Photodecomposition of commercial polysulphones and model diaryl sulphones

Abdul-Rasoul, Firas A. M.; Catherall, Colin L. R.; Hargreaves, John S.; Mellor, John M.; Phillips, David

doi:10.1016/0014-3057(77)90175-6

Cited by 24 publications

(8 citation statements)

References 11 publications

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“…For example, facile decomposition of diphenyl sulfone (DPS) has been observed. [53][54][55][56][57] DPS and related compounds decompose via homolytic cleavage of one of the two formally single bonds connecting the sulfur atom to an aromatic ring, a process which characterized by an activation energy of 8.5-8.8 kcal/mol. 57 …”

Section: Degradation In Host Moleculesmentioning

confidence: 99%

Theoretical investigation of the degradation mechanisms in host and guest molecules used in OLED active layers

2014

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A feature of OLEDs that has to date received little attention is the prediction of the stability of the molecules involved in the electrical and optical processes. Here, we present computational results intended to aid in the development of stable systems. We identify degradation pathways and define new strategies to guide the synthesis of stable materials for OLED applications for both phosphorescent emitters and organic host materials. The chemical reactivity of these molecules in the active layers of the devices is further complicated by the fact that, during operation, they can be either oxidized or reduced (as they localize a hole or an electron) in addition to forming both singlet and triplet excitons.

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Section: Degradation In Host Moleculesmentioning

confidence: 99%

Theoretical investigation of the degradation mechanisms in host and guest molecules used in OLED active layers

2014

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“…[85][86][87][88][89][90][91][92][93][94][95][96][97] Waksman 85 compares spectral transmittance results with frequently-used solar transmittance values. These materials are frequently studied by visible spectrophotometry.…”

Section: Visible Spectrophotometrymentioning

confidence: 99%

“…Confocal Raman microscopy was also used to demonstrate gradual increase in crystallinity of surface regions of naturally aged polyethylene. 254 13.11 NUCLEAR MAGNETIC RESONANCE 1 H NMR and 13 C NMR spectra 94,95,114,127,131,132,146,150,159,163,179,182,201,208,213,215,217,[255][256][257][258][259][260][261][262][263][264] were used to characterize changes in polysulfones, unsaturated polyester resins, polyurethanes, polyethylene, polyacetal, polystyrene, dyed fibers, and coatings. 252,253 Non-destructive properties of the method are important in these studies.…”

Section: Raman Spectroscopymentioning

confidence: 99%

Testing Methods of Weathered Specimen

Wypych¹

2013

Handbook of Material Weathering

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“…For example, diphenylsulfone (DPSO) has long been known to decompose under UV irradiation via cleavage of the S-C bond. 19,[47][48][49][50][51] Ponterini and Momicchioli presented a detailed study of the triplet decay mechanism for the photodissociation in DPSO using laser flash photolysis, 51 providing a dissociation mechanism of the S-C bond that involves two triplet excited states: a lower energy phenyl-localized 3 * state and a higher lying C-S 3 * state. Excitation to the lowest phenyl 3 * state can be followed by conversion into the 3 * state with a potential energy barrier of ca.…”

Section: Introductionmentioning

confidence: 99%

“…Combined with their high triplet energies, aryl SO 2 and aryl PO derivatives have been used in the development of host materials that inhibit self-quenching of the light-emitting guests in both blue phosphorescent − and TADF OLEDs. − In addition, such aryl SO 2 and aryl PO-based host materials exhibit good thermal stabilities. − Unfortunately, however, some of these materials decompose under UV irradiation or in electrically stressed devices, which limits material lifetime. For example, diphenylsulfone (DPSO) has long been known to decompose under UV irradiation via cleavage of the S–C bond. ,− Ponterini and Momicchioli presented a detailed study of the triplet decay mechanism for the photodissociation in DPSO using laser flash photolysis, providing a dissociation mechanism of the S–C bond that involves two triplet excited states: a lower energy phenyl-localized 3 ππ* state and a higher lying C–S 3 σσ* state. Excitation to the lowest phenyl 3 ππ* state can be followed by conversion into the 3 σσ* state with a potential energy barrier of ca.…”

Section: Introductionmentioning

confidence: 99%

Chemical Stabilities of the Lowest Triplet State in Aryl Sulfones and Aryl Phosphine Oxides Relevant to OLED Applications

Hong

Scarpaci

et al. 2019

Chem. Mater.

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Aryl sulfones and phosphine oxides are widely used as molecular building blocks for host materials in the emissive layers of organic light-emitting diodes. In this context, the chemical stability of such molecules in the triplet state is of paramount concern to long-term device performance. Here, we explore the triplet excited-state (T 1) chemical stabilities of aryl sulfonyl and aryl phosphoryl molecules by means of UV absorption spectroscopy and density functional theory calculations. Both the sulfur-carbon bonds of the aryl sulfonyl molecules and the phosphorus-carbon bonds of aryl phosphoryl derivatives are significantly more vulnerable to dissociation in the T 1 state when compared to the ground (S 0) state. Although the vertical S 0 →T 1 transitions correspond to non-bonding→-orbital transitions, geometry relaxations in the T 1 state lead to -* character over the respective sulfur-carbon or phosphorus-carbon bond, a result of significant electronic state mixing, which facilitates bond dissociation. Both the activation energy for bond dissociation and the bond dissociation energy in the T 1 state are found to vary linearly with the adiabatic T 1-state energy. Specifically as T 1 becomes more energetically stable, the activation energy becomes larger, and dissociation becomes less likely, i.e., more endothermic or less exothermic. While substitutions of electron-donating or accepting units onto the aryl sulfones and aryl phosphine oxides have only marginal influence on the dissociation reactions, extension of the -conjugation of the aryl groups leads to a significant reduction in the triplet energy and a considerable enhancement in the T 1-state chemical stabilities.

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Photodecomposition of commercial polysulphones and model diaryl sulphones

Cited by 24 publications

References 11 publications

Theoretical investigation of the degradation mechanisms in host and guest molecules used in OLED active layers

Theoretical investigation of the degradation mechanisms in host and guest molecules used in OLED active layers

Testing Methods of Weathered Specimen

Chemical Stabilities of the Lowest Triplet State in Aryl Sulfones and Aryl Phosphine Oxides Relevant to OLED Applications

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