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Synthesis and photophysical properties of 2,2′-binaphthalene-based receptor bearing trimethylsilyl groups to improve the solubility

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Abstract

Two trimethylsilyl groups were introduced at 5- and 5′-positions of 2,2′-binaphthalene to improve the solubility of 2,2′-binaphthalene-based receptors. The X-ray crystallographic analysis revealed the twisted structure of 2 in the solid state. The solubility of 2 was moderately improved by 3.1-fold comparing with mother skeleton 1. As a practical example of 2, receptor 8 bearing two aza-15-crown-5 moieties was prepared and the selective binding of 8 with Ba2+ can be observed by the formation of sandwich-like complex, which shows no prevention of binding ability of the receptor by introduction of the bulky substituents.

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References

  1. Valeur, B., Leray, I.: Design principles of fluorescent molecular sensors for cation recognition. Coord. Chem. Rev. 205(1), 3–40 (2000)

    Article  CAS  Google Scholar 

  2. de Silva, A.P., Fox, D.B., Huxley, A.J.M., Moody, T.S.: Combining luminescence, coordination and electron transfer for signaling purposes. Coord. Chem. Rev. 205(1), 41–57 (2000)

    Article  Google Scholar 

  3. Geddes, C.D., Lakowicz, J.R.: Probe and Sensors for Cations: Small Molecule Sensing in Topics in Fluorescence Spectroscopy. Springer, New York (2005)

    Book  Google Scholar 

  4. Kondo, S., Nagamine, M., Yano, Y.: Synthesis and anion recognition properties of 8,8’-dithioureido-2,2’-binaphthalene. Tetrahedron Lett. 44(49), 8801–8804 (2003)

    Article  CAS  Google Scholar 

  5. Kondo, S., Kinjo, T., Yano, Y.: Synthesis of a novel intercalator based on 2,2’-binaphthalene bearing dimethylammonium groups. Bioorg. Med. Chem. Lett. 14(7), 1641–1643 (2004)

    Article  CAS  Google Scholar 

  6. Kondo, S., Kinjo, T., Yano, Y.: Barium ion sensing by a 2,2’-binaphthalene derivative bearing two monoaza-15-crown-5 ethers. Tetrahedron Lett. 46(18), 3183–3186 (2005)

    Article  CAS  Google Scholar 

  7. Kondo, S., Sato, M.: UV–Vis and fluorescence spectroscopic detection of anions by the conformational restriction of 2,2’-binaphthalene derivatives bearing thiourea groups through a methylene spacer. Tetrahedron 62(20), 4844–4850 (2006)

    Article  CAS  Google Scholar 

  8. Kondo, S.: Anion recognition by 2,2’-binaphthalene bearing imidazolium groups in MeCN. Supramol. Chem. 23(1&2), 29–36 (2011)

    Article  CAS  Google Scholar 

  9. Kondo, S., Nagamine, M., Karasawa, S., Ishihara, M., Unno, M., Yano, Y.: Anion recognition by 2,2’-binaphthalene derivatives bearing urea and thiourea groups at 8- and 8’-positions by UV–Vis and fluorescence spectroscopies. Tetrahedron 67(5), 943–950 (2011)

    Article  CAS  Google Scholar 

  10. Kondo, S., Sonoda, H., Katsu, T., Unno, M.: Improvement of solubility of 2,2’-binaphthalene derivatives bearing urea groups as anion receptors and their application to a chloride selective electrode. Sens. Actuators B 160(1), 684–690 (2011)

    Article  CAS  Google Scholar 

  11. Kondo, S., Takahashi, T., Takiguchi, Y., Unno, M.: Synthesis and photophysical properties of a 2,2’-bianthracene-based receptor bearing two aza-15-crown-5 ethers for naked-eye detection of barium ion. Tetrahedron Lett. 52(3), 453–457 (2011)

    Article  CAS  Google Scholar 

  12. Carpino, L.A., Wu, A.-C.: Solubilizing influence of 2,7-bis(trimethylsilyl) substitution on the fmoc residue. J. Org. Chem. 65(26), 9238–9240 (2000)

    Article  CAS  Google Scholar 

  13. Guo, L., Meng, F.S., Gong, X.D., Xiao, H.M., Chen, K.C., Tian, H.: Synthesis and spectral properties of soluble trimethylsilyl substituted metal-phthalocyanines. Dyes Pigment 49(2), 83–91 (2001)

