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首页> 外文期刊>Chemistry: A European journal >Ultrafast Charge-Separation in Triphenylamine-BODIPY-Derived Triads Carrying Centrally Positioned, Highly Electron-Deficient, Dicyanoquinodimethane or Tetracyanobutadiene Electron-Acceptors
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Ultrafast Charge-Separation in Triphenylamine-BODIPY-Derived Triads Carrying Centrally Positioned, Highly Electron-Deficient, Dicyanoquinodimethane or Tetracyanobutadiene Electron-Acceptors

机译：超快电荷分离在三苯胺 - Bodipy衍生的三合会中携带中央定位，高电子缺乏，二氰基二甲烷或四环丁二烯电子对准

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摘要

A series of new triphenylamine (TPA)-substituted BODIPYs 1-3 have been designed and synthesized through the Pd-catalysed Sonogashira cross-coupling and [2+2] cycloaddition-retroelectrocyclization reactions in good yields. This procedure yielded highly electron-deficient tetracyanobutadiene (TCBD) or dicyanoquinodimethane (DCNQ) electron-acceptor units centrally located at the TPA-BODIPY system. As a consequence, significant perturbation of the photonic and electronic properties was observed. The triads 2 and 3 showed red-shifted absorption, in addition to a strong charge-transfer-type absorption in the case of 3. The electrochemical studies revealed multi-redox processes involving the TPA, TCBD or DCNQ and BODIPY entities. The computational studies were performed at the B3LYP/6-31G** level to elucidate the geometry and electronic structures. An energy level diagram established for triads 2 and 3 revealed that the photoinduced charge-separation from the 1BODIPY* is thermodynamically possible. In addition, charge transfer from TPA to TCBD in 2 and DCNQ in 3 was also possible. These charge transfer mechanisms were confirmed by photochemical studies performed using time-resolved emission and femtosecond-transient-absorption studies in solvents of varying polarity. Ultrafast charge-separation has been witnessed in these closely spaced, strongly interacting triads. The charge-separated state returned to the ground state without populating the 3BODIPY*.
机译：通过PD催化的Sonogashira交叉偶联和[2 + 2]环形加法 - 循环反应，一系列新的三苯胺（TPA） - 取出的BODIPYS 1-3已经设计和合成了良好的产量。该方法产生高电子缺陷的四环丁二烯（TCBD）或二氰基二甲烷（DCNQ）电子 - 受体单元位于TPA-Bodipy系统中。因此，观察到光子和电子性质的显着扰动。三合组2和3显示出红移吸收，除了3的情况下的强电荷转移型吸收外，电化学研究揭示了涉及TPA，TCBD或DCNQ和Bodipy实体的多氧化还原过程。在B3LYP / 6-31G **水平下进行计算研究以阐明几何形状和电子结构。为三联器2和3建立的能量水平图揭示了从1Bodipy *的光引起的电荷分离是可以热力学上的。此外，在2和DCNQ中，从TPA到TCBD的电荷转移也是可能的。通过使用不同极性溶剂的溶剂中的时间分辨发射和飞秒 - 瞬态吸收研究进行光化学研究证实了这些电荷转移机制。在这些紧密间隔的强烈相互作用的三合会中，超快充电分离已经见证。电荷分离状态返回到地状态而不填充3Bodipy *。

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