The Impact of C2 Insertion into a Carbazole Donor on the Physicochemical Properties of Dibenzo[a,j]phenazine-Cored Donor-Acceptor-Donor Triads

Paola Zimmermann Crocomo, Takahito Kaihara, Soki Kawaguchi, Patrycja Stachelek, Satoshi Minakata, Piotr de Silva*, Przemyslaw Data*, Youhei Takeda*

*Corresponding author for this work

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Novel electron donor-acceptor-donor (D-A-D) compounds comprising dibenzo[a,j]phenazine as the central acceptor core and two 7-membered diarylamines (iminodibenzyl and iminostilbene) as the donors have been designed and synthesized. Investigation of their physicochemical properties revealed the impact of C2 insertion into well-known carbazole electron donors on the properties of previously reported twisted dibenzo[a,j]phenazine-core D-A-D triads. Slight structural modification caused a drastic change in conformational preference, allowing unique photophysical behavior of dual emission derived from room-temperature phosphorescence and triplet-triplet annihilation. Furthermore, electrochemical analysis suggested sigma-dimer formation and electrochemical polymerization on the electrode. Quantum chemical calculations also rationalized the experimental results.
Original languageEnglish
JournalChemistry: A European Journal
Issue number53
Pages (from-to)13390-13398
Number of pages9
Publication statusPublished - 2021


  • Charge transfer
  • Donor-acceptor
  • Fluorescence
  • Organic light-emitting diodes
  • Triplet-triplet annihilation


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