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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 34, Number 5
BKCSDE 34(5)
May 20, 2013 

Synthesis of New Spiro[benzo[c]fluorene-7,9'-fluorene] Dimers and Their Optical Properties
Jeong-A Seo, Chil-Won Lee, Myoung-Seon Gong*
Spirodimer, Spiro[benzofluorene-fluorene], High glass transition temperature, Blue host materials, OLED
Five novel spiro[benzo[c]fluorene-7,9'-fluorene] based dyes, including 5-[spiro[benzo[c]fluorene-7,9'-fluoren]-5- yl] spiro[benzo[c]fluorene-7,9'-fluorene] (7), 5-[spiro[benzo[c]fluorene-7,9'-fluoren]-9-yl] spiro[benzo[c]fluorene- 7,9'-fluorene] (8), 5-[spiro[benzo[c]fluorene-7,9'-fluoren]-2'-yl] spiro[benzo[c]fluorene-7,9'-fluorene] (9), 9- [spiro[benzo[c]fluorene-7,9'-fluoren]-9-yl] spiro[benzo[c]fluorene-7,9'-fluorene] (10), and 2'-[spiro[benzo[c]- fluorene-7,9'-fluoren]-2'-yl] spiro[benzo[c]fluorene-7,9'-fluorene] (11) were successfully prepared from the corresponding halogen and boronic acid derivatives through the Suzuki coupling reaction, respectively. Chemical structures were confirmed by 1H nuclear magnetic resonance (NMR), 13C NMR, Fourier transforminfrared spectrscopy, mass spectroscopy, and elemental analysis. The thermal properties were determined by differential scanning calorimetry and thermal gravimetric analysis. The relationships between the optical and electrochemical properties and the combined positions between these dimers were systematically investigated using UV-vis, photoluminescence (PL), and photoelectron spectroscopy. These five dimers exhibited high fluorescent quantum yields and good morphological stability with high glass transition states > 174 °C. Dimer 7 showed a UV absorbance peak at 353 nm, emission PL peak at 424 nm, and quantum efficiency of 0.62 in a cyclohexane solution.
1414 - 1420
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