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DOI: 10.1055/s-0029-1219197
Click Chemistry Approach to Fluorescence-Based Polybinaphthyls Incorporating a Triazole Moiety for Hg²+ Recognition
Publikationsverlauf
Publikationsdatum:
14. Januar 2010 (online)

Abstract
Optically active polybinaphthyls incorporating triazole moieties were obtained by polymerization of (R)-6,6′-dibutyl-3,3′-diethynyl-2,2′-bisoctoxy-1,1′-binaphthyl and 1,4-diazidobenzene through click reactions. This is the first example of click-generated polybinaphthyls. The responsive optical properties of the polymer upon addition of various metal ions were investigated by fluorescence and UV/Vis spectral studies. The results indicate that the triazole moiety is a receptor that shows excellent fluorescence response for Hg²+ recognition without interference from other metal ions.
Key words
alkyne-azide cycloaddition - triazole receptors - optically active polybinaphthyls - mercury ion recognition
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- 1a
Pu L. Chem. Rev. 2004, 104: 1687Reference Ris Wihthout Link - 1b
Pu L. Chem. Rev. 1998, 98: 2405Reference Ris Wihthout Link - 1c
Liu Y.Zhang S.Miao Q.Zheng L.Zong L.Cheng Y. Macromolecules 2007, 40: 4839Reference Ris Wihthout Link - 1d
Liu Y.Zong L.Zheng L.Wu L.Cheng Y. Polymer 2007, 48: 6799Reference Ris Wihthout Link - 1e
Deussen HJ.Hendrickx E.Boutton C.Krog D.Clays K.Bechgaard K.Persoons A.Bjørnholm T. J. Am. Chem. Soc. 1996, 118: 6841Reference Ris Wihthout Link - 1f
Koeckelberghs G.Verbiest T.Vangheluwe M.De Groof L.Asselberghs I.Picard I.Clays K.Persoons A.Samyn C. Chem. Mater. 2005, 17: 118Reference Ris Wihthout Link - 1g
Li ZB.Pu L. J. Mater. Chem. 2005, 15: 2860Reference Ris Wihthout Link - 2a
Zhang Z.Wu D.Guo X.Qian X.Lu Z.Zu Q.Yang Y.Duan L.He Y.Feng Z. Chem. Res. Toxicol. 2005, 18: 1814Reference Ris Wihthout Link - 2b
Nolan EM.Lippard SJ. Chem. Rev. 2008, 108: 3443Reference Ris Wihthout Link - 2c
Kim IB.Dunkhorst A.Gilbert J.Bunz UHF. Macromolecules 2005, 38: 4560Reference Ris Wihthout Link - 2d
Fan LJ.Jones WE. J. Am. Chem. Soc. 2006, 128: 6784Reference Ris Wihthout Link - 2e
Liu SJ.Fang C.Zhao Q.Fan QL.Huang W. Macromol. Rapid Commun. 2008, 29: 1212Reference Ris Wihthout Link - 3a
Rostovtsev VV.Green LG.Fokin VV.Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 2596Reference Ris Wihthout Link - 3b
Tornøe CW.Christensen C.Meldal M. J. Org. Chem. 2002, 67: 3057Reference Ris Wihthout Link - 4a
Malkoch M.Schleicher K.Drockenmuller E.Hawker CJ.Russell TP.Wu P.Fokin VV. Macromolecules 2005, 38: 3663Reference Ris Wihthout Link - 4b
Lee JW.Kim JH.Han SC.Shin WS.Jin SH. Macromolecules 2006, 39: 2418Reference Ris Wihthout Link - 5
