Download PDF
Synlett 2010(17): 2553-2556  
DOI: 10.1055/s-0030-1258578
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Colorimetric Fluoride Sensor Based on a Bisthiourea Functionalized Molecular Clip

Liping Cao, Jiaoyang Ding, Jungang Wang, Yan Chen, Meng Gao, Weijian Xue, Anxin Wu*
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, Central China Normal University, Wuhan 430079, P. R. of China
e-Mail: chwuax@mail.ccnu.edu.cn;
Further Information

Publication History

Received 10 June 2010
Publication Date:
23 September 2010 (online)

   Permissions and Reprints All articles of this category
Preview

Abstract

A new class of bisthiourea-functionalized molecular clips were designed and synthesized for anion recognition. Clip 1 showed excellent affinity to the biologically relevant fluoride ion in a 1:1 ratio as shown by UV-vis, ¹H and ¹9F NMR studies. Moreover, the binding was accompanied with visually noticeable color changes, enabling the compound to act as a colorimetric fluoride sensor.

Key words

glycoluril - molecular clip - fluoride - sensor - thiourea

    References and Notes

  • For recent books and reviews for anion receptors, see:
  • 1a Bianchi A. Bowman-James K. Garcia España E. Supramolecular Chemistry of Anions   Wiley-VCH; New York: 1997. 
  • 1b Gale PA. Coord. Chem. Res.  2003,  240:  191 
    Search in Google Scholar
  • 1c Beer PD. Gale PA. Angew. Chem. Int. Ed.  2001,  40:  486 
    Search in Google Scholar
  • 1d Sessler JL. Gale PA. Cho W.-S. Anion Receptor Chemistry   RSC Publishing; Cambridge / UK: 2006. 
  • 1e Schmidtchen FP. Berger M. Chem. Rev.  1997,  97:  1609 
    Search in Google Scholar
  • 1f Caltagitone C. Gale PA. Chem. Soc. Rev.  2009,  38:  520 
    Search in Google Scholar
  • 1g Gale PA. Garcia-Garrido SE. Garric J. Chem. Soc. Rev.  2008,  37:  151 
    Search in Google Scholar
  • 2a Krik KL. Biochemistry of Halogens and Inorganic Halides   Plenum Press; New York: 1991.  591: 
    Search in Google Scholar
  • 2b Kleerekoper M. Endocrinol. Metab. Clin. North Am.  1998,  27:  441 
    Search in Google Scholar
  • 3 Cametti M. Rissanen K. Chem. Commun.  2009,  2809 
    Crossref
  • 4a Miyaji H. Sato W. Sessler JL. Angew. Chem. Int. Ed.  2000,  39:  1777 
    Search in Google Scholar
  • 4b Miyaji H. Anzenbacher P. Sessler JL. Bleasdale ER. Gale PA. Chem. Commun.  1999,  1723 
  • 4c Anzenbacher P. Jursíková K. Sessler JL.
    J. Am. Chem. Soc.  2000,  122:  9350 
    Search in Google Scholar
  • 4d Anzenbacher P. Try AC. Miyaji H. Jursíková K. Lynch VM. Marquez M. Sessler JL. J. Am. Chem. Soc.  2000,  122:  10268 
    Search in Google Scholar
  • 4e Woods CJ. Camiolo S. Light ME. Coles SJ. Hursthouse MB. King MA. Gale PA. Essex JW. J. Am. Chem. Soc.  2002,  124:  8644 
    Search in Google Scholar
  • 4f Camiolo S. Gale PA. Chem. Commun.  2000,  1129 
  • 4g Gale PA. Sessler JL. Král V. Chem. Commun.  1998,  1 
