Unveiling 79-year-old ixene and its BN-doped derivative
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- Unveiling 79-year-old ixene and its BN-doped derivative
- Pati, Palas Baran; Jin, Eunji; Kim, Yohan; Kim, Yongchul; Mun, Jinhong; Kim, So Jung; Kang, Seok Ju; Choe, Wonyoung; Lee, Geunsik; Shin, Hyung-Joon; Park, Young S.
- Issue Date
- WILEY-V C H VERLAG GMBH
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.59, no.35, pp.14891 - 14895
- Polycyclic aromatic hydrocarbons (PAHs) are key components of organic electronics. The electronic properties of these carbon-rich materials can be controlled through doping with heteroatoms such as B and N, however, few convenient syntheses of BN-doped PAHs have been reported. Described herein is the rationally designed, two-step syntheses of previously unknown ixene and BN-doped ixene (B2N2-ixene), and their characterizations. Compared to ixene, B2N2-ixene absorbs longer-wavelength light and has a smaller electrochemical energy gap. In addition to its single-crystal structure, scanning tunneling microscopy revealed that B2N2-ixene adopts a nonplanar geometry on a Au(111) surface. The experimentally obtained electronic structure of B2N2-ixene and the effect of BN-doping were confirmed by DFT calculations. This synthesis enables the efficient and convenient construction of BN-doped systems with extended pi-conjugation that can be used in versatile organic electronics applications.
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