Dataset Information

Synthesis, Electronic Properties and OLED Devices of Chromophores Based on ?5 -Phosphinines.

ABSTRACT: A new series of 2,4,6-triaryl-?5 -phosphinines have been synthesized that contain different substituents both on the carbon backbone and the phosphorus atom of the six-membered heterocycle. Their optical and redox properties were studied in detail, supported by in-depth theoretical calculations. The modularity of the synthetic strategy allowed the establishment of structure-property relationships for this class of compounds and an OLED based on a blue phosphinine emitter could be developed for the first time.

SUBMITTER: Pfeifer G

PROVIDER: S-EPMC7496645 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Publications

Synthesis, Electronic Properties and OLED Devices of Chromophores Based on λ<sup>5</sup> -Phosphinines.

Pfeifer Gregor G Chahdoura Faouzi F Papke Martin M Weber Manuela M Szűcs Rózsa R Geffroy Bernard B Tondelier Denis D Nyulászi László L Hissler Muriel M Müller Christian C

Chemistry (Weinheim an der Bergstrasse, Germany) 20200806 46

A new series of 2,4,6-triaryl-λ<sup>5</sup> -phosphinines have been synthesized that contain different substituents both on the carbon backbone and the phosphorus atom of the six-membered heterocycle. Their optical and redox properties were studied in detail, supported by in-depth theoretical calculations. The modularity of the synthetic strategy allowed the establishment of structure-property relationships for this class of compounds and an OLED based on a blue phosphinine emitter could be deve ...[more]

PMID: 32092780

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Project description:Diketopyrrolopyrroles (DPP) have been recognized as a promising acceptor unit for construction of semiconducting donor-acceptor (D-A) polymers, which are typically flanked by spacers such as thiophene rings via a carbon-carbon single bond formation. It may suffer from a decrease in the coplanarity of the molecules especially when bulky side chains are installed. In this work, the two N atoms in the DPP unit are further fused with C-3 of the two flanking thiophene rings, yielding a π-expanded, very planar fused-ring building block (DPPFu). A novel DPPFu-based D-A copolymer (PBDTT-DPPFu) was successfully synthesized, consisting of a benzo[1,2-b:4,5-b']dithiophene (BDTT) unit as a donor and a DPPFu unit as an acceptor. For comparison, the unfused DPP-based counterpart PBDTT-DPP was also synthesized. Two dodecyl alkyl chains were attached to thiophene rings of DPP moieties to ensure good solubility of the DPPFu-based polymer. The influence of the ring-fusion effect on their structure, photophysical properties, electronic properties, molecular packing, and charge transport properties is investigated. Ring-fusion enhances the intermolecular interactions of PBDTT-DPPFu polymer chains as indicated by density functional theory calculation and analysis of electrostatic potential and van der Waals potential and results in significantly improved molecular packing for both the in-plane and out-of-plane directions as suggested by X-ray measurements. Finally, we correlate the molecular packing to the device performance by fabricating field-effect transistors based on these two polymers. The charge carrier mobility of the ring-fused polymer PBDTT-DPPFu is significantly higher as compared to the PBDTT-DPP polymer without ring-fusion, although PBDTT-DPPFu exhibited a much lower number-average molecular weight of 17 kDa as compared to PBDTT-DPP with a molecular weight of 108 kDa. The results from our comparative study provide a robust way to increase the interchain interaction by ring-fusion-promoted coplanarity.

Dataset Information

Synthesis, Electronic Properties and OLED Devices of Chromophores Based on ?5 -Phosphinines.

Publications

Synthesis, Electronic Properties and OLED Devices of Chromophores Based on λ<sup>5</sup> -Phosphinines.

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