(<i>E</i>,<i>E</i>)-2,5-Dipropoxy-1,4-bis[2-(2,4,6-trimethoxyphenyl)ethenyl]benzene

Velde, Christophe M. L. Vande; Baeke, Jan K.; Geise, H. J.; Blockhuys, Frank

doi:10.1107/s0108270105007778

Cited by 12 publications

(14 citation statements)

References 5 publications

(7 reference statements)

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“…The choice of the [sp,sp] conformer is based on recent structural studies performed on compounds 4a, 4c, 4f, 4i, 4l, 5a and 7 which showed that this is the conformer also found in the crystal [13,[16][17][18]. Calculated geometries of the neutral forms of compounds 4a, 4b, 4c, 4h, 4k, 4l, 5a and 7 present no surprises.…”

Section: Theoretical Calculationsmentioning

confidence: 93%

The electrochemistry of alkoxylated arylene vinylene oligomers: Oxidation potentials and diffusion coefficients

Baeke

Nowaczyk

Moens

et al. 2007

Journal of Electroanalytical Chemistry

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Section: Theoretical Calculationsmentioning

confidence: 93%

The electrochemistry of alkoxylated arylene vinylene oligomers: Oxidation potentials and diffusion coefficients

Baeke

Nowaczyk

Moens

et al. 2007

Journal of Electroanalytical Chemistry

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“…The parallel molecular packing is mainly attributed to the steric hindrance introduced by the thiomethyl and methoxyl units. The existence of strong OCH 3 ⋅⋅⋅ π interaction19 is evident from the close contact (2.682 Å) between the terminal hydrogen atom on the methoxyl group and the center of the middle ring in the neighboring molecule.…”

Section: Methodsmentioning

confidence: 99%

Strong Two‐Photon Excited Fluorescence and Stimulated Emission from an Organic Single Crystal of an Oligo(Phenylene Vinylene)

et al. 2010

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In this Communication Figure 5 and Figure S5 in the Supporting Information were misinterpreted as a result of an experimental artifact. While we wrote on page 734, that two-photon excited fluorescence of TOPV in the solid state can be unambiguously recorded even on a standard spectrofluorimeter with a Xe lamp as excitation source, a critical reader noticed that a high-intensity laser is still needed to promote a material in the excited state by a two-photon absorption process. In additional experiments we found that the observed emission applying an excitation at 800 nm was a result of the higher order of the diffraction light in the monochromator of the spectrofluorimeter used. Thus, there are also photons available at 400 nm for one-photon excitation, although 800 nm was set as the excitation in the equipment. Diffraction light of a higher order in the monochromator caused the observed emission. This mistake happened as a result of relying on the specifications of the commercial equipment used for the experiments, which suggests that higher-order diffraction light from the monochro-mator is completely filtered out. This assumption led us to draw an incorrect conclusion because we believed our material has such a strong two-photon absorption that just a Xe lamp could be sufficient to promote the material by a two-photon absorption process. As the content that refers to Figure 5 and Figure S5 is based on a wrong assumption this part of the article is incorrect. A high-intensity laser source is still needed for two-photon excitation, as described elsewhere. [1] Soon after the publication of our Communication, we noticed a new article by Spano [2] which revealed that some organic dyes that were formerly thought to form J-aggregates based on spectral shifts are actually H-like aggregates. Further investigation suggested that the TOPV molecules may exhibit similar behavior. Although comparison between the molecular and powder absorption (Figure S3 in the Supporting Information) suggests a red-shift of the absorption in the solid state versus in solution, TOPV molecules might form weakly coupled H-aggregate rather than J-aggregate as we had ascribed in our Communication. The small bump at 467 nm in the powder emission spectrum (Figure S3 in the Supporting Information) become apparent in nanoparticles with increasing molecular disorder, and therefore can be assigned to the 0-0 band of H-aggregates. [2,3] The table of contents entry may also confuse some readers. The meaning of "Low in, high out" used in the Communication refers to the nature of TPA phenomenon. The TOPV molecule emits one higher-energy photon after absorbing two low-energy photons. No quantitative two-photon absorptivity of the crystal is meant in this context.

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“…The solid-state structures and electronic properties of one particular class of these oligomeric organic semiconductors, viz. distyrylbenzenes, oligomeric derivatives of PPV [poly(pphenylene vinylene)], have already been extensively studied and the influence of substituents on the properties of the carbon backbone have been investigated (Baeke et al, 2007;Vande Velde et al, 2004;Vande Velde, Baeke et al 2005;Vande Velde, De Borger et al, 2005;Vande Velde et al, 2006;Irngartinger et al, 1994;Hakansson et al, 1992;Bartholomew et al, 2000a,b;Coates et al, 1998;Nohra et al, 2006;Renak et al, 1999;Sancho-Garcia et al, 2005;Zeller et al, 2005). However, keeping in mind the tunability of these materials, it is equally interesting to determine the effects of the replacement of the ethenylic -CH CH-link by other spacers such as -CH N-…”

Section: Commentmentioning

confidence: 99%

Synthesis and structures of substituted triphenyl(phenylimino)phosphoranes

et al. 2009

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Three substituted triphenyl(phenylimino)phosphoranes, namely (4-cyanophenylimino)triphenylphosphorane, C(25)H(19)N(2)P, (I), (4-nitrophenylimino)triphenylphosphorane, C(24)H(19)N(2)O(2)P, (II), and (3-nitrophenylimino)triphenylphosphorane, C(24)H(19)N(2)O(2)P, (III), were synthesized as precursors for the preparation of substituted diphenylcarbodiimides. All three compounds display a supramolecular arrangement in which the substituted benzene rings are organized in an antiparallel fashion. The nitro group on the ring participates in C-H...O and O...pi interactions, forming intermolecular dimers. Compound (III) shows disorder which involves the rotation of one of the phenyl rings of the triphenylphosphine group.

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(E,E)-2,5-Dipropoxy-1,4-bis[2-(2,4,6-trimethoxyphenyl)ethenyl]benzene

Cited by 12 publications

References 5 publications

The electrochemistry of alkoxylated arylene vinylene oligomers: Oxidation potentials and diffusion coefficients

The electrochemistry of alkoxylated arylene vinylene oligomers: Oxidation potentials and diffusion coefficients

Strong Two‐Photon Excited Fluorescence and Stimulated Emission from an Organic Single Crystal of an Oligo(Phenylene Vinylene)

Synthesis and structures of substituted triphenyl(phenylimino)phosphoranes

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