Packing Modes of Distyrylbenzene Derivatives

Bartholomew, Glenn P.; Bazan, Guillermo C.; Bu, Xianhui; Lachicotte, Rene J.

doi:10.1021/cm991194o

Cited by 51 publications

(58 citation statements)

References 26 publications

(40 reference statements)

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“…The crystal structures of various OPV derivatives have been extensively investigated previously 17. 18 It is well understood that the crystals of unsubstituted OPV molecules consist of stacks of basal planes with herringbone intraplane packing, and the strongest interactions exist between the nearest edge‐to‐face neighbors within the plane, which give so‐called H‐aggregates 17. Figure 2 b shows a direct view of the arrangement of fluorescent chromophores in the TOPV crystal.…”

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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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 particular, such an example was reported very recently for αDCS (i.e., with CN substitution in the inner vinylene position). Here, while the molecules in the blue‐emitting phase are strongly twisted, those in the green‐emitting phase are almost planar; conversion between the two phases can be achieved through pressure application. This is considered to be important for practical application of the twist elasticity concept, proving that strong changes in molecular twists are not only driven by additional substituents but also can be operative by slight changes in the crystal growth conditions of one and the same material.…”

Section: Introductionmentioning

confidence: 99%

Twist‐Elasticity‐Controlled Crystal Emission in Highly Luminescent Polymorphs of Cyano‐Substituted Distyrylbenzene (βDCS)

Shi

Yoon

Viani

et al. 2017

Advanced Optical Materials

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The occurrence of polymorphs in crystals of luminescent π‐conjugated organic materials is an intriguing matter, particularly because polymorphs can give rise to widely different broadband and amplified emission properties. Here, a new, highly luminescent polymorph of cyano‐substituted distyrylbenzene, being a prominent example of “twist elasticity”—the ability of a molecule to react to external constraints with substantial changes in the torsional coordinates, is investigated. The twist elasticity concept is fully explored here through molecular modeling by comparison of the new polymorph with two known ones exhibiting largely different intra‐ and intermolecular coordinates. In a second step, the impact of intra‐ and intermolecular contributions on the spontaneous and stimulated emission properties observed in the crystals is rationalized, being in all a crucial step in targeted design of optoelectronic materials.

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“…Epstein et al described poly( p -pyridine)- and poly( p -pyridyl vinylene)-based polymers as emissive layers in light-emitting devices [12]. Bartholomew et al [13] studied model compounds, such as phenylated PPV, also with the electron withdrawing cyano group attached to the olefin, and they can also be used as a model cyano substitute (CN-PPV).…”

Section: Introductionmentioning

confidence: 99%

Theoretical and Experimental Spectroscopic Analysis of Cyano-Substituted Styrylpyridine Compounds

Castro

Percino

Chapela

et al. 2013

IJMS

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A combined theoretical and experimental study on the structure, infrared, UV-Vis and 1H NMR data of trans-2-(m-cyanostyryl)pyridine, trans-2-[3-methyl-(m-cyanostyryl)] pyridine and trans-4-(m-cyanostyryl)pyridine is presented. The synthesis was carried out with an efficient Knoevenagel condensation using green chemistry conditions. Theoretical geometry optimizations and their IR spectra were carried out using the Density Functional Theory (DFT) in both gas and solution phases. For theoretical UV-Vis and 1H NMR spectra, the Time-Dependent DFT (TD-DFT) and the Gauge-Including Atomic Orbital (GIAO) methods were used, respectively. The theoretical characterization matched the experimental measurements, showing a good correlation. The effect of cyano- and methyl-substituents, as well as of the N-atom position in the pyridine ring on the UV-Vis, IR and NMR spectra, was evaluated. The UV-Vis results showed no significant effect due to electron-withdrawing cyano- and electron-donating methyl-substituents. The N-atom position, however, caused a slight change in the maximum absorption wavelengths. The IR normal modes were assigned for the cyano- and methyl-groups. 1H NMR spectra showed the typical doublet signals due to protons in the trans position of a double bond. The theoretical characterization was visibly useful to assign accurately the signals in IR and 1H NMR spectra, as well as to identify the most probable conformation that could be present in the formation of the styrylpyridine-like compounds.

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Packing Modes of Distyrylbenzene Derivatives

Cited by 51 publications

References 26 publications

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

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

Twist‐Elasticity‐Controlled Crystal Emission in Highly Luminescent Polymorphs of Cyano‐Substituted Distyrylbenzene (βDCS)

Theoretical and Experimental Spectroscopic Analysis of Cyano-Substituted Styrylpyridine Compounds

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