Helicenes[1], a class of molecules that consist of ortho-fused aromatic rings with helical chirality, have attracted great interest owing to their unique structural features and wide potential applications in materials science, molecular recognition, and asymmetric synthesis. In recent years, we are interested in the synthesis and applications of helicene derivatives. Consequently, we have developed a new method for the synthesis of helicene derivatives, and explored their potential applications in mechanochemistry and molecular assembly[2]. We also developed a new kind organic imide dyes based on helicene or hydrohelicene skeleton, and found that they had wide potential applications in fluorescence sensing, biological imaging, and optical waveguides[3]. Unexpectedly, we also found that helicene diols could undergo transannular dearomatization triggered by dioxygen to give diones in quantitative yields within several minutes. By virtue of this, the chirality was successfully transferred from helicity to centeral chirality to form distorted pi-extended diones with two all-carbon quaternary stereocenters[4].
References [1] Y. Shen, C.-F. Chen, Chem. Rev., 2012, 112, 1463. [2] J.-D. Chen, H.-Y. Lu, C.-F. Chen, Chem. Eur. J., 2010, 16, 11843. [3] (a) M. Li, Y. Niu, X. Zhu, Q. Peng, H.-Y. Lu, A. Xia, C.-F. Chen, Chem. Commun. 2014, 50, 2993; (b) M. Li, L.-H. Feng, H.-Y. Lu, S. Wang, C.-F. Chen, Adv. Funct. Mater. 2014, 24, 4405; (c) Y.-Y. Li, H.-Y. Lu, M. Li, X.-J. Li, C.-F. Chen, J. Org. Chem. 2014, 79, 2139. (d) M. Li, W. Yao, J.-D. Chen, H.-Y. Lu, Y. Zhao, C.-F. Chen, J. Mater. Chem. C 2014, 2, 8373. [4] Y. Shen, H.-Y. Lu, C.-F. Chen, Angew. Chem., Int. Ed. 2014, 53, 4648.