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Simply Structured Conjugated Compounds with Cyanoacrylate or Acrylonitrile Groups for Sensing of p-Toluenethiol

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Abstract

Simply structured conjugated compounds with cyanoacrylate (CA 1–4) and acrylonitrile (AN 1–4) terminal groups were synthesized by a Knoevenagel condensation reaction in one step and investigated for their recognition properties to p-toluenethiol by UV-vis, fluorescence spectra, and FT-IR measurements. When p-toluenethiol was added to CA 1, the FT-IR spectra revealed a cleavage of alkene caused by the addition reaction between p-toluenethiol and CA 1. An increase in p-toluenethiol concentration, a blue-shifted absorption band, and a decrease in the fluorescence intensity of CA 1 were observed because of the decrease in its effective conjugated length. Therefore, the most simply structured CA 1 was found to be the most effective and the most sensitive chemical sensor for p-toluenethiol.

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References

  1. J. B. Schulz, J. Lindenau, J. Seyfriend, and J. Dichgans, Eur. J. Biochem., 2000, 267, 4904.

    Article  CAS  PubMed  Google Scholar 

  2. S. J. James, P. Cutler, S. Melnyk, S. Jernigan, L. Janak, D. W. Gaylor, and J. A. Neubrander, Am. J. Clin. Nutr., 2004, 80, 1611.

    Article  CAS  PubMed  Google Scholar 

  3. J. C. Love, L. A. Estroff, J. K. Kriebel, R. G. Nuzzo, and G. M. Whitesides, Chem. Rev., 2005, 105, 1103.

    Article  CAS  PubMed  Google Scholar 

  4. P. Morf, F. Raimondi, H. G. Nothofer, B. Schnyder, A. Yasuda, M. Wessels, and T. A. Jung, Langmuir, 2006, 22, 658.

    Article  CAS  PubMed  Google Scholar 

  5. L. A. Herzenberg, S. C. De Rosa, J. G. Dubs, M. Roederer, M. T. Anderson, S. W. Ela, S. C. Deresinski, and L. A. Herzenberg, Proc. Natl. Acad. Sci. U. S. A., 2009, 94, 1967.

    Article  Google Scholar 

  6. R. Hong, G. Han, J. M. Fernández, B. J. Kim, N. S. Forbes, and V. M. Rotello, J. Am. Chem. Soc., 2006, 128, 1078.

    Article  CAS  PubMed  Google Scholar 

  7. X. Chen, Y. Zhou, X. Peng, and J. Yoon, Chem. Soc. Rev., 2010, 39, 2120.

    Article  CAS  PubMed  Google Scholar 

  8. X. Yang, Y. Guo, and R. M. Strongin, Angew. Chem., Int. Ed., 2011, 50, 10690.

    Article  CAS  Google Scholar 

  9. X. Chen, S. K. Ko, M. J. Kim, I. Shin, and J. Yoon, Chem. Commun., 2010, 46, 2751.

    Article  CAS  Google Scholar 

  10. L. Deng, W. Wu, H. Guo, J. Zhao, S. Ji, X. Zhang, X. Yuan, and C. Zhang, J. Org. Chem., 2011, 76, 9294.

    Article  CAS  PubMed  Google Scholar 

  11. C. Yin, F. Huo, J. Zhang, R. Martínez-Máñez, Y. Yang, H. Lv, and S. Li, Chem. Soc. Rev., 2013, 42, 6032.

    Article  CAS  PubMed  Google Scholar 

  12. Y. Q. Sun, M. Chen, J. Liu, X. Lv, J. Li, and W. Guo, Chem. Commun., 2011, 47, 11029.

    Article  CAS  Google Scholar 

  13. I. M. Serafimova, M. A. Pufall, S. Krishnan, K. Duda, M. S. Cohen, R. L. Maglathlin, J. M. McFarland, R. M. Miller, M. Frödin, and J. Taunton, Nat. Chem. Biol., 2012, 8, 471.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. X. Sun, S. Yang, M. Guo, S. Ma, M. Zheng, and J. He, Anal. Sci., 2017, 33, 761.