    Article  CAS  Google Scholar 

  14. Chan, S.H., Lee, H.K., Wang, Y.M., Fu, N.Y., Chen, X.M., Cai, Z.W., Wong, H.N.C.: A soluble pentacene: synthesis, EPR and electrochemical studies of 2,3,9,10-tetrakis(trimethylsilyl)pentacene. Chem. Commun. 1, 66–68 (2005)

    Article  Google Scholar 

  15. Kyushin, S., Ikarugi, M., Goto, M., Hiratsuka, H., Matsumoto, H.: Synthesis and electronic properties of 9,10-disilylanthracenes. Organometallics 15(3), 1067–1070 (1996)

    Article  CAS  Google Scholar 

  16. Maeda, H., Inoue, Y., Ishida, H., Mizuno, K.: UV absorption and fluorescence properties of pyrene derivatives having trimethylsilyl, trimethylgermyl, and trimethylstannyl groups. Chem. Lett. 12, 1224–1225 (2001)

    Article  Google Scholar 

  17. Trotter, J.: The crystal and molecular structure of biphenyl. Acta Crystallogr. 14(11), 1135–1140 (1961)

    Article  CAS  Google Scholar 

  18. Hargraves, A., Hasan-Rizvi, S.: The crystal and molecular structure of biphenyl. Acta Crystallogr. 15(4), 365–373 (1962)

    Article  Google Scholar 

  19. Chen, M., Wu, G., Zhuang, S., Huang, Z., Qin, W., Wu, W.: Gaodeng Xuexiao Huaxue Xuebao 8, 556 (1987)

    CAS  Google Scholar 

  20. Nishio, M., Hirota, M., Umezawa, Y.: The CH–π Interaction: Evidence, Nature, and Consequences. Wiley-VCH, New York (1998)

    Google Scholar 

  21. An, H., Bradshaw, J.S., Izatt, R.M., Yan, Z.: Bis- and oligo(benzocrown ether)s. Chem. Rev. 94(4), 939–991 (1994)

    Article  CAS  Google Scholar 

  22. Fery-Forgues, S., Al-Ali, F.: Bis(azacrown ether) and bis(benzocrown ether) dyes: butterflies, tweezers and rods in cation binding. J. Photochem. Photobiol. C 5(2), 139–153 (2004)

    Article  CAS  Google Scholar 

  23. Geue, J.P., Head, N.J., Ward, A.D., Lincoln, S.F.: Complexation of alkali metal and alkaline earth ions by anthracene based fluorophores with one and two appended monoaza coronand receptors. Dalton Trans. 4, 521–526 (2003)

    Article  Google Scholar 

  24. Hayashita, T., Murakami, A., Teramae, N.: Potassium ion selective signaling based on intramolecular dimer formation of biscrown ether azochromophore. Chemosensor exhibiting forceps function. Chem. Lett. 33(5), 568–569 (2004)

    Article  CAS  Google Scholar 

  25. He, X., Lam, W.H., Zhu, N., Yam, V.W.-W.: Design and synthesis of calixarene-based bis-alkynyl-bridged dinuclear AuI isonitrile complexes as luminescent ion probes by the modulation of Au···Au interactions. Chem. Eur. J. 15(35), 8842–8851 (2009)

    Article  CAS  Google Scholar 

  26. Shimakoshi, H., Shibata, K., Hisaeda, Y.: Molecular recognition of redox-switchable bis-crown moieties assembled on a dicobalt complex. Inorg. Chem. 48(3), 1045–1052 (2009)

    Article  CAS  Google Scholar 

  27. Shao, M., Dongare, P., Dawe, L.N., Thompson, D.W., Zhao, Y.: Biscrown-annulated TTFAQ-dianthracene hybrid: synthesis, structure, and metal ion sensing. Org. Lett. 12(13), 3050–3053 (2010)

    Article  CAS  Google Scholar 

  28. Kubo, K., Sakurai, T.: Molecular recognition of pet fluoroionophores. Heterocycles 52(2), 945–976 (2000)

    Article  CAS  Google Scholar 

  29. de Silva, A.P., Moody, T.S., Wright, G.D.: Fluorescent PET (photoinduced electron transfer) sensors as potent analytical tools. Analyst 134(12), 2385–2393 (2009)

