A Novel Series of Copolymers Containing 2,5-Dicyano-1,4-phenylenevinylene-Synthetic Tuning of the HOMO and LUMO Energy Levels of Conjugated Polymers

Xiao, Yang; Yu, Wenbo; Chua, Soo-Jin; Huang, Wei

doi:10.1002/(sici)1521-3765(20000417)6:8<1318::aid-chem1318>3.0.co;2-i

Cited by 30 publications

(9 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It was demonstrated that the introduction onto the PPV skeleton of units with different electron affinity, such as alkoxy electron-donating and cyano electron-withdrawing groups, can be used as a valuable strategy to modify and adjust the HOMO and LUMO energy levels of the materials, obtaining a better matching with the work function of metal electrodes in OLED devices, thus improving performances [56,57]. In this contest, fluorine atoms appeared very interesting as for electron-withdrawing functionalities.…”

Section: Resultsmentioning

confidence: 99%

Synthetic Aspects and Electro-Optical Properties of Fluorinated Arylenevinylenes for Luminescence and Photovoltaics

et al. 2013

View full text Add to dashboard Cite

In this review, the main synthetic aspects and properties of fluorinated arylenevinylene compounds, both oligomers and polymers, are summarized and analyzed. Starting from vinyl organotin derivatives and aryl halides, the Stille cross-coupling reaction has been successfully applied as a versatile synthetic protocol to prepare a wide series of π-conjugated compounds, selectively fluorinated on the aromatic and/or vinylene units. The impact of fluoro-functionalization on properties, the solid state organization and intermolecular interactions of the synthesized compounds are discussed, also in comparison with the non-fluorinated counterparts. Luminescent and photovoltaic applications are also discussed, highlighting the role of fluorine on the performance of devices.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthetic Aspects and Electro-Optical Properties of Fluorinated Arylenevinylenes for Luminescence and Photovoltaics

et al. 2013

View full text Add to dashboard Cite

show abstract

“…The following starting materials were prepared according to literature methods: 1,4-diiodo-2,5-dihexylbenzene 37 and 2,5-dicyano-1,4-bis(bromomethyl)benzene. 38 4-Butyl-N,N-diphenyl-aniline (1). To a solution of tris-(dibenzylideneacetone)dipalladium (Pd 2 dba 3 ) (1.099 g, 1.2 mmol) and bis(diphenylphosphino)ferrocene (dppf) (0.998 g, 1.8 mmol) in toluene (180 mL) under nitrogen atmosphere was added bromobenzene (28.264 g, 180 mmol) and the resultant solution was stirred for 10 min at ambient temperature.…”

Section: Methodsmentioning

confidence: 99%

Five Orders-of-Magnitude Enhancement of Two-Photon Absorption for Dyes on Silver Nanoparticle Fractal Clusters

et al. 2002

View full text Add to dashboard Cite

Strong enhancement of the two-photon absorption of organic molecules near silver nanoparticle fractal clusters has been observed and has been exploited to yield composite materials with very strong two-photon absorption and two-photon-excited fluorescence properties. Measurements on cluster films coated with chromophoric polymer or with thiol-bound chromophores give spatially-averaged enhancements of 1000 and 20 000, respectively. Two-photon fluorescence microscopy studies show that the enhancements are spatially inhomogeneous, with peak-enhancement factors of g 10 000 (polymer/cluster) and g 160 000 (thiol chromophore/cluster), and excitation frequency dependent. These results are in accord with theoretical predictions of local-field effects due to strong localization of collective plasmon modes in fractal metal clusters, and demonstrate an approach to ultrasensitive two-photon processes.

show abstract

“…Because most conjugated polymers such as PPV are better suited for hole injection and transport compared with electron injection and transport, the unsatisfactory quantum efficiency of OLEDs is attributed to the lower injection rate of electrons from the cathode into the polymer emissive layer. On the basis of the p-n diblock concept, Huang et al synthesized a conjugated polymer consisting of 2,2′-bipyridylenevinylene (BPyV) and 2-meth-oxy-5- The polymer can be changed from a typical hole-transport (HT) material to a typical electron-transport (ET) material by varying the monomer feed ratio [24]. Quantum chemical calculations and previous research have demonstrated that introducing an electron-withdrawing group onto either the aryl ring or the vinyl group of PPV can lower both the HOMO and LUMO energy levels of the polymer, thus improving electron injection.…”

Section: Synthesizing Linear P-n Diblock Polymers To Adjust the Energmentioning

confidence: 99%

Effective adjustment of the optoelectronic properties of organic conjugated materials by synthesizing p-n diblock molecules

Jiang

2011

Chin. Sci. Bull.

View full text Add to dashboard Cite

Because organic conjugated materials offer several advantages relative to their inorganic counterparts, the development of organic conjugated materials has been one of the most active research areas in optoelectronic materials. For almost two decades, the search for organic conjugated materials has represented a major driving force for research concerned with controlling the band gap of extended π-conjugated molecules. In particular, among the parameters affecting the performance of organic light-emitting diodes (OLEDs), the energy levels of organic conjugated materials play an important role because they can affect the driving voltage, wavelength, efficiency, and lifetime of the final device. Balanced injection and transport of electrons and holes are therefore crucial for achieving OLEDs with high quantum efficiency. In this regard, research into adjusting the energy levels of organic conjugated materials is very meaningful for the development of OLEDs. To adjust the energy levels of the organic conjugated materials, Huang et al. have presented a new molecular design and synthesis route that yields p-n diblock conjugated copolymers and oligomers. The present review summarizes and analyzes the progress on adjusting the optoelectronic properties of organic conjugated materials that is due to synthesizing p-n diblock molecules. We discusses primarily work done by Huang et al., but also discusses work done elsewhere over the past few years. We also point out issues that require attention, and highlight hot spots that require further investigation.adjust, diblock, energy levels, organic light-emitting diodes, synthesize Citation:Jiang H J. Effective adjustment of the optoelectronic properties of organic conjugated materials by synthesizing p-n diblock molecules.

show abstract

A Novel Series of Copolymers Containing 2,5-Dicyano-1,4-phenylenevinylene-Synthetic Tuning of the HOMO and LUMO Energy Levels of Conjugated Polymers

Abstract: A series of copolymers of 2,5-dicyano-1,4-phenylenevinylene and 2-methoxy-5-(2'-ethylhexyloxy)-1,4-phenylenevinylene were synthesized by Wittig reaction. The HOMO and LUMO energy levels of copolymers can be easily tuned by controlling the feed ratio of co-monomers.

Cited by 30 publications

References 12 publications

Synthetic Aspects and Electro-Optical Properties of Fluorinated Arylenevinylenes for Luminescence and Photovoltaics

Synthetic Aspects and Electro-Optical Properties of Fluorinated Arylenevinylenes for Luminescence and Photovoltaics

Five Orders-of-Magnitude Enhancement of Two-Photon Absorption for Dyes on Silver Nanoparticle Fractal Clusters

Effective adjustment of the optoelectronic properties of organic conjugated materials by synthesizing p-n diblock molecules

Contact Info

Product

Resources

About