Synthesis and Properties of B4N4‐Heteropentalenes Fused with Polycyclic Hydrocarbons
Synthesis and Properties of B4N4‐Heteropentalenes Fused with Polycyclic Hydrocarbons
复制标题
多环烃稠合B4N4-杂戊二烯的合成及性能
DOI：
10.1002/chem.202203561
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发表时间：
2023
期刊：
影响因子：
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通讯作者：
Fukushima Takanori
中科院分区：
文献类型：
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作者：
Kashida Junki;Shoji Yoshiaki;Taka Hideo;Fukushima Takanori
π-共轭碳环和BN-杂环(h-CBN)相互融合的杂化分子由于其合成方法的局限性而成为一类罕见的化合物。在这里，我们报道了具有B4N4-杂戊烯核和多环芳烃侧翼的新的h-CBN的合成。以1，2-氮杂硼烷衍生物为基础，我们开发了一种合理的合成方案，允许以一种循序渐进的方式形成B4N4环，从而得到完全融合的ABA型三嵌段分子。因此，我们合成并表征了三种与B4N4核融合的1-含萘(1Naph)、菲(1Anth)或菲(1Phen)的衍生物。其中，显示出最高三重态能量的1Phen被发现是磷光有机发光器件的主体材料，其最大外量子效率为13.7 %。这些发现可能会促进各种类型的h-CBN的合成，旨在通过两个不同的π-电子系统的协同作用产生新的性质。
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 B4N4ring in a stepwise manner, resulting in the fully fused ABA‐type triblock molecules. Thus, three derivatives of1bearing naphthalene (1Naph), anthracene (1Anth), or phenanthrene (1Phen) wings fused with the B4N4core 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.