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Title
Japanese: 
English:Synthesis and Properties of B4N4-Heteropentalenes Fused with Polycyclic Hydrocarbons 
Author
Japanese: 菓子田 惇輝, 庄子 良晃, H. Taka, 福島 孝典.  
English: J. Kashida, Y. Shoji, H. Taka, T. Fukushima.  
Language English 
Journal/Book name
Japanese: 
English:Chemistry European Journal 
Volume, Number, Page Volume 29    Issue 19    e202203561
Published date Feb. 3, 2023 
Publisher
Japanese: 
English: 
Conference name
Japanese: 
English: 
Conference site
Japanese: 
English: 
Official URL https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202203561
 
DOI https://doi.org/10.1002/chem.202203561
Abstract Hybrid molecules of π-conjugated carbon rings and BN-heterocyclic rings (h-CBNs) fused with each other have been a rare class of compounds due to the limited availability of their synthetic methods. Here we report the synthesis of new h-CBNs featuring a B4N4-heteropentalene core and polycyclic aromatic hydrocarbon wings. Using 1,2-azaborinine derivatives as a building block, we developed a rational synthetic protocol that allows the formation of a B4N4 ring in a stepwise manner, resulting in the fully fused ABA-type triblock molecules. Thus, three derivatives of 1 bearing naphthalene (1Naph), anthracene (1Anth), or phenanthrene (1Phen) wings fused with the B4N4 core were synthesized and characterized. Among them, 1Phen, which displays the highest triplet-state energy, was found to serve a host material for phosphorescent OLED devices, for which a maximum external quantum efficiency of 13.7 % was recorded. These findings may promote the synthesis of various types of h-CBNs aiming at new properties arising from the synergy of two different π-electronic systems.

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