Acta Phys. -Chim. Sin. ›› 2012, Vol. 28 ›› Issue (10): 2471-2479.doi: 10.3866/PKU.WHXB201205155

• PHYSICAL CHEMISTRY OF MATERIALS • Previous Articles     Next Articles

New Spiropyran Derivatives: Ion Sensing and Information Processing at the Molecular Level

LI Ying-Ruo1, ZHANG Hong-Tao2, QI Chuan-Min1, GUO Xue-Feng2,3   

  1. 1. Key Laboratory of Radiopharmaceuticals, Department of Chemistry, Beijing Normal University, Beijing 100875, P. R. China;
    2. Beijing National Laboratory for Molecular Sciences, State Key Laboratory for Structural Chemistry of Unstable and Stable Species, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, P. R. China;
    3. Department of Advanced Materials and Nanotechnology, College of Engineering, Peking University, Beijing 100871, P. R. China
  • Received:2012-03-31 Revised:2012-05-14 Published:2012-09-26
  • Contact: QI Chuan-Min, GUO Xue-Feng;
  • Supported by:

    The project was supported by the National Key Basic Research Program of China (973) (2009CB623703, 2012CB921404), National Natural Science Foundation of China (20833001, 51121091, 2112016, 21071022), and Foundation for the Author of National Excellent Doctoral Dissertation of Higher Education, China (2007B21).


We have designed and synthesized a new class of spiropyran derivatives (SP1-SP4) with functional chelating groups, such as pyridine or quinoline moieties and a methoxy group (―OMe), for use in metal ion sensing and information processing at the molecular level. It is notable that metal ions can favor coordination with chelating groups and facilitate the photoisomerization of spiropyran molecules from the closed form to the open merocyanine form without UV irradiation, thus leading to significant changes in their chemical and physical properties. UV-Vis absorption studies indicated that SP2 and SP4 exhibited metal ion-dependent reversible binding affinities that result in different hypsochromic shifts for the MC-Mn+ complexes. These changes in color can be recognized by eye, thus offering an easy colorimetric method for metal ion detection. Further emission studies distinguished them as promising candidates for Zn2+ detection with good sensitivity and selectivity. Moreover, on the basis of their absorption and fluorescence spectra, several combinational logic gates were constructed for information processing at the molecular level. These results demonstrate that spiropyran derivatives with desired functionalities show great potential not only for chemical or environmental sensors, but also for future molecular computing.

Key words: Spiropyran, Chemical sensor, Logic gate, UV-Vis absorption spectrum, Fluorescence spectrum