    Article  CAS  PubMed  Google Scholar 

  15. Y. Yang, D. Zheng, Y. Xu, Q. Liu, C. Xu, Q. Jiao, and H. Zhu, Anal. Sci., 2018, 34, 1411.

    Article  CAS  PubMed  Google Scholar 

  16. T. A. Skotheim and J. Reynolds, “Handbook of Conducting Polymers”, 3rd ed., 2007, CRC Press, New York.

    Google Scholar 

  17. U. H. F. Bunz, Chem. Rev., 2000, 100, 1605.

    Article  CAS  PubMed  Google Scholar 

  18. D. T. McQuade, A. E. Pullen, and T. M. Swager, Chem. Rev., 2000, 100, 2537.

    Article  CAS  PubMed  Google Scholar 

  19. S. W. Thomas, G. D. Joly, and T. M. Swager, Chem. Rev., 2007, 107, 1339.

    Article  CAS  PubMed  Google Scholar 

  20. J. Kim, D. T. McQuade, S. K. McHugh, and T. M. Swager, Angew. Chem., Int. Ed., 2000, 39, 3868.

    Article  CAS  Google Scholar 

  21. C. Tan, E. Atas, J. G. Müller, M. R. Pinto, V. D. Kleiman, and K. S. Schanze, J. Am. Chem. Soc., 2004, 126, 13685.

    Article  CAS  PubMed  Google Scholar 

  22. J. Wang, H. Wang, S. Yang, H. Tian, Y. Liu, Y. Hao, J. Zhang, and B. Sun, Anal. Sci., 2018, 34, 329.

    Article  CAS  PubMed  Google Scholar 

  23. J. Xu, Z. Wang, C. Liu, Z. Xu, B. Zhu, N. Wang, K. Wang, and J. Wang, Anal. Sci., 2018, 34, 453.

    Article  CAS  PubMed  Google Scholar 

  24. H. Jia, C. Feng, and C. Tian, Anal. Sci., 2018, 34, 1079.

    Article  CAS  PubMed  Google Scholar 

  25. A. Y. Cho and K. Choi, Chem. Lett., 2012, 41, 1611.

    Article  CAS  Google Scholar 

  26. P. S. Rao and R. V. Venkataratnam, Tetrahedron Lett., 1991, 32, 5821.

    Article  CAS  Google Scholar 

  27. T. I. Reddy and R. S. Varma, Tetrahedron Lett., 1997, 38, 1721.

    Article  CAS  Google Scholar 

  28. I. Rodriguez, S. Iborra, A. Corma, F. Rey, and J. L. Jordá, Chem. Commun., 1999, 593.

    Google Scholar 

  29. J. S. Yadav, V. B. S. Reddy, A. K. Basak, B. Visali, A. V. Naraiah, and K. Nagaiah, Eur. J. Org. Chem., 2004, 546.

    Google Scholar 

  30. R. Das, D. Guha, S. Mitra, S. Kar, S. Lahiri, and S. Mukherjee, J. Phys. Chem. A, 1997, 101, 4042.

    Article  CAS  Google Scholar 

  31. A.-J. Attias, P. Hapiot, V. Wintgens, and P. Valet, Chem. Mater., 2000, 12, 461.

    Article  CAS  Google Scholar 

  32. F. J. Lange, M. Leuze, and M. Hanack, J. Phys. Org. Chem., 2001, 14, 474.

    Article  CAS  Google Scholar 

  33. B.-K. An, S.-K. Kwon, S.-D. Jung, and S. Y. Park, J. Am. Chem. Soc., 2002, 124, 14410.

    Article  CAS  PubMed  Google Scholar 

  34. C.-G. Dai, X.-J. Du, and Q.-H. Song, J. Org. Chem., 2015, 80, 12088.

    Article  CAS  PubMed  Google Scholar 

  35. Y.-L. Duan and Y.-S. Zheng, Talanta, 2013, 107, 332.

    Article  CAS  PubMed  Google Scholar 

  36. N. Adachi, M. Yoshinari, E. Suzuki, and M. Okada, J. Fluorescence, 2017, 27, 1449.

    Article  CAS  Google Scholar 

  37. H. S. Jung, X. Chen, J. S. Kim, and J. Yoon, Chem. Soc. Rev., 2013, 40, 6019.

    Article  Google Scholar 

Download references

Acknowledgments

This work was partially supported by the Research Institute for Science and Technology of Tokyo Denki University, Grant Number Q18K-04, Japan.

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Authors and Affiliations

  1. Division of Science, School of Science and Engineering, Tokyo Denki University, Hatoyama, Hiki, Saitama, 350-0394, Japan

    Naoya Adachi

  2. Department of Science and Engineering, Graduate School of Science and Engineering, Tokyo Denki University, Hatoyama, Hiki, Saitama, 350-0394, Japan

    Naoya Adachi & Eri Suzuki

Authors
  1. Naoya Adachi
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  2. Eri Suzuki
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Correspondence to Naoya Adachi.

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Adachi, N., Suzuki, E. Simply Structured Conjugated Compounds with Cyanoacrylate or Acrylonitrile Groups for Sensing of p-Toluenethiol. ANAL. SCI. 35, 745–750 (2019). https://doi.org/10.2116/analsci.18P569

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  • DOI: https://doi.org/10.2116/analsci.18P569

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