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首页> 外文期刊>Chemistry: A European journal >Electron donor-acceptor interactions in regioselectively synthesized exTTF_2-C_(70)(CF_3)_(10) dyads
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Electron donor-acceptor interactions in regioselectively synthesized exTTF_2-C_(70)(CF_3)_(10) dyads

机译：区域选择性合成的exTTF_2-C_（70）（CF_3）_（10）二联体中的电子供体-受体相互作用

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摘要

The decakis(trifluoromethyl)fullerene C_1-C_(70)O(CF _3)_(10) in which the CF_3 groups are arranged on a para~7-meta-para ribbon of C_6(CF_3)_2 edge-sharing hexagons, and which has now been prepared in quantities of hundreds of milligrams, was reacted under standard Bingel-Hirsch conditions with a bis-π-extended tetrathiafulvalene (exTTF) malonate derivative to afford a single cxTTF_2-C_(70)(CF_3)_(10) regioisomer in 80% yield based on consumed starting material. The highly soluble hybrid was thoroughly characterized by using ID ~1H, _(13)C, and ~(19)F NMR, 2D NMR, and UV/Vis spectroscopy; matrix-assisted laser desorption ionization (MALDI) mass spectrometry; and electrochemistry. The cyclic voltammogram of the exTTF_2C_(70)(CF_3) ~(10) dyad revealed an irreversible second reduction process, which is indicative of a typical retro-Bingel reaction; whereas the usual phenomenon of exTTF inverted potentials (E~1_(ox)>E~2_(ox)), resulting in a single, two-electron oxidation process, was also observed. Steady-state and time-resolved photolytic techniques demonstrated that the C_1-C_(70)(CF_3)_(10)singlet excited state is subject to a rapid electron-transfer quenching. The resulting charge-separated states were identified by transient absorption spectroscopy, and radical pair lifetimes of the order of 300 ps in toluene were determined. The exTTF_2C_(70)(CF_3)_(10), dyad represents the first example of exploitation of the highly soluble trifluoromethylated fullerenes for the construction of systems able to mimic the photosynthetic process, and is therefore of interest in the search for new materials for photovoltaic applications.
机译：十（三氟甲基）富勒烯C_1-C_（70）O（CF_3）_（10），其中CF_3基团排列在C_6（CF_3）_2边共享六边形的对〜7-对-对带上，在标准Bingel-Hirsch条件下，将已制备数百毫克的水与双π扩展的四硫富瓦烯（exTTF）丙二酸酯衍生物进行反应，得到单一的cxTTF_2-C_（70）（CF_3）_（10）区域异构体，基于消耗的原料，产率为80％。通过使用〜1H，_（13）C和〜（19）F NMR，2D NMR和UV / Vis光谱对高溶解性杂化物进行了彻底表征。基质辅助激光解吸电离（MALDI）质谱;和电化学。 exTTF_2C_（70）（CF_3）〜（10）dyad的循环伏安图显示了不可逆的第二还原过程，这表明典型的逆向Bingel反应。而通常观察到的exTTF反向电势现象（E〜1_（ox）> E〜2_（ox）），导致一个单电子氧化过程。稳态和时间分辨光解技术表明，C_1-C_（70）（CF_3）_（10）单重激发态会经历快速的电子转移猝灭。通过瞬态吸收光谱法鉴定得到的电荷分离状态，并确定了在甲苯中约300ps的自由基对寿命。 exTTF_2C_（70）（CF_3）_（10）dyad是利用高可溶性三氟甲基化富勒烯构建能够模拟光合作用过程的系统的第一个实例，因此在寻找用于光伏应用。

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