  • 4h Black CB. Andrioletti B. Try AC. Ruiperez C. Sessler JL. J. Am. Chem. Soc.  1999,  121:  10438 
    Search in Google Scholar
  • 4i Scherer M. Sessler JL. Gebauer A. Lynch V. Chem. Commun.  1998,  85 
  • 4j Gale PA. Twyman LJ. Handlin CI. Sessler JL. Chem. Commun.  1999,  1851 
  • For selected examples, see:
  • 5a Kim SK. Yoon J. Chem. Commun.  2002,  770 
  • 5b Xu G. Tarr MA. Chem. Commun.  2004,  1050 
  • 5c Cho EJ. Moon JW. Ko SW. Lee JY. Kim SK. Yoon J. Nam KC. J. Am. Chem. Soc.  2003,  125:  12376 
    Search in Google Scholar
  • 5d Lee JY. Cho EJ. Mukamel S. Nam KC. J. Org. Chem.  2004,  69:  943 
    Search in Google Scholar
  • 5e Jiménez D. Martínez-Máñez R. Sancenón F. Soto J. Tetrahedron Lett.  2002,  43:  2823 
    Search in Google Scholar
  • 5f Thangadurai TD. Singh NJ. Hwang I.-C. Lee JW. Chandran RP. Kim KS. J. Org. Chem.  2007,  72:  5461 
    Search in Google Scholar
  • 5g Kwon Y. Jang YJ. Kim SK. Lee K.-H. Kim JS. Yoon J. J. Org. Chem.  2004,  69:  5155 
    Search in Google Scholar
  • 5h Jose DA. Kumar DK. Ganguly B. Das A. Org. Lett.  2004,  6:  3445 
    Search in Google Scholar
  • 5i Cho EJ. Ryu BJ. Lee YJ. Nam KC. Org. Lett.  2005,  7:  2607 
    Search in Google Scholar
  • 5j Boiocchi M. Boca LD. Gómez DE. Fabbrizzi L. Licchelli M. Monzan E. J. Am. Chem. Soc.  2004,  126:  16507 
    Search in Google Scholar
  • 6a Solé S. Gabbaï FP. Chem. Commun.  2004,  1284 
  • 6b Nicolas M. Fabre B. Simonet J. Chem. Commun.  1999,  1881 
  • 6c Cooper CR. Spencer N. James TD. Chem. Commun.  1998,  1365 
  • 6d Yamamoto H. Ori A. Ueda K. Dusemund C. Shinkai S. Chem. Commun.  1996,  407 
  • 6e Dusemund C. Sandanayake KRAS. Shinkai S. J. Chem. Soc., Chem. Commun.  1995,  333 
  • 6f Hudnall TW. Gabbaï FP. Chem. Commun.  2008,  4596 
  • 6g Agou T. Sekine M. Kobayashi J. Kawashima T. Chem. Commun.  2009,  1894 
  • 6h Bozdemir OA. Sozmen FS. Buyukcakir O. Guliyev R. Cakmak Y. Akkaya EU. Org. Lett.  2010,  12:  1400 
    Search in Google Scholar
  • 6i Liu XY. Bai DR. Wang S. Angew. Chem. Int. Ed.  2006,  45:  5475 
    Search in Google Scholar
  • 6j Hudnall TW. Gabbaï FP. J. Am. Chem. Soc.  2007,  129:  11978 
    Search in Google Scholar
  • 6k Melaimi M. Gabbaï FP. J. Am. Chem. Soc.  2005,  127:  9680 
    Search in Google Scholar
  • 6l Xu Z. Kim SK. Han SJ. Lee C. Kociok-Kohn G. James TD. Yoon J. Eur. J. Org. Chem.  2009,  3058 
  • 7a Piatek P. Jurczak J. Chem. Commun.  2002,  2450 
  • 7b Korendovych IV. Cho M. Makhlynets OV. Butler PL. Staples RJ. Rybak-Akimova EV. J. Org. Chem.  2008,  73:  4771 
    Search in Google Scholar
  • 7c Kang SO. Day VW. Bowman-James K. J. Org. Chem.  2010,  75:  277 
    Search in Google Scholar
  • 8a Miyaji H. Sessler JL. Angew. Chem. Int. Ed.  2001,  40:  154 
    Search in Google Scholar
  • 8b Bhosale SV. Bhosale SV. Kalyankar MB. Langford SJ. Org. Lett.  2009,  11:  5418 
    Search in Google Scholar
