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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 28, Number 8
BKCSDE 28(8)
August 20, 2007 

Synthesis, Photophysical and Electrochemical Properties of Novel Conjugated Donor-Acceptor Molecules Based on Phenothiazine and Benzimidazole
Xiao-Hang Zhang, Seon Ho Kim, In Su Lee, Chun Ji Gao, Sung Ik Yang*, Kwang-Hyun Ahn*
Phenothiazine, Benzimidazole, Charge transfer, Donor-acceptor, Fluorophore
Two series of new organic fluorophores such as asymmetrical 3-(benzimidazol-2-yl)-10-hexylphenothiazine derivatives 1 and symmetrical 3,7-bis(benzimidazol-2-yl)-10-hexylphenothiazine derivatives 2 have been synthesized. Electronic absorption, fluorescence, and electrochemistry measurements reveal that the electron withdrawing benzimidazole subunit directly connected to the phenothiazine core facilitates the charge transfer characters which were also verified by the theoretical calculations. Various substituents on the benzimidazole moieties can allow a fine-tuning of the LUMO energy levels of the molecules without significantly affecting the HOMO energy levels. The method provides a new route for designing ambipolar molecules whose energy levels are well-matched with the Fermi levels of the electrodes to facilitate the electron or hole injection/transfer in OLED devices.
1389 - 1395
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