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Colorimetric recognition using functional phenolphthalein derivatives

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Abstract

Three types of host molecules 1–3 based on a phenolphthalein (one of the most popular pH indicators) and two crown ethers were prepared for use in colorimetric recognition of linear diamines, triamines, sequence of non-protected dipeptides in methanol or water solution.

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Fig. 1
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Notes

  1. In Fig. 9, the proposed colored complex between host 1 and guest 13 is shown as canonical structure. Therefore, there may be some irrational interaction between the quinoid form of the phenolic crown ether of the host and the neutral amino group of the guest. We can interpret the actual complex as follows: (i) the guest amine reacts with free host 1 to generate two kinds of dianions, (ii) with regard to “colored” complex, one anion preferentially locates on the carboxylate, and another anion spreads over the two phenolic rings, and (iii) one proton is exchanged between the corresponding two amines through surrounding methanol, and thus both amines acquire a cationic character (No coloration was observed in a protic polar solvents, such as CHCl3, DMSO, and DMF, see Fig. 16).

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Acknowledgments

The author thanks all collaborators mentioned in the references. He especially thanks Prof. Kaoru Fuji and Prof. Takeo Kawabata for their suggestions and discussions, Dr. Daisuke Tanima, Dr. Tomokazu Kusumoto, Dr. Mohammad Nuruzzaman, Mr. Noriyuki Hayashi, and Ms. Yoko Imamura for their great contributions to this work. This study was partly supported by Grants-in-Aid for Scientific Research (Nos. 14572003 and 18390003) from the Ministry of Education, Culture, Sports, Science and Technology of Japan, and Foundation for Pharmaceutical Sciences, Japan. He also thanks Prof. Norihiro Tokitoh and Prof. Takahiro Sasamori (Kyoto Univ.) for performing the X-ray structural analysis, and Prof. Yasuhisa Kuroda (Kyoto Institute of Technology), Prof. Keiji Hirose and Prof. Yoshito Tobe (Osaka Univ.) for gifts of software for determination of binding constants. This is a paper selected for “HGCS Japan Award of Excellence 2007”.

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  1. Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto, 611-0011, Japan

    Kazunori Tsubaki

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Tsubaki, K. Colorimetric recognition using functional phenolphthalein derivatives. J Incl Phenom Macrocycl Chem 61, 217–225 (2008). https://doi.org/10.1007/s10847-008-9419-3

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