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Published on: April 1, 2013
Phenanthrene-Fused BN-Acenaphth(yl)ene: Synthesis, Structures, and Photophysical Studies
Zhongzan Liu1, Jiahao Cui2, Yiqing Liu1
1Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384, People's Republic of China.
None:
Two novel BN-doped CP-PAHs, BN-ANH-TPh and BN-AN-TPh, were synthesized in a straightforward manner. BN-ANH-TPh features a localized C-C bond in the five-membered ring, whereas BN-AN-TPh features a localized C═C bond. Notably, BN-AN-TPh was obtained via the dehydrogenation of BN-ANH-TPh. Both compounds were unambiguously characterized by single-crystal X-ray diffraction analysis. A subtle structural alteration from C-C to C═C bonding resulted in significant modulation of their electronic structures and photophysical properties. Compared to BN-ANH-TPh, BN-AN-TPh exhibits lower LUMO and HOMO energy levels, accompanied by a narrower HOMO-LUMO energy gap. BN-AN-TPh exhibits red-shifted absorption and emission spectra relative to those of BN-ANH-TPh. Both compounds emit strongly in solution, with quantum yields of 73% and 71%, respectively. Furthermore, organic light-emitting diodes (OLEDs) were fabricated by using BN-AN-TPh and BN-ANH-TPh as emissive layers. The OLED device based on BN-AN-TPh achieved a maximum current efficiency of 2.41 cd/A and a maximum luminance of 1556 cd/m2.
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