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Issue 114, 2015
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Structure–property studies of P-triarylamine-substituted dithieno[3,2-b:2′,3′-d]phospholes

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The synthesis of 10 novel P-substituted dithienophosphole oxide compounds applying phenylcarbazole and indolocarbazole donors is presented. Based on photo-physical and theoretical investigations, the study reveals that the pyramidal geometry of the phosphorus allows for the synthesis of charge transfer materials by introducing strong exocyclic donor groups but suppresses intramolecular charge transfer below a certain donor strength threshold, which is an appealing structural feature for the design of donor–acceptor materials. The triplet energies of the phenylcarbazole based compounds are in the range of 2.49–2.65 eV, sufficiently high for potential applications as host materials in PhOLEDs. By contrast, the introduction of indolocarbazole, the weakest employed donor, yields materials exhibiting a significantly higher triplet energy of up to 2.87 eV and a remarkably low singlet–triplet splitting (0.18 eV). In addition an interesting example of an intramolecular electronic through-space interaction has been observed for the ortho-linked phenylcarbazole derivative.

Graphical abstract: Structure–property studies of P-triarylamine-substituted dithieno[3,2-b:2′,3′-d]phospholes

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Article information

12 Jul 2015
26 Oct 2015
First published
26 Oct 2015

RSC Adv., 2015,5, 93797-93807
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Author version available

Structure–property studies of P-triarylamine-substituted dithieno[3,2-b:2′,3′-d]phospholes

H. Puntscher, P. Kautny, B. Stöger, A. Tissot, C. Hametner, H. R. Hagemann, J. Fröhlich, T. Baumgartner and D. Lumpi, RSC Adv., 2015, 5, 93797
DOI: 10.1039/C5RA13651B

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