Bipolar thianthrene derivatives exhibiting room temperature phosphorescence for oxygen sensing

Ausra Tomkeviciene, Asta Dabulienė, Tomas Matulaitis, Matas Guzauskas, Viktorija Andruleviciene, Juozas Vidas Grazulevicius, Yuri Yamanaka, Yoshio Yano, Toshikazu Ono

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Abstract

The series of donor-acceptor (D-A) compounds consisting of a thianthrene donor and either a benzophenone or a diphenylsulfone acceptor units were designed and synthesized via Suzuki cross-coupling. By varying the number of donor units, as well as by introducing heavy atom (Br) into the molecular structure the impact of these substituents on the thermal, electrochemical and emissive properties of the compounds was studied. The compound containing two thianthrene units appeared to have higher thermal stability and higher glass transition temperature than monosubstituted derivative. All thianthrenyl substituted benzophenone or diphenylsulfone compounds showed bipolar behavior. Strong room temperature phosphorescence and dual fluorescence-phosphorescence were observed at room temperature. The compounds containing stronger electron acceptor diphenylsulfone demonstrated a two-fold higher photoluminescence quantum yield values up to 19% in rigid Zeonex® films than that benzophenone derivatives. The crystals of some synthesized compounds demonstrated oxygen sensing ability.

Original languageEnglish
Article number107605
JournalDyes and Pigments
Volume170
DOIs
Publication statusPublished - Nov 2019

All Science Journal Classification (ASJC) codes

  • Chemical Engineering(all)
  • Process Chemistry and Technology

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    Tomkeviciene, A., Dabulienė, A., Matulaitis, T., Guzauskas, M., Andruleviciene, V., Grazulevicius, J. V., Yamanaka, Y., Yano, Y., & Ono, T. (2019). Bipolar thianthrene derivatives exhibiting room temperature phosphorescence for oxygen sensing. Dyes and Pigments, 170, [107605]. https://doi.org/10.1016/j.dyepig.2019.107605