    Article  Google Scholar 

  30. Kim, J.H., Chang, S.-K.: Barium-selective chromoionophoric properties of nitro derivative of calix[4]arene-crown ethers. Bull. Korean Chem. Soc. 24(5), 674–676 (2003)

    Article  CAS  Google Scholar 

  31. Singh, A.K., Singh, R., Singh, R.P., Saxena, P.: Novel potentiometric sensor for monitoring barium(II) based on 2,3,4-pyridine-1,3,5,7,12-pentaazacyclopentadeca-3-ene. Sens. Actuators B 106(2), 779–783 (2005)

    Article  Google Scholar 

  32. Licchelli, M., Biroli, A.O., Poggi, A.: A prototype for the chemosensing of Ba2+ based on self-assembling fluorescence enhancement. Org. Lett. 8(5), 915–918 (2006)

    Article  CAS  Google Scholar 

  33. Zamani, H.A., Abedini-Torghabeh, J., Ganjali, M.R.: A highly selective and sensitive barium(II)-selective PVC membrane based on dimethyl 1-acetyl-8-oxo-2,8-dihydro- 1H-pyrazolo[5,1-a]isoindole-2,3-dicarboxylate. Electroanalysis 18(9), 888–893 (2006)

    Article  Google Scholar 

  34. McFarland, S.A., Finney, N.S.: Fluorescent chemosensors based on conformational restriction of a biaryl fluorophore. J. Am. Chem. Soc. 123(6), 1260–1261 (2001)

    Article  CAS  Google Scholar 

  35. McFarland, S.A., Finney, N.S.: Fluorescent signaling based on control of excited state dynamics. Biarylacetylene fluorescent chemosensors. J. Am. Chem. Soc. 124(7), 1178–1179 (2002)

    Article  CAS  Google Scholar 

  36. McFarland, S.A., Finney, N.S.: Modulating the efficiency of Ru(II) luminescence via ion binding-induced conformational restriction of bipyridyl ligands. Chem. Commun. 3, 388–389 (2003)

    Article  Google Scholar 

  37. Costero, A.M., Sanchis, J., Peransi, S., Gil, S., Sanz, V., Domench, A.: Bis(crown ethers) derived from biphenyl: extraction and electrochemical properties. Tetrahedron 60(21), 4683–4691 (2004)

    Article  CAS  Google Scholar 

  38. Costero, A.M., Gil, S., Sanchis, J., Sanz, S.P.V., Williams, J.A.G.: Conformationally regulated fluorescent sensors. Study of the selectivity in Zn2+ versus Cd2+ sensing. Tetrahedron 60(30), 6327–6334 (2004)

    Article  CAS  Google Scholar 

  39. Fang, A.G., Mello, J.V., Finney, N.S.: Structural studies of biarylpyridines fluorophores lead to the identification of promising long wavelength emitters for use in fluorescent chemosensors. Tetrahedron 60(49), 11075–11087 (2004)

    Article  CAS  Google Scholar 

  40. Horn, D.H.S., Warren, F.L.: Chloromethylation of 1- and 2-chloronaphthalenes. J. Chem. Soc. 144 (1946). doi:10.1039/JR9460000143

  41. Sheldrick, G.M.: SHELXS-97, Program for the Refinement of Crystal Structures. University of Göttingen, Germany (1997)

    Google Scholar 

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Acknowledgments

This work was supported in part by a Grant-in-Aid for Scientific Research (C) from Japan Society for the Promotion of Science, The Salt Science Research Foundation, Nos. 1006 and 1104, and a research grant from The Mazda Foundation.

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Authors and Affiliations

  1. Department of Material and Biological Chemistry, Faculty of Science, Yamagata University, Yamagata, 990-8560, Japan

    Shin-ichi Kondo & Fubuki Takahashi

  2. Department of Chemistry and Chemical Biology, Graduate School of Engineering, Gunma University, Kiryu, Gunma, 376-8515, Japan

    Naoya Watanabe, Nobuhiro Takeda & Masafumi Unno

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  1. Shin-ichi Kondo
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  2. Naoya Watanabe
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Correspondence to Shin-ichi Kondo.

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Kondo, Si., Watanabe, N., Takahashi, F. et al. Synthesis and photophysical properties of 2,2′-binaphthalene-based receptor bearing trimethylsilyl groups to improve the solubility. J Incl Phenom Macrocycl Chem 75, 31–38 (2013). https://doi.org/10.1007/s10847-012-0142-8

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