MAPEX Center for Materials and Processes, University of Bremen, Bibliothek Str. 1, 28359 Bremen, Germany.
Institute for Organic and Analytical Chemistry, University of Bremen, Leobener Str. 7, 28359 Bremen, Germany.
Molecules. 2020 Oct 28;25(21):4993. doi: 10.3390/molecules25214993.
A new spirostannole, 1,1',3,3'-tetrakis(5-methylthiophen-2-yl)-4,4',5,5',6,6',7,7'-octahydro-2,2'-spirobi[benzo[]stannole] (), is synthesised and the molecular structure is compared with the optimised geometry from DFT calculations. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) are twice degenerated and show a small HOMO-LUMO energy gap of 3.2 eV. In addition, cyclic voltammetry measurements are conducted and three redox processes are observed. Absorption and emission spectra show maxima at λ 436 nm and λ 533 nm, respectively. Spirostannole is a strongly absorbing material, but an extremely weak emitter in solution at 295.15 K. However, when the solution is cooled from 280 to 80 K, the emission becomes visible. The reaction of spirostannole with methyllithium is monitored by NMR spectroscopy at 238.15 K. The Sn{H} NMR signal shifts from -36.0 () to -211.0 ppm, which is indicative of the formation of the lithium pentaorganostannate . The complex is thermally instable at 295.15 K, but insights into the molecular structure and electronic behaviour are obtained by DFT and TD-DFT calculations.
一种新的螺环二氢吲哚并[3,2-b]咔唑，1,1',3,3'-四（5-甲基噻吩-2-基）-4,4',5,5',6,6',7,7'-八氢-2,2'-螺[苯并[g]吲哚并[3,2-b]咔唑] ()，被合成出来，并与从 DFT 计算优化的几何结构进行了比较。最高占据分子轨道（HOMO）和最低未占据分子轨道（LUMO）是双重简并的，并且显示出 3.2 eV 的小 HOMO-LUMO 能隙。此外，还进行了循环伏安法测量，观察到了三个氧化还原过程。吸收和发射光谱分别在 λ 436 nm 和 λ 533 nm 处显示出最大值。螺环二氢吲哚并[3,2-b]咔唑是一种强吸收材料，但在 295.15 K 的溶液中是一种非常弱的发射体。然而，当溶液从 280 冷却到 80 K 时，发射变得可见。螺环二氢吲哚并[3,2-b]咔唑与甲基锂的反应在 238.15 K 下通过 NMR 光谱进行监测。Sn{H} NMR 信号从-36.0 () 位移到-211.0 ppm，这表明形成了五有机锡酸钠。该配合物在 295.15 K 时热不稳定，但通过 DFT 和 TD-DFT 计算可以获得对分子结构和电子行为的深入了解。
