Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2010(17): 2553-2556
DOI: 10.1055/s-0030-1258578
DOI: 10.1055/s-0030-1258578
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Colorimetric Fluoride Sensor Based on a Bisthiourea Functionalized Molecular Clip
Further Information
Received
10 June 2010
Publication Date:
23 September 2010 (online)
Publication History
Publication Date:
23 September 2010 (online)
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
- Supporting Information for this article is available online:
- Supporting Information
- 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 -
1c
Beer PD.Gale PA. Angew. Chem. Int. Ed. 2001, 40: 486 -
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 -
1f
Caltagitone C.Gale PA. Chem. Soc. Rev. 2009, 38: 520 -
1g
Gale PA.Garcia-Garrido SE.Garric J. Chem. Soc. Rev. 2008, 37: 151 -
2a
Krik KL. Biochemistry of Halogens and Inorganic Halides Plenum Press; New York: 1991. 591: -
2b
Kleerekoper M. Endocrinol. Metab. Clin. North Am. 1998, 27: 441 - 3
Cametti M.Rissanen K. Chem. Commun. 2009, 2809 -
4a
Miyaji H.Sato W.Sessler JL. Angew. Chem. Int. Ed. 2000, 39: 1777 -
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 -
4d
Anzenbacher P.Try AC.Miyaji H.Jursíková K.Lynch VM.Marquez M.Sessler JL. J. Am. Chem. Soc. 2000, 122: 10268 -
4e
Woods CJ.Camiolo S.Light ME.Coles SJ.Hursthouse MB.King MA.Gale PA.Essex JW. J. Am. Chem. Soc. 2002, 124: 8644 -
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 -
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 -
5d
Lee JY.Cho EJ.Mukamel S.Nam KC. J. Org. Chem. 2004, 69: 943 -
5e
Jiménez D.Martínez-Máñez R.Sancenón F.Soto J. Tetrahedron Lett. 2002, 43: 2823 -
5f
Thangadurai TD.Singh NJ.Hwang I.-C.Lee JW.Chandran RP.Kim KS. J. Org. Chem. 2007, 72: 5461 -
5g
Kwon Y.Jang YJ.Kim SK.Lee K.-H.Kim JS.Yoon J. J. Org. Chem. 2004, 69: 5155 -
5h
Jose DA.Kumar DK.Ganguly B.Das A. Org. Lett. 2004, 6: 3445 -
5i
Cho EJ.Ryu BJ.Lee YJ.Nam KC. Org. Lett. 2005, 7: 2607 -
5j
Boiocchi M.Boca LD.Gómez DE.Fabbrizzi L.Licchelli M.Monzan E. J. Am. Chem. Soc. 2004, 126: 16507 -
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 -
6i
Liu XY.Bai DR.Wang S. Angew. Chem. Int. Ed. 2006, 45: 5475 -
6j
Hudnall TW.Gabbaï FP. J. Am. Chem. Soc. 2007, 129: 11978 -
6k
Melaimi M.Gabbaï FP. J. Am. Chem. Soc. 2005, 127: 9680 -
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 -
7c
Kang SO.Day VW.Bowman-James K. J. Org. Chem. 2010, 75: 277 -
8a
Miyaji H.Sessler JL. Angew. Chem. Int. Ed. 2001, 40: 154 -
8b
Bhosale SV.Bhosale SV.Kalyankar MB.Langford SJ. Org. Lett. 2009, 11: 5418 -
8c
Mizuno T.Wei W.-H.Eller LR.Sessler JL. J. Am. Chem. Soc. 2002, 124: 1134 -
8d
Sun Y.Wang S. Inorg. Chem. 2009, 48: 3755 -
8e
Dydio P.Zieliński T.Jurczak J. J. Org. Chem. 2009, 74: 1525 -
8f
Lin Y.-C.Chen C.-T. Org. Lett. 2009, 11: 4858 -
8g
Chawla HM.Shrivastava R.Sahu SN. New J. Chem. 2008, 32: 1999 -
8h
Kim HJ.Kim SK.Lee JY.Kim JS. J. Org. Chem. 2006, 71: 6611 -
8i
Zhao P.Jiang J.Leng B.Tian H. Macromol. Rapid Commun. 2009, 30: 1715 -
8j
Peng X.Wu Y.Fan J.Tian M.Han K. J. Org. Chem. 2005, 70: 10524 -
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 - 9
Rowan AE.Elemans JAAW.Nolte RJM. Acc. Chem. Res. 1999, 32: 995 - 10
Rebek J. Angew. Chem. Int. Ed. 2005, 44: 2068 -
11a
Lagona J.Mukhopadhyay P.Chakrabarti S.Isaacs L. Angew. Chem. Int. Ed. 2005, 44: 4844 -
11b
Lee JW.Samal S.Selvapalam N.Kim H.-J.Kim K. Acc. Chem. Res. 2003, 36: 621 -
12a
Chiang PT.Cheng PN.Lin CF.Liu YH.Lai CC.Peng SM.Chiu SH. Chem. Eur. J. 2006, 12: 865 -
12b
Chiang PT.Chen NC.Lai CC.Chiu SH. Chem. Eur. J. 2008, 14: 6546 -
12c
Kang J.Jo J.In S. Tetrahedron Lett. 2004, 45: 5225 -
12d
In S.Kang J. Tetrahedron Lett. 2005, 46: 7165 - 13
Hu SL.She NF.Yin GD.Guo HZ.Wu AX.Yang CL. Tetrahedron Lett. 2007, 48: 1591 - 14
She NF.Gao M.Cao LP.Wu AX.Isaacs L. Org. Lett. 2009, 11: 2603 - 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 -
15c
Galf PA. Acc. Chem. Res. 2006, 39: 465 -
15d
Li X.Wu Y.-D.Yang D. Acc. Chem. Res. 2008, 41: 1428 - 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 - 18
Job P. Ann. Chim. 1928, 9: 113
References and Notes
See Supporting Information.