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Postfunctionalization of BN‐Embedded Polycyclic Aromatic Compounds for Fine‐Tuning of Their Molecular Properties
Author(s) -
Wang XiaoYe,
Yang DongChu,
Zhuang FangDong,
Liu JiaJie,
Wang JieYu,
Pei Jian
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201501161
Subject(s) - knoevenagel condensation , halogenation , electrophile , chemistry , thiophene , aromaticity , molecule , planar , combinatorial chemistry , organic chemistry , computational chemistry , nanotechnology , catalysis , materials science , computer science , computer graphics (images)
New BN‐embedded, thiophene‐fused, polycyclic aromatic compounds with planar geometry were designed and synthesized. The molecules showed excellent stability and chemical robustness. Postfunctionalization on this skeleton was demonstrated with a series of electrophilic bromination, palladium‐catalyzed cross‐coupling, and Knoevenagel condensation reactions. The π skeleton remained intact during these late‐stage transformations. The optical and electronic properties have been well tuned through incorporation of electron‐rich and ‐deficient groups on the backbone. This work shows the great advantage of the postfunctionalization strategy on BN‐containing polycyclic aromatic compounds for fast diversification and materials screening.