  • 8c Mizuno T. Wei W.-H. Eller LR. Sessler JL. J. Am. Chem. Soc.  2002,  124:  1134 
    Search in Google Scholar
  • 8d Sun Y. Wang S. Inorg. Chem.  2009,  48:  3755 
    Search in Google Scholar
  • 8e Dydio P. Zieliński T. Jurczak J. J. Org. Chem.  2009,  74:  1525 
    Search in Google Scholar
  • 8f Lin Y.-C. Chen C.-T. Org. Lett.  2009,  11:  4858 
    Search in Google Scholar
  • 8g Chawla HM. Shrivastava R. Sahu SN. New J. Chem.  2008,  32:  1999 
    Search in Google Scholar
  • 8h Kim HJ. Kim SK. Lee JY. Kim JS. J. Org. Chem.  2006,  71:  6611 
    Search in Google Scholar
  • 8i Zhao P. Jiang J. Leng B. Tian H. Macromol. Rapid Commun.  2009,  30:  1715 
    Search in Google Scholar
  • 8j Peng X. Wu Y. Fan J. Tian M. Han K. J. Org. Chem.  2005,  70:  10524 
    Search in Google Scholar
  • 8k Bates GW. Gale PA. Light ME. Chem. Commun.  2007,  2121 
  • 8l Wang Q. Xie Y. Ding Y. Li X. Zhu W. Chem. Commun.  2010,  46:  3669 
    Search in Google Scholar
  • 9 Rowan AE. Elemans JAAW. Nolte RJM. Acc. Chem. Res.  1999,  32:  995 
    CrossrefSearch in Google Scholar
  • 10 Rebek J. Angew. Chem. Int. Ed.  2005,  44:  2068 
    CrossrefSearch in Google Scholar
  • 11a Lagona J. Mukhopadhyay P. Chakrabarti S. Isaacs L. Angew. Chem. Int. Ed.  2005,  44:  4844 
    Search in Google Scholar
  • 11b Lee JW. Samal S. Selvapalam N. Kim H.-J. Kim K. Acc. Chem. Res.  2003,  36:  621 
    Search in Google Scholar
  • 12a Chiang PT. Cheng PN. Lin CF. Liu YH. Lai CC. Peng SM. Chiu SH. Chem. Eur. J.  2006,  12:  865 
    Search in Google Scholar
  • 12b Chiang PT. Chen NC. Lai CC. Chiu SH. Chem. Eur. J.  2008,  14:  6546 
    Search in Google Scholar
  • 12c Kang J. Jo J. In S. Tetrahedron Lett.  2004,  45:  5225 
    Search in Google Scholar
  • 12d In S. Kang J. Tetrahedron Lett.  2005,  46:  7165 
    Search in Google Scholar
  • 13 Hu SL. She NF. Yin GD. Guo HZ. Wu AX. Yang CL. Tetrahedron Lett.  2007,  48:  1591 
    CrossrefSearch in Google Scholar
  • 14 She NF. Gao M. Cao LP. Wu AX. Isaacs L. Org. Lett.  2009,  11:  2603 
    CrossrefSearch in Google Scholar
  • For recent reviews, see:
  • 15a Galf PA. Amide- and Urea-Based Anion Receptors, In Encyclopedia of Supramolecular Chemistry   Marcel Dekker; New York: 2004.  p.31-41  
  • 15b Amendola V. Esteban-Gómez D. Fabbrizzi L. Licchelli M. Acc. Chem. Res.  2006,  39:  343 
    Search in Google Scholar
  • 15c Galf PA. Acc. Chem. Res.  2006,  39:  465 
    Search in Google Scholar
  • 15d Li X. Wu Y.-D. Yang D. Acc. Chem. Res.  2008,  41:  1428 
    Search in Google Scholar
  • 16 Due to the dimerization of molecular clips, we perform these experiments in MeCN-DMSO solvent system. The stabilities of hydrogen-bonded aggregates destroyed by DMSO, see: Mammen M. Simanek EE. Whitesides GM. J. Am. Chem. Soc.  1996,  118:  12614 
    CrossrefSearch in Google Scholar
  • 18 Job P. Ann. Chim.  1928,  9:  113 
    Search in Google Scholar
17

See Supporting Information.