Zeng Q.Li Z.Li Z.Ye C.Qin J.Tang BZ. Macromolecules 2007, 40: 5634 - 6a
Tsarevsky NV.Sumerlin BS.Matyjaszewski K. Macromolecules 2005, 38: 3558Reference Ris Wihthout Link - 6b
Gao HF.Matyjaszewski K. Macromolecules 2006, 39: 4960Reference Ris Wihthout Link - 7
Li Y.Benicewicz BC. Macromolecules 2008, 41: 7986 - 8a
Tamanini E.Katewa A.Sedger LM.Todd MH.Watkinson M. Inorg. Chem. 2009, 48: 319Reference Ris Wihthout Link - 8b
Varazo K.Xie F.Gulledge D.Wang Q. Tetrahedron Lett. 2008, 49: 5293Reference Ris Wihthout Link - 8c
Varazo K.Le Droumaguet C.Fullard K.UWang QU. Tetrahedron Lett. 2009, 50: 7032Reference Ris Wihthout Link - 8d
Zhu L.Lynch VM.Anslyn EV. Tetrahedron 2004, 60: 7267Reference Ris Wihthout Link - 9a
Bakbak S.Leech PJ.Carson BE.Saxena S.King WP.Bunz UHF. Macromolecules 2006, 39: 6793Reference Ris Wihthout Link - 9b
Van Steenis DJVC.David ORP.Van Strijdonck GPF.Van Maarseveen JH.Reek JNH. Chem. Commun. 2005, 4333Reference Ris Wihthout Link - 10
Minato M.Lahti PM. J. Am. Chem. Soc. 1997, 119: 2187 - 11
Huang X.Xu Y.Miao Q.Zong L.Hu H.Cheng Y. Polymer 2009, 50: 2793 - Procedure for the synthesis of chiral polymer, see:
- 12a
Morten M. Macromol. Rapid Commun. 2008, 29: 12Reference Ris Wihthout Link - 12b
A mixture of (R)-M1 (270.0 mg, 0.40 mmol), M2 (64.0 mg, 0.40 mmol), sodium ascorbate (10 mol%, 7.9 mg, 0.04 mmol) and CuSO4˙5H2O (5 mol%, 5.0 mg, 0.02 mmol) were dissolved in a mixture of THF (15 mL) and H2O (15 mL). The solution was stirred at r.t. for 2 d under an N2 atmosphere. The resulting polymer was filtered and washed with diluted ammonia water, H2O and methanol several times. Further purification could be achieved by dissolving the polymer in THF and precipitating in methanol again. The polymer was dried in vacuum to give the product as a yellow solid (282.6 mg, 85.0% yield). Polymer spectroscopic data: [α]D ²5 -483.9 (c 0.0083, THF); ¹H NMR (300 Hz, CDCl3): δ = 8.95 (br, 2 H), 8.72 (br, 2 H), 8.04 (br, 4 H), 7.82 (br, 2 H), 7.18 (br, 4 H), 3.68-3.64 (m, 2 H), 3.32-3.30 (m, 2 H), 2.80-2.76 (m, 4 H), 1.75-1.66 (m, 4 H), 1.46-1.39 (m, 4 H), 1.23-0.73 (m, 36 H). FT-IR (KBr): 3442, 3062, 2953, 2923, 2853, 1606, 1523, 1496, 1462, 1453, 1377, 1352, 1328, 1231, 1035, 1024 cm-¹. Anal. Calcd for (C54H67N6O2)n: C, 77.94; H, 8.12; N, 10.10. Found: C, 78.01; H, 8.04; N, 10.02.
Reference Ris Wihthout Link - 13
Karim MA.Cho YR.Park JS.Kim SC.Kim HJ.Lee JW.Gal YS.Jin SH. Chem. Commun. 2008, 1929 - 14a
Zou Y.Wan M.Sang G.Ye M.Li Y. Adv. Funct. Mater. 2008, 18: 2724Reference Ris Wihthout Link - 14b
Murphy CB.Zhang Y.Troxler T.Jones WE. J. Phys. Chem. B 2004, 108: 1537Reference Ris Wihthout Link - 15
Zhang Y.Murphy CB.Jones WE. Macromolecules 2002, 35: 630