The Non‐radiative Dissipation of Excitation Energy in Solid Cinnamic Acid by Dimer Formation

Rennert, J.; Ruggiero, E. M.; Rapp, J.

doi:10.1111/j.1751-1097.1967.tb08787.x

Cited by 21 publications

(9 citation statements)

References 8 publications

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“…Furthermore,t his concept of solubility modulation was investigated for its application in solution phase processed OLEDs.The synthesized fluorene copolymer was used as the emitting layer in an OLED with as imple stack architecture. [25,26] In the presence of an ortho-hydroxy group, trans to cis isomerization leads to the irreversible formation of coumarin with water or an alcohol leaving group (Scheme 2). Thes ynthesis of monomer 3 (Scheme 1) started from commercially available 4-(dibutylamino)salicylaldehyde, which was first converted by aW ittig reaction into a transcinnamic acid ester.…”

Section: Methodssupporting

confidence: 54%

“…Light‐induced isomerization of the double bond of cinnamates is well‐documented 25. 26 In the presence of an ortho ‐hydroxy group, trans to cis isomerization leads to the irreversible formation of coumarin with water or an alcohol leaving group (Scheme ) 27. 28 The formation of the coumarin generates a strongly emissive species at λ =440 nm which allows easy monitoring of the reaction progress, as shown by Jullien and co‐workers, through detecting the increasing emission of coumarin 17.…”

Section: Methodsmentioning

confidence: 99%

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Light‐Induced Solubility Modulation of Polyfluorene To Enhance the Performance of OLEDs

et al. 2015

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Liquid-phase processing is a key prerequisite for the cost-efficient fabrication of organic electronic devices. We report an approach for light-induced modulation of the solubility of π-conjugated polymers (polyfluorene) with side chains functionalized with hydroxycinnamic acid. Irradiation with light cleaves the solubilizing side chains and renders the thin films of the polyfluorene insoluble. In a proof of concept device, polyfluorenes were applied as emissive layers in OLEDs. Photoirradiation of the emission layer leads to an increase in OLED performance combined with a modulation of the solubility of the thin film. These results offer the possibility for further development in terms of manipulating the solubility and emissive parameters of an important class of functional materials.

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Section: Methodssupporting

confidence: 54%

Section: Methodsmentioning

confidence: 99%

Light‐Induced Solubility Modulation of Polyfluorene To Enhance the Performance of OLEDs

et al. 2015

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“…The basic concepts of topochemistry 1) initially developed for interpreting the [2 + 2] photocycloaddition of monoolefinic chromophores in the crystalline state have been successfully extended to crystalline compounds bearing two independent reactive groups, thus opening the route to solid state step-growth photopolymerization proceeding under strict control of the crystal lattice 2) . The original photodimerization reaction exhibited by various crystalline forms of cinnamic acid 3,4) , which is still a subject of academic interest 5) , has been adapted some four decades ago for obtaining organic photo-imaging system based on photocross-linkable polymers 6) . Poly(vinyl cinnamate) (PV-Cin) is the forerunner of this group of photopolymers working as a negative resist 7) .…”

Section: Introductionmentioning

confidence: 99%

Photoreactivity of polymers with dimerizable side-groups: Kinetic analysis for probing morphology and molecular organization

Coqueret¹

1999

Macromol. Chem. Phys.

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SUMMARY:The solid state photoreactivity of polymers with pendant chromophores of the cinnamic type has been examined by monitoring the reaction by UV spectroscopy. Two series of photosensitive polymers with polysiloxane or polyvinylamine main chains were selected to exemplify specific behaviors contrasting on various aspects with that of poly(vinyl cinnamate) as the reference photocross-linkable polymer. Valuable kinetic information was obtained from simple photoirradiation experiments for probing the physical structure of the condensed polymeric material and for studying the influence of chromophore content. Photoisomerization of the chromophore competes efficiently with dimerization for both the liquid polysiloxanes with cinnamic esters connected by long spacers and for the glassy cinnamoylated polyvinylamines, the density of sites paired for dimerization being expectedly low in these amorphous matrices. The variations of the quantum yield for dimerization in the neat polymers as a function of their composition are discussed and correlated to the changes of practical sensitivity for photocuring. For polysiloxanes with pendant cyanostyrylacrylic groups, the leveled reactivity observed with quantum yields at zero conversion independent on the macroscopic chromophore content in the samples is explained by phase separation leading to dispersed domains rich in photoreactive side-groups. The layered order evidenced by wide angle X-ray scattering is consistent with the clean and reversible photoreaction. In spite of the discussed structural differences, the variation of the normalized quantum yield for dimerization U Dim /U 0 as a function of conversion p is described by the same scaling law U Dim /U 0 = (1-p) 3 as was established for the amorphous and homogeneous samples of cinnamoylated polysiloxanes or polyvinylamines.

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“…12,13 For photo-cross-linking, cinnamates have gained attention, as they readily undergo [2 + 2] cycloaddition when exposed to UV irradiation. 14,15 In contrast to other photo-cross-linking protocols, cinnamates do not require additives like photo-acids. 16 Additionally, the optical properties of cinnamates are easily tailored to external demands by attaching electron donating or withdrawing groups to the chromophore.…”

Section: ■ Introductionmentioning

confidence: 99%

Photo-Cross-Linkable Polymeric Optoelectronics Based on the [2 + 2] Cycloaddition Reaction of Cinnamic Acid

Schelkle¹,

Bender²,

Beck³

et al. 2016

Macromolecules

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We report the synthesis of cinnamic acid-functionalized conjugated polymers, which are cross-linked via [2 + 2] cycloaddition by UV illumination, reducing their solubility. The cross-linking reaction was investigated by a combination of FTIR and optical spectroscopy, and an optimum condition for the solubility modulation of thin films, a major challenge in the solution-phase fabrication of layered optoelectronic devices, was reached. As proof of concept, OLEDs were fabricated, using these conjugated polymers as emissive layers.

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The Non‐radiative Dissipation of Excitation Energy in Solid Cinnamic Acid by Dimer Formation

Cited by 21 publications

References 8 publications

Light‐Induced Solubility Modulation of Polyfluorene To Enhance the Performance of OLEDs

Light‐Induced Solubility Modulation of Polyfluorene To Enhance the Performance of OLEDs

Photoreactivity of polymers with dimerizable side-groups: Kinetic analysis for probing morphology and molecular organization

Photo-Cross-Linkable Polymeric Optoelectronics Based on the [2 + 2] Cycloaddition Reaction of Cinnamic Acid

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