Acta Chim. Sinica ›› 2015, Vol. 73 ›› Issue (11): 1147-1152.DOI: 10.6023/A15070447 Previous Articles     Next Articles



韩莹, 孟征, 陈传峰   

  1. 中国科学院化学研究所 分子识别与功能院重点实验室 北京 100190
  • 投稿日期:2015-07-03 发布日期:2015-11-19
  • 通讯作者: 陈传峰
  • 基金资助:

    项目受国家自然科学基金(Nos. 21332008, 91127009, 51373180)与科技部973项目(No. 2011CB932501)资助.

Complexation of Triptycene-Derived Macrotricyclic Host with π-Extended Viologens

Han Ying, Meng Zheng, Chen Chuanfeng   

  1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190
  • Received:2015-07-03 Published:2015-11-19
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21332008, 91127009, and 51373180), and the National Basic Research Program (No. 2011CB932501).

Development of novel macrocyclic hosts with the capability of binding selected substrates in specific complexation modes is always a very important and attractive topic in host-guest chemistry. Recently, we reported a novel macrotricyclic polyether containing two triptycene skeletons with rigid structure and two dibenzo-30-crown-10 moieties, which could show wide complexation abilities toward different kinds of guests. It was found that depending on the guests with different terminal functional groups and structures, the macrotricyclic polyether could form 1:1 or 1:2 complexes with the guests in different complexation modes in solution and also in the solid state. Moreover, the conformation of the macrocycle could easily be adjusted by the different encapsulated guests, which was to some extent similar to substrate induced fit of enzymes. It was also known that viologens with reversible single electron-accepting ability were usually used for the basic study of electrochemical and photoelectrochemical processes. They have also been widely utilized as electron deficient guests for host-guest chemistry. Compared with the viologens, π-extended viologens with conjugated structures have much more rich redox behaviors, and they could be used for photolithography, a source of electric oscillations, molecular electronic devices, and also as agents for charge transport across vesicles. However, the applications of π-extended viologens as guests in host-guest chemistry are still very limited. In this paper, complexation between the triptycene-derived macrotricyclic host and π-extended viologens in both solution and solid state was investigated in detail. It was found that depending on the guests with different linker-species and terminal functional groups, the macrotricyclic host could form 1:1 or 1:2 complexes with the guests in solution. Besides the 1:1 or 1:2 complexes, the macrotricyclic host could also form supramolecular poly[3]pseudorotaxane-type complexes with the guests in different complexation modes in the solid state. Formation of the complexes was proved by the 1H NMR, ESI-MS spectra, and X-ray crystal structures.

Key words: triptycene, macrotricyclic host, complexation, π-extended viologen