Citation: LI Ying-Ruo, ZHANG Hong-Tao, QI Chuan-Min, GUO Xue-Feng. New Spiropyran Derivatives: Ion Sensing and Information Processing at the Molecular Level[J]. Acta Physico-Chimica Sinica, ;2012, 28(10): 2471-2479. doi: 10.3866/PKU.WHXB201205155 shu

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

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 Date: 31 March 2012
Available Online: 15 May 2012
Fund Project: 国家重点基础研究发展规划项目(973) (2009CB623703, 2012CB921404) (973) (2009CB623703, 2012CB921404) 国家自然科学基金(20833001, 51121091, 2112016, 21071022) (20833001, 51121091, 2112016, 21071022)全国高等学校优秀博士论文作者专项基金(2007B21)资助 (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 od 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.
- Spiropyran,
- Chemical sensor,
- Logic gate,
- UV-Vis absorption spectrum,
- Fluorescence spectrum
1. [1]
  
  (1) Irie, M. Chem. Rev. 2000, 100, 1685. doi: 10.1021/cr980069d
2. [2]
  (2) Irie, M.; Fukaminato, T.; Sasaki, T.; Tamai, N.; Kawai, T. Nature2002, 420, 759. doi: 10.1038/420759a
3. [3]
  (3) de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley,A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515. doi: 10.1021/cr960386p
4. [4]
  (4) Kocer, A.;Walko, M.; Meijberg,W.; Feringa, B. L. Science2005, 309, 755. doi: 10.1126/science.1114760
5. [5]
  (5) Berkovic, G.; Krongauz, V.;Weiss, V. Chem. Rev. 2000, 100,1741. doi: 10.1021/cr9800715
6. [6]
  (6) Guo, X.; Zhang, D.; Zhu, D. Adv. Mater. 2004, 16, 125. doi: 10.1002/adma.200306102
7. [7]
  (7) Kawata, S.; Kawata, Y. Chem. Rev. 2000, 100, 1777. doi: 10.1021/cr980073p
8. [8]
  (8) Delaire, J. A.; Nakatani, K. Chem. Rev. 2000, 100, 1817. doi: 10.1021/cr980078m
9. [9]
  (9) Tamai, N.; Miyasaka, H. Chem. Rev. 2000, 100, 1875. doi: 10.1021/cr9800816
10. [10]
  (10) Guo, X.; Zhang, D.; Yu, G.;Wan, M.; Li, J.; Liu, Y.; Zhu, D.Adv. Mater. 2004, 16, 636. doi: 10.1002/adma.200305792
11. [11]
  (11) Shen, Q.;Wang, L.; Liu, S.; Cao, Y.; Gan, L.; Guo, X.;Steigerwald, M. L.; Shuai, Z.; Liu, Z.; Nuckolls, C. Adv. Mater.2010, 22, 3282. doi: 10.1002/adma.201000471
12. [12]
  (12) Guo, X.; Huang, L.; O'Brien, S.; Kim, P.; Nuckolls, C. J. Am. Chem. Soc. 2005, 127, 15045. doi: 10.1021/ja054335y
13. [13]
  (13) Lee, H. Y.; Diehn, K. K.; Sun, K.; Chen, T.; Raghavan, S. R.J. Am. Chem. Soc. 2011, 133, 8461. doi: 10.1021/ja202412z
14. [14]
  (14) Vlassiouk, I.; Park, C. D.; Vail, S. A.; Gust, D.; Smirnov, S.Nano Lett. 2006, 6, 1013. doi: 10.1021/nl060313d
15. [15]
  (15) Guo, X.; Zhang, D.; Tao, H.; Zhu, D. Org. Lett. 2004, 6, 2491.doi: 10.1021/ol0494111
16. [16]
  (16) Zhang, H.; Guo, X.; Hui, J.; Hu, S.; Xu,W.; Zhu, D. Nano Lett.2011, 11, 4939. doi: 10.1021/nl2028798
17. [17]
  (17) Jiang, G.; Song, Y.; Guo, X.; Zhang, D.; Zhu, D. Adv. Mater.2008, 20, 2888. doi: 10.1002/adma.200800666
18. [18]
  (18) Shao, N.; Zhang, Y.; Cheung, S.; Yang, R.; Chan,W.; Mo, T.; Li,K.; Liu, F. Anal. Chem. 2005, 77, 7294. doi: 10.1021/ac051010r
19. [19]
  (19) Sakamoto, H.; Takagaki, H.; Nakamura, M.; Kimura, K. Anal. Chem. 2005, 77, 1999. doi: 10.1021/ac048642i
20. [20]
  (20) Inouye, M.; Akamatsu, K.; Nakazumi, H. J. Am. Chem. Soc.1997, 119, 9160. doi: 10.1021/ja9707668
21. [21]
  (21) Shiraishi, Y.; Adachi, K.; Itoh, M.; Hirai, T. Org. Lett. 2009, 11,3482. doi: 10.1021/ol901399a
22. [22]
