Luminescent poly(p-phenylenevinylene) with 4-methylcoumarin side groups: Synthesis, optical properties and photo-crosslinking behaviors

Tsai, Cheng‐Jang; Chen, Yun

doi:10.1016/j.reactfunctpolym.2006.03.016

Cited by 16 publications

(9 citation statements)

References 16 publications

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“…Tsai and Chen prepared a coumarin-appended PPV 80.4 by a Heck reaction (Scheme ). Efficient energy transfer from methylcoumarin to the PPV backbone occurs after photoexcitation. A double layer device (Al/PEDOT/PPV/ITO) displays green electroluminance.…”

Section: Photochemical Cross-linkingmentioning

confidence: 99%

Immobilization Strategies for Organic Semiconducting Conjugated Polymers

et al. 2018

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This Review details synthetic routes toward and properties of insoluble polymeric organic semiconductors obtained through desolubilization strategies. Typical applications include fixation of donor-acceptor bulk-heterojunction morphologies in organic photovoltaic cells, cross-linking of charge transport materials and active emitters in light emitting diodes or similar devices, and immobilization of morphologies in field effect transistors. A second important application is the structuring of organic semiconductors, using them as photoresists. After desolubilization, removal of the nonirradiated resist leads to elevated, micron-sized features of the semiconductor. In this Review, different strategies for desolubilization are covered. By photochemical or thermal cleavage of solubility-mediating groups such as esters, sulfonium salts, amides, ethers, and acetals or by retro-Diels-Alder reactions, volatile elimination products and the insoluble semiconductor are formed. In another case, desolubilization is achieved by cross-linking via functional groups present in the polymer side chains including vinyl, halide, silicone, boronic acid, and azide functionalities, which polymerize thermally or photochemically. Alternatively, small molecular additives such as photoacids, oligothiols, or oligoazides result in network formation in combination with compatible functional groups present in the immobilizable polymers. Advantages and disadvantages of the respective methods are discussed.

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Section: Photochemical Cross-linkingmentioning

confidence: 99%

Immobilization Strategies for Organic Semiconducting Conjugated Polymers

et al. 2018

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“…Keeping in mind the enormous importance of photolithography to electronics, it is not surprising that the concept of directly photopatternable organic electronic materials have found significant interest. [14][15][16][17][18][19][20][21][22][23][24][25][26] Our approach to photopatternable conjugated polymers rests on the concept that the vast majority of conjugated polymers require flexible side chains for solubility, and that their removal should render materials insoluble. In addition, solubilizing side chains causes several problems for organic electronic materials: i) they take up large fractions of active layer volume, ii) labile bonds in these chains are primary sources of photochemical decomposition, [27][28][29] iii) as they render most conjugated polymers soluble in the same solvents, fabricating stratified, multilayer devices using only solvent-based techniques can restrict the materials used to those that are orthogonally soluble.…”

Section: Photocleavable Side Chainsmentioning

confidence: 99%

Stimuli-responsive side chains for new function from conjugated materials

Thomas

Pawle

Smith

2016

Journal of Photochemistry and Photobiology A: Chemistry

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This article describes several projects in our laboratory relating to stimuliresponsive conjugated materials using functional side chain moieties. Although side chain engineering has become increasingly important in controlling the packing of conjugated materials, these groups have typically been reserved for imparting solubility to otherwise insoluble materials. By incorporating solubilizing side chains through photocleavable nitrobenzyl linkers, new conjugated polymers behave as negative photoresists upon exposure to ultraviolet light with minimal photobleaching. Our approach enables photopatterning and solution-based fabrication of multilayer conjugated polymer films without the use of orthogonally soluble materials. Work to understand the electronic effects of the aromatic side chain substituents in these materials led to the subsequent discovery of aromatic interactions between side chains and main chains that control the conformations of solid-state phenylene-ethynylene oligomers, including highly twisted conjugated backbones. Such materials, when appropriately substituted, display reversible piezochromic and mechanofluorochromic behavior.

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“…Heck cross-coupling is an important method for carbon–carbon bond synthesis, and has greatly attracted more and more attention for its wide application in the synthesis of dyes, medicines, natural products, pesticides, perfumes, cinnamic acid derivatives, and new polymer materials [ 1 , 2 , 3 , 4 , 5 ]. The palladium-catalyzed Mizoroki–Heck cross-coupling reaction represents one of the most valuable methods for carbon–carbon bond formation in organic synthesis [ 6 , 7 ].…”

Section: Introductionmentioning

confidence: 99%

O-Carboxymethyl Chitosan Supported Heterogeneous Palladium and Ni Catalysts for Heck Reaction

Zhang

2017

Molecules

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Two polymer catalysts (Pd-OCMCS and Ni-OCMCS) with good reusability were synthesized by coordinating Pd and Ni onto O-carboxymethyl chitosan (OCMCS). The chemical structure and thermal stability of prepared catalysts were determined by Fourier transform infrared (FT-IR) spectra, Energy Dispersive Spectrometer (EDS)analysis, X-ray diffraction (XRD), and thermogravimetric analyzer (TG-DTG), and the analysis results showed that the Pd and Ni ions coordinated onto the OCMCS and formed a ligand with the –COOH group, amino groups, and –OH group on the OCMCS, and the EDS and Inductively Coupled Plasma Optical Emission Spectrometry (ICP-OES) analysis results showed that the loading amounts of Pd and Ni were approximately 8.3% and 8.9%, respectively. In the Heck reaction between aryl halides and n-butyl acrylate catalyzed by the prepared catalyst, the test results showed that the product yield followed the order of aryl iodide > aryl bromide > aryl chloride. Additionally, the product yield for the aryl iodide and aryl bromide could reach up to 99% and 96%, respectively. Moreover, the electron-withdrawing and electron-donating property of the group on the aryl also affected the product yield, and the product yield for aryl halides with electron-withdrawing group p-NO2, p-CH3CO, and p-CHO was higher than that with electron-donating group p-CH3.

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Luminescent poly(p-phenylenevinylene) with 4-methylcoumarin side groups: Synthesis, optical properties and photo-crosslinking behaviors

Cited by 16 publications

References 16 publications

Immobilization Strategies for Organic Semiconducting Conjugated Polymers

Immobilization Strategies for Organic Semiconducting Conjugated Polymers

Stimuli-responsive side chains for new function from conjugated materials

O-Carboxymethyl Chitosan Supported Heterogeneous Palladium and Ni Catalysts for Heck Reaction

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