Synthesis, crystal structure determination and photoluminescence properties of a pure anti trans-trans phenylenevinylene derivative

Cárdenas, Juan C.; Ochoa‐Puentes, Cristian; Gutiérrez‐Puebla, Enrique; Sierra, César A.

doi:10.1016/j.synthmet.2016.02.021

Cited by 8 publications

(5 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In addition, EW substituents have a greater bathochromic effect than ED substituents. This observation is in agreement with our previous results , …”

Section: Resultssupporting

confidence: 94%

Pd/Halloysite as a Novel, Efficient and Reusable Heterogeneous Nanocatalyst for the Synthesis of p‐Phenylenevinylene Oligomers

et al. 2018

Self Cite

View full text Add to dashboard Cite

The potential applications of poly(p‐phenylene vinylene) derivatives and its oligomers in organic electronics have attracted great interest in recent years. In this study, a novel palladium supported on halloysite heterogeneous catalyst (Pd/HNTs) was prepared, characterized and its catalytic activity for obtaining p‐phenylenevinylene oligomers was investigated in the Heck coupling of styrene and 2,5‐diiodo‐1,4‐dimethoxybenzene using conventional and environmentally benign solvents. Thus, in the presence of 0.75 mol% catalyst, the product was obtained in 76% yield using ethanol as solvent. To evaluate the versatility of the Pd/HNTs catalyst, the synthesis of a series of p‐phenylenevinylene oligomers and divinylbenzene derivatives was performed obtaining yields between 58 and 93%. In addition, the catalyst could be recovered and reused for four reaction cycles without significant loss of its catalytic activity. Finally, the photophysical characterization of the synthesized molecules was performed.

show abstract

“…In addition, EW substituents have a greater bathochromic effect than ED substituents. This observation is in agreement with our previous results , …”

Section: Resultssupporting

confidence: 94%

Pd/Halloysite as a Novel, Efficient and Reusable Heterogeneous Nanocatalyst for the Synthesis of p‐Phenylenevinylene Oligomers

et al. 2018

Self Cite

View full text Add to dashboard Cite

show abstract

“…Therefore, the synthesis of 1 was performed using a previously optimized solvothermal Heck reaction, which produces the compound with the desired stereoselectivity in good yield (Scheme 1). 32 The catalytic system offered by Pd(dba) 2 and P(OPh) 3 has been found to be ideal for obtaining PV systems with 21/2 electronic conjugation length and trans−trans configuration, selectively. This high selectivity can be attributed to the steric hindrance and electronic properties of the phosphite ligand, which results in an enhanced orientation control of the substrates during the C−C coupling step and also in an improvement of the catalytic cycle kinetics.…”

Section: Resultsmentioning

confidence: 99%

Nature of Color Diversity in Phenylenevinylene-Based Polymorphs

Cárdenas

Aguirre-Díaz

Galindo

et al. 2019

Crystal Growth & Design

Self Cite

View full text Add to dashboard Cite

In this work we present a joint experimental and theoretical study of the light emitting properties of (E,E)-2,5-dimethoxy-1,4-bis[2-(4-carboxylatestyryl)]benzene, a phenylenevinylene (PV, from now on) derivative in the solid state. Careful crystal growth under different conditions of this PV luminophore yields three different crystals with dissimilar color emissions with maxima ranging between 504 and 565 nm. Single crystal structure elucidations indicate that they correspond to a DMF solvate, denoted 2·DMF (yellow) and two conformational polymorphs named 2α (yellow) and 2β (orange). Analysis of the close contacts and the framework topologies help us to rationalize the different colors observed, not only on the basis of different intramolecular conformations but also of the different intermolecular interactions observed. Particularly, the presence of different C–H···π and π···π interactions in 2α and in 2β polymorphs, respectively, give rise to different supramolecular frameworks with hex and bcu topologies. Theoretical studies reinforce the hypothesis that cooperative π···π interactions in the crystal lattice are responsible for the red-shifted color observed in the polymorph 2β. In fact, in contrast to what is observed with the polymorph 2α, as we incorporate more monomers in the calculations of the optical properties of polymorph 2β, the estimated energy for the vertical excitation from the ground state to the first excited state moves to lower values.

show abstract

“…The computational cost of working with oligomers is much more reachable than that for working with polymers. Furthermore, in the electronically conjugated polymers, the segmented part and its properties can be easily modelled in computer and these data can be validated by the experimental results obtained with the previously synthesized structurally analogous oligomers, which can often include even the crystal structure (Figure 3) [30]. In applications like OLEDs, the optical and electrical behavior comes from the polymer in solid state; unfortunately, getting the solid-state structure of a polymer is not an easy task.…”

Section: The Oligomer Approachmentioning

confidence: 98%

Phenylenevinylene Systems: The Oligomer Approach

Cárdenas¹,

Ochoa‐Puentes²,

Sierra³

2016

Conducting Polymers

Self Cite

View full text Add to dashboard Cite

Among conducting polymers, poly-p-phenylenevinylenes (PPVs) have attained a special place in polymer electronics. The optoelectronic properties initially exposed by PPVs in organic light-emitting diodes (OLEDs) turned these organic electronic conjugated systems from the solo academic interest into a technologically very promising area. The easiness of the tuning of their optoelectronic properties through synthetic modifications make PPVs an outstanding and suitable compound for technological applications and fundamental science development. Unfortunately, the synthesis and structural optoelectronic characterization of novel PPVs is a long and difficult task that sometimes yields unclear results. However, phenylenevinylene oligomers (oPV) can be synthesized and characterized in a very straightforward manner, and their performance in novel applications can be directly related to their structural analogue polymer, methodology designated as the oligomer approach. Herein, we describe the oligomer approach using the Mizoroki-Heck reaction as a synthetic route for oPVs and PPVs, and the importance of an extensive characterization for novel applications, such as photocatalysis and matrix-assisted laser desorption/ionization (MALDI) matrices, where these electronic conjugated systems have very promising applications.

show abstract

Synthesis, crystal structure determination and photoluminescence properties of a pure anti trans-trans phenylenevinylene derivative

Cited by 8 publications

References 42 publications

Pd/Halloysite as a Novel, Efficient and Reusable Heterogeneous Nanocatalyst for the Synthesis of p‐Phenylenevinylene Oligomers

Pd/Halloysite as a Novel, Efficient and Reusable Heterogeneous Nanocatalyst for the Synthesis of p‐Phenylenevinylene Oligomers

Nature of Color Diversity in Phenylenevinylene-Based Polymorphs

Phenylenevinylene Systems: The Oligomer Approach

Contact Info

Product

Resources

About