Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 1, Pages 196-203Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo502296z
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Funding
- AcRF Tier 1 from MOE [RG 16/12]
- AcRF Tier 2 from MOE [ARC 20/12, ARC 2/13]
- CREATE program (Nanomaterials for Energy and Water Management) from NRF, Singapore
- National Natural Science Foundation of China (NSFC) [21102150]
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It is very challenging to introduce azaborine into an electron-deficient arene system because of unfavorable intramolecular electrophilic borylation reaction. In this report, we adopted a straightforward methodology to construct a large BN-embedded pi-system based on perylene diimide (PDI), which is the first BN-annulation example with highly electron-withdrawing polycyclic aromatic hydrocarbons. The physical properties of the as-prepared N,N-dicyclohexyl-1-aza-12-bora-benzoperylene diimide (PDI-1BN) have been fully studied, and its sensing behavior to fluoride ion as well as its OLED performance was also investigated.
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