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Synthesis and Properties of Benzo[d]dithieno[b,f]borepins
Organometallics ( IF 2.5 ) Pub Date : 2018-02-21 00:00:00 , DOI: 10.1021/acs.organomet.7b00844 Yohei Adachi 1 , Joji Ohshita 1
Organometallics ( IF 2.5 ) Pub Date : 2018-02-21 00:00:00 , DOI: 10.1021/acs.organomet.7b00844 Yohei Adachi 1 , Joji Ohshita 1
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Borepin is a seven-membered unsaturated ring system containing a tricoordinate boron. Although many borepin compounds annulated with aromatic systems have been reported to date, only one [b,d,f]-annulated tetracyclic borepins has been synthesized. In the present study, we synthesized benzo[d]dithieno[b,f]borepins as a new class of building blocks for functional materials motivated by the following structural features: (1) the high chemical stability of dithieno[b,f]borepin species; (2) the highly conjugated tetracyclic system with a borepin ring; and (3) electronic structures that are easily tuned by the introduction of functional groups on the annulated benzene ring. The prepared borepins were stable in air both in solution and as solids, and the electronic states could be finely tuned by changing the substituents on the benzene ring. Interestingly, DFT calculations revealed that the LUMO and LUMO+1 energy levels were strongly affected by the benzo[d]-annulation, depending on the boron-bridged positions on the fused thiophene rings. NICS and HOMA methods proved that the aromaticity of the borepin ring in the benzo[d]dithieno[b,f]borepin system is relatively small. We also report an unexpected red emission observed for the first time in borepin compounds for benzo[d]dithieno[b,f]borepin in the solid state.
中文翻译：
苯并[ d ]二硫代[ b，f ] borepins的合成及性质
硼异戊烯是含有三配位硼的七元不饱和环系。尽管迄今已报道了许多用芳族体系环化的硼异氰酸酯化合物，但仅合成了一种[ b，d，f ]环化的四环硼异氰酸酯。在本研究中，我们合成苯并[ d ]噻吩并[ b，˚F ] borepins作为一类新建立用于通过以下结构特征动机功能材料块组成：（1）二噻吩的化学稳定性高[ b，˚Fborepin物种；（2）具有孔销环的高共轭四环体系；（3）通过在苯环上引入官能团而易于调节的电子结构。所制得的销钉在空气中无论在溶液中还是固体中都是稳定的，可以通过改变苯环上的取代基来微调电子状态。有趣的是，DFT计算表明，LUMO和LUMO + 1的能级受苯并[ d ]环的强烈影响，这取决于稠合噻吩环上硼桥联的位置。NICS和HOMA方法证明，苯并[ d ]二噻吩并[ b，fborepin系统相对较小。我们还报告了首次在硼销化合物中观察到固态的苯并[ d ] dithieno [ b，f ]硼氢化萘的意外红色发射。
更新日期：2018-02-22
中文翻译：
苯并[ d ]二硫代[ b，f ] borepins的合成及性质
硼异戊烯是含有三配位硼的七元不饱和环系。尽管迄今已报道了许多用芳族体系环化的硼异氰酸酯化合物，但仅合成了一种[ b，d，f ]环化的四环硼异氰酸酯。在本研究中，我们合成苯并[ d ]噻吩并[ b，˚F ] borepins作为一类新建立用于通过以下结构特征动机功能材料块组成：（1）二噻吩的化学稳定性高[ b，˚Fborepin物种；（2）具有孔销环的高共轭四环体系；（3）通过在苯环上引入官能团而易于调节的电子结构。所制得的销钉在空气中无论在溶液中还是固体中都是稳定的，可以通过改变苯环上的取代基来微调电子状态。有趣的是，DFT计算表明，LUMO和LUMO + 1的能级受苯并[ d ]环的强烈影响，这取决于稠合噻吩环上硼桥联的位置。NICS和HOMA方法证明，苯并[ d ]二噻吩并[ b，fborepin系统相对较小。我们还报告了首次在硼销化合物中观察到固态的苯并[ d ] dithieno [ b，f ]硼氢化萘的意外红色发射。
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