Photoinduced charge transfer and electrochemical properties of triphenylamine I(h)-Sc3N@C80 donor-acceptor conjugates.
Photoinduced charge transfer and electrochemical properties of triphenylamine I(h)-Sc3N@C80 donor-acceptor conjugates.
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DOI：
10.1021/ja900612g
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发表时间：
2009-06-10
影响因子：
15
通讯作者：
Echegoyen L
中科院分区：
文献类型：
--
作者：
Pinzón JR;Gasca DC;Sankaranarayanan SG;Bottari G;Torres T;Guldi DM;Echegoyen L
合成了两种以三苯胺(TPA)为供体体系的异构体[5，6]-吡咯烷-iH-Sc3N@C80电子供体受体共轭化合物。对新化合物进行了电化学和光物理研究，并与它们的C60类似物进行了比较，以确定给电子体体系的连接位置(N-取代和2-取代吡咯烷)在光致电荷分离态形成中的作用，II)对逆环加成反应的热稳定性，以及III)改变C60作为电子受体的作用。研究发现，当给电子体连接到吡咯烷氮原子上时，所得到的二元体产生的自由基对比相应的C60和iH-Sc3N@C80二元体的2-取代异构体都要长得多。此外，N-取代TPA-1H-Sc3N@C80的热稳定性远好于2-取代的TPA-1H-Sc3N@C80。最后，iH-Sc3N@C80的电荷分离态比它们的C60类似物具有更长的电荷分离态，从而证实了用iH-Sc3N@C80代替C60作为受体构建富勒烯基受体共轭化合物的优势。这些发现对于iH-Sc3N@C80作为塑料有机太阳能电池材料的设计和未来的应用具有重要的意义。
Two isomeric [5,6]-pyrrolidine-Ih-Sc3N@C80 electron donor acceptor conjugates containing triphenylamine (TPA) as the donor system were synthesized. Electrochemical and photophysical studies of the novel conjugates were made and compared with those of their C60 analogues, in order to determine i) the effect of the linkage position (N-substituted versus 2-substituted pyrrolidine) of the donor system in the formation of photoinduced charge separated states, ii) the thermal stability towards the retro-cycloaddition reaction and iii) the effect of changing C60 for Ih-Sc3N@C80 as the electron acceptor. It was found that when the donor is connected to the pyrrolidine nitrogen atom, the resulting dyad produces a significantly longer lived radical pair than the corresponding 2-substituted isomer for both the C60 and Ih-Sc3N@C80 dyads. In addition to that, the N-substituted TPA-Ih-Sc3N@C80 dyad has much better thermal stability than the 2-subtituted one. Finally, the Ih-Sc3N@C80 dyads have considerably longer lived charge separated states than their C60 analogues, thus approving the advantage of using Ih-Sc3N@C80 instead of C60 as the acceptor for the construction of fullerene based donor acceptor conjugates. These findings are important for the design and future application of Ih-Sc3N@C80 dyads as materials for the construction of plastic organic solar cells.
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