Chem. J. Chinese Universities ›› 2010, Vol. 31 ›› Issue (7): 1353.

• Articles • Previous Articles     Next Articles

Synthesis and Complexation Studies in Solution of Novel Diacetylene-diimide Cyclophanes

ZHOU Song-Gen, CHEN Mu-Juan, TANG Ming-Fei, JIANG La-Sheng*, XU Zhi-Kai, ZHANG Su-Hui, LIANG Ji-Dong   

  1. School of Chemistry and Environment, South China Normal University, Guangzhou 510006, China
  • Received:2009-10-23 Online:2010-07-10 Published:2010-07-10
  • Contact: JIANG La-Sheng. E-mail: jianglsh@scnu.edu.cn
  • Supported by:

    国家自然科学基金(批准号: 20672038)和广东省自然科学基金(批准号: 8151063101000015)资助.

Abstract:

Two new cyclophanes(3a, 3b) containing an aromatic diimide unit and a diacetylene unit were synthesized via alkylation reaction, Mitsunobu reaction, Eglinton coupling reaction in satisfactory total yield. Their structures were confirmed by NMR, ESI-MS, and elemental analysis or HRMS. Their complexation behavior in solution with TTF or DNP was investigated by means of 1H NMR experiment in acetone-d6 and UV experiment in CHCl3. The chemical shift of protons of the cyclophanes and the UV absorption spectra were changed with the addition of TTF/DNP guests. The association constants of 3a/DNP and 3b/DNP are determined to be 20 and 24 L/mol, respectively, while the association constants of 3a/TTF and 3b/TTF are very small. These results indicate that these new cyclophanes can form complexes with TTF or DNP in solution, implying that they may be useful for constructing interlocked structures such as rotaxanes and catenanes.

Key words: Cyclophane; Pyromellitic diimide; Diacetylene; Host-guest interaction

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