  (22) Takase, M.; Inouye, M. Chem. Commun. 2001, 2432.
23. [23]
  (23) Shao, N.; Jin, J. Y.; Cheung, S. M.; Yang, R. H.; Chan,W. H.;Mo, T. Angew. Chem. Int. Edit. 2006, 45, 4944. doi: 10.1002/anie.200600112
24. [24]
  (24) Andersson, J.; Li, S.; Lincoln, P.; Andréasson, J. J. Am. Chem. Soc. 2008, 130, 11836. doi: 10.1021/ja801968f
25. [25]
  (25) de Silva, A. P.; Gunaratne, H. Q. N.; McCoy, C. P. Nature 1993,364, 42. doi: 10.1038/364042a0
26. [26]
  (26) de Silva, A. P.; Gunaratne, H. Q. N.; McCoy, C. P. J. Am. Chem. Soc. 1997, 119, 7891. doi: 10.1021/ja9712229
27. [27]
  (27) de Silva, A. P.; McClenaghan, N. D. J. Am. Chem. Soc. 2000,122, 3965. doi: 10.1021/ja994080m
28. [28]
  (28) Guo, X.; Zhang, D.; Zhou, Y.; Zhu, D. J. Org. Chem. 2003, 68,5681. doi: 10.1021/jo034243w
29. [29]
  (29) Raymo, F. M. Adv. Mater. 2002, 14, 401. doi: 10.1002/1521-4095(20020318)14:6<401::AID-ADMA401>3.0.CO;2-F
30. [30]
  (30) Guo, X.; Zhang, D.; Zhang, G.; Zhu, D. J. Phys. Chem. B. 2004,108, 11942. doi: 10.1021/jp047706q
31. [31]
  (31) Guo, X.; Zhang, D.;Wang, T.; Zhu, D. Chem. Commun. 2003,914.
32. [32]
  (32) Raymo, F. M.; Giordani, S. J. Am. Chem. Soc. 2001, 123, 4651.doi: 10.1021/ja005699n
33. [33]
  (33) Hirano, M.; Osakada, K.; Nohira, H.; Miyashita, A. J. Org. Chem. 2001, 67, 533.
34. [34]
  (34) Guo, X.; Zhou, Y.; Zhang, D.; Yin, B.; Liu, Z.; Liu, C.; Lu, Z.;Huang, Y.; Zhu, D. J. Org. Chem. 2004, 69, 8924. doi: 10.1021/jo0487799
35. [35]
  (35) Shao, N.; Jin, J.;Wang, H.; Zheng, J.; Yang, R.; Chan,W.;Abliz, Z. J. Am. Chem. Soc. 2009, 132, 725.
36. [36]
  (36) Natali, M.; Soldi, L.; Giordani, S. Tetrahedron 2010, 66, 7612.doi: 10.1016/j.tet.2010.07.035
37. [37]
  (37) Fries, K. H.; Driskell, J. D.; Samanta, S.; Locklin, J. Anal. Chem. 2010, 82, 3306. doi: 10.1021/ac1001004
38. [38]
  (38) Paramonov, S. V.; Lokshin, V.; Fedorova, O. A. J. Photochem. Photobiol. C: Photochem. Rev. 2011, 12, 209. doi: 10.1016/j.jphotochemrev.2011.09.001
39. [39]
  (39) Poonia, N. S.; Bajaj, A. V. Chem. Rev. 1979, 79, 389. doi: 10.1021/cr60321a002
40. [40]
  (40) Abdullah, A.; Roxburgh, C. J.; Sammes, P. G. Dyes and Pigments 2008, 76, 319. doi: 10.1016/j.dyepig.2006.09.002
41. [41]
  (41) Ipe, B. I.; Mahima, S.; Thomas, K. G. J. Am. Chem. Soc. 2003,125, 7174. doi: 10.1021/ja0341182
42. [42]
  (42) Nolan, E. M.; Lippard, S. J. Accounts Chem. Res. 2008, 42, 193.
43. [43]
  (43) Huang, S.; Clark, R. J.; Zhu, L. Org. Lett. 2007, 9, 4999. doi: 10.1021/ol702208y
44. [44]
  (44) Kowalczyk, T.; Lin, Z.; Voorhis, T. V. J. Phys. Chem. A 2010,114, 10427.
45. [45]
  (45) Winkler, J. D.; Bowen, C. M.; Michelet, V. J. Am. Chem. Soc.1998, 120, 3237. doi: 10.1021/ja974181p
46. [46]
  (46) Zhao, J.; Nelson, D. J. J. Inorg. Biochem. 2005, 99, 383. doi: 10.1016/j.jinorgbio.2004.10.005
47. [47]
  (47) Torrado, A.;Walkup, G. K.; Imperiali, B. J. Am. Chem. Soc.1998, 120, 609. doi: 10.1021/ja973357k
48. [48]
  (48) Saghatelian, A.; Völcker, N. H.; Guckian, K. M.; Lin, V. S. Y.;Ghadiri, M. R. J. Am. Chem. Soc. 2002, 125, 346.
49. [49]
  (49) Qu, D. H.; Ji, F. Y.;Wang, Q. C.; Tian, H. Adv. Mater. 2006, 18,2035. doi: 10.1002/adma.200600235
50. [50]
  (50) de Sousa, M.; Kluciar, M.; Abad, S.; Miranda, M. A.; de Castro,B.; Pischel, U. Photochem. Photobiol. Sci. 2004, 3, 639. doi: 10.1039/b406415a
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