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Unveiling 79‐Year‐Old Ixene and Its BN‐Doped Derivative
Author(s) -
Pati Palas Baran,
Jin Eunji,
Kim Yohan,
Kim Yongchul,
Mun Jinhong,
Kim So Jung,
Kang Seok Ju,
Choe Wonyoung,
Lee Geunsik,
Shin HyungJoon,
Park Young S.
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202004049
Subject(s) - heteroatom , doping , scanning tunneling microscope , organic electronics , derivative (finance) , materials science , band gap , electrochemistry , electronic structure , nanotechnology , chemistry , crystallography , optoelectronics , computational chemistry , organic chemistry , physics , transistor , ring (chemistry) , electrode , quantum mechanics , voltage , financial economics , economics
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 (B 2 N 2 ‐ixene), and their characterizations. Compared to ixene, B 2 N 2 ‐ixene absorbs longer‐wavelength light and has a smaller electrochemical energy gap. In addition to its single‐crystal structure, scanning tunneling microscopy revealed that B 2 N 2 ‐ixene adopts a nonplanar geometry on a Au(111) surface. The experimentally obtained electronic structure of B 2 N 2 ‐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 π‐conjugation that can be used in versatile organic electronics applications.