systems

Lynch¹,

O’Neill²,

Bradley³

et al. 2007

Macromolecules

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The systematic synthesis of poly(phenylvinylene) (PPV) derivatives by the Wittig-Horner reaction is reported. The phenyl units of the PPV structure are methodically substituted by naphthyl and anthryl units to form a homologous series of structures. The 2,6 attachment of the vinylene linkage on the anthryl ring provides novel structures that have not been reported before due to their synthetic inaccessibility. The introduction of naphthyl units results in a hypsochromatic shift in the absorption and emission spectra, while the introduction of anthryl units leads to a bathochromatic shift relative to the naphthalene structures. The observed structural variation of the spectroscopic properties is explained in terms of a combination of the increased conjugation of the substituent acene units and the decreased electronic contribution across the vinyl linkage.

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“…The fluorescence quantum yields in cyclohexane being 0.3 -0.4 (1, 2) and 0.6 -0.7 (3, 4) respectively decrease along with increasing polarity to values around 0.05 -0.1 in acetonitrile. Generally, phenylenevinylene chromophores are fairly stable towards light or acid, but UV-irradiation of slightly acidic solutions initiates a fast and irreversible decomposition of these materials [19]. Chromophores with basic sites like 1 -4 show a much higher photostability, even in very acidic solutions.…”

Section: Electronic Spectramentioning

confidence: 99%

Proton-Induced Multiple Changes of the Absorption and Fluorescence Spectra of Amino-Aza-Oligo(Phenylenevinylene)s

Schmitt¹,

Glang²,

Preis³

et al. 2008

Advances in Science and Technology

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Fluorescent dyes with a high sensitivity of their optical spectra towards changes of the environment were prepared via aldol condensation or Horner olefinations. The main chromophore is a quadrupolar N-substituted 1,4-distyrylbenzene which allows protonation and complexation at various positions resulting in a series of different and significant changes of the optical spectra. The sensitivity of the absorption and emission spectra on solvent polarity, acid, and cations is reported.

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Synthesis and electronic spectra of substituted oligo(phenylenevinylene)s

Cited by 13 publications

References 19 publications

Novel Synthesis of Protected Thiol End-Capped Stilbenes and Oligo(phenylenevinylene)s (OPVs)

Novel Synthesis of Protected Thiol End-Capped Stilbenes and Oligo(phenylenevinylene)s (OPVs)

Systematic Study of the Effects of Naphthalene and Anthracene Substitution on the Properties of PPV Derivative Conjugated Systems

Proton-Induced Multiple Changes of the Absorption and Fluorescence Spectra of Amino-Aza-Oligo(Phenylenevinylene)s

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