Graduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan.
Digital Monozukuri (Manufacturing) Education and Research Center, Hiroshima University, Higashi-Hiroshima 739-0046, Japan.
Dalton Trans. 2023 Jul 11;52(27):9389-9397. doi: 10.1039/d3dt01841e.
Tricoordinate boron-incorporated π-conjugated systems are widely investigated as optoelectronic materials because of their unique p-π* orbital interactions and high Lewis acidity. Among them, thiophene-fused diborinines are characterized by moderate antiaromaticity and extended conjugation. In this work, we have developed two new dithienodiborinines with and symmetries, which exhibited completely different optical properties. The thiophene-fused diborinines synthesized in this study showed excellent fluorescence properties both in solution and in the solid state, with quantum yields of up to 95%. The high antiaromaticity enhanced the Lewis acidity of the boron centers, as proven by the large association constants with fluoride ion estimated from titration experiments. The high Lewis acidity and the superior luminescence property have enabled their application as fluorescent sensor materials for the detection of ammonia vapor.
三配位硼取代的π共轭体系因其独特的 p-π* 轨道相互作用和高路易斯酸度而被广泛研究作为光电材料。其中，噻吩并二硼嗪具有适度的反芳香性和扩展的共轭性。在这项工作中，我们开发了两种具有 和 对称性的新型二噻吩二硼嗪，它们表现出完全不同的光学性质。本研究中合成的噻吩并二硼嗪在溶液和固态中均表现出优异的荧光性质，量子产率高达 95%。高反芳香性增强了硼中心的路易斯酸度，这可以通过滴定实验估算的与氟离子的大缔合常数来证明。高路易斯酸度和优越的发光性能使它们能够作为荧光传感器材料，用于检测氨蒸气。
