Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555 Japan.
Chemistry. 2010 Jul 5;16(25):7554-62. doi: 10.1002/chem.201000373.
A novel trifluoroethoxy (TFEO)-coated SubPc (1) and various axially functionalised derivatives thereof (2) have been efficiently synthesised. The advantage of the TFEO-coating on SubPcs compared to conventional fluorine-coated or uncoated molecules has been clearly demonstrated, as axial derivatisation has been realised in very good yields. Among various SubPcs synthesised, formyl-SubPc 2f has been further used as a building block for the synthesis of donor-acceptor SubPc-C(60) hybrid 8, while iodo-SubPc 2e has been used for the synthesis of trifluoroethoxy-coated SubPc-Pc dyads 9 and 10. All of these compounds are highly soluble in all common organic solvents, which greatly facilitates their purification and characterisation. The SubPcs 2a-c incorporating oligoethylene glycol moieties are attractive from a biological point of view, while SubPcs 8-10 may prove useful for studies of intramolecular electron- and energy-transfer processes.
一种新型三氟乙氧基（TFEO）涂层的 SubPc（1）和各种轴向官能化的衍生物（2）已被高效合成。与传统的氟涂层或未涂层分子相比，SubPc 上的 TFEO 涂层具有明显的优势，因为轴向衍生化以非常好的产率实现了。在所合成的各种 SubPc 中，甲酰基-SubPc 2f 进一步用作合成给体-受体 SubPc-C(60) 杂化物 8 的构建块，而碘代-SubPc 2e 则用于合成三氟乙氧基涂层的 SubPc-Pc 二聚体 9 和 10。所有这些化合物在所有常见有机溶剂中都具有很高的溶解度，这极大地促进了它们的纯化和表征。从生物学的角度来看，含有聚乙二醇部分的 SubPc 2a-c 很有吸引力，而 SubPc 8-10 可能有助于研究分子内电子和能量转移过程。
