Abstract
The use of triazole CH•••anion hydrogen bonds, strong and easy to install, has expanded dramatically since 2008. Various aryl-triazole derivatives have been synthesized and investigated to obtain fundamental understandings of anion stabilization as well as to develop new receptors for applications. Receptors have now been created to make use of triazole, triazolium, or iodotriazolium. The triazole CH•••anion binding motif has also been utilized in sophisticated structures such as interlocked molecules and toward fluorescent sensors and ion-selective electrodes. Furthermore, demonstrations on the transport of anions across membranes and studies of light-induced anion regulation have broadened the scope of application for this new anion binding motif. This chapter will focus on these recent developments.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsAbbreviations
- Bn:
-
Benzyl
- CH2Cl2 :
-
Dichloromethane
- CHCl3 :
-
Chloroform
- CuAAC:
-
Copper(I)-catalyzed azide-alkyne cycloaddition
- ESP:
-
Electrostatic potential
- ISE:
-
Ion-selective electrode
- K a :
-
Association constant
- NMR:
-
Nuclear magnetic resonance
- POPC:
-
1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine
- TBA+ :
-
Tetrabutylammonium cation
References
Bianchi A, Bowman-James K, García-España E (1997) Supramolecular chemistry of anions. Wiley-VCH, New York
Sessler JL, Gale PA, Cho W-S (2006) Anion receptor chemistry. RSC Publishing, Cambridge, UK
Desiraju GR, Steiner T (1999) The weak hydrogen bond. Oxford University Press Inc, New York
Rostovtsev VV, Green LG, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed 41:2596
Tornøe CW, Christensen C, Meldal M (2002) J Org Chem 67:3057
Kwon JY, Jang YJ, Kim SK, Lee K-H, Kim JS, Yoon J (2004) J Org Chem 69:5155
Ilioudis CA, Tocher DA, Steed JW (2004) J Am Chem Soc 126:12395
Chmielewski MJ, Charon M, Jurczak J (2004) Org Lett 6:3501
Farnham WB, Roe DC, Dixon DA, Calabrese JC, Harlow RL (1990) J Am Chem Soc 112:7707
Sutor DJ (1963) J Chem Soc 1105
Bryantsev VS, Hay BP (2005) J Am Chem Soc 127:8282
Berryman OB, Sather AC, Hay BP, Meisner JS, Johnson DW (2008) J Am Chem Soc 130:10895
Zhu SS, Staats H, Brandhorst K, Grunenberg J, Gruppi F, Dalcanale E, Lützen A, Rissanen K, Schalley CA (2008) Angew Chem Int Ed 47:788
Yoon D-W, Gross DE, Lynch VM, Sessler JL, Hay BP, Lee C-H (2008) Angew Chem Int Ed 47:5038
Palmer MH, Findlay RH, Gaskell AJ (1974) J Chem Soc Perkin Trans 2:420
Li Y, Flood AH (2008) Angew Chem Int Ed 47:2649
Li Y, Flood AH (2008) J Am Chem Soc 130:12111
Hirose K (2001) J Inclusion Phenom Macrocyclic Chem 39:193
Li Y, Pink M, Karty JA, Flood AH (2008) J Am Chem Soc 130:17293
Hua Y, Ramabhadran RO, Uduehi EO, Karty JA, Raghavachari K, Flood AH (2011) Chem Eur J 17:312
Bandyopadhyay I, Raghavachari K, Flood AH (2009) ChemPhysChem 10:2535
Juwarker H, Lenhardt JM, Pham DM, Craig SL (2008) Angew Chem Int Ed 47:3740
Meudtner RM, Hecht S (2008) Angew Chem Int Ed 47:4926
Kolb HC, Finn MG, Sharpless KB (2001) Angew Chem Int Ed 40:2004
Hua Y, Flood AH (2010) Chem Soc Rev 39:1262
McDonald KP, Hua Y, Flood AH (2010) Top Heterocycl Chem 24:341
Cabbines DK, Margerum DW (1969) J Am Chem Soc 91:6540
Sessler JL, Cai J, Gong H-Y, Yang X, Arambula JF, Hay BP (2010) J Am Chem Soc 132:14058
Zhao Y, Li Y, Li Y, Huang C, Liu H, Lai S-W, Che C-M, Zhu D (2010) Org Biomol Chem 8:3923
Alunni S, Pero A, Reichenbach G (1998) J Chem Soc Perkin Trans 2:1747
Ramabhadran RO, Hua Y, Li Y, Flood AH, Raghavachari K (2011) Chem Eur J 17:9123
Meot-Ner M, Cybulski SM, Scheiner S, Liebman JF (1988) J Phys Chem 92:2138
Alabugin IV, Zeidan TA (2002) J Am Chem Soc 124:3175
Juwarker H, Lenhardt JM, Castillo JC, Zhao E, Krishnamurthy S, Jamiolkowski RM, Kim K-H, Craig SL (2009) J Org Chem 74:8924
Hua Y, Ramabhadran RO, Karty JA, Raghavachari K, Flood AH (2011) Chem Commun 47:5979
Lee S, Hua Y, Park H, Flood AH (2010) Org Lett 12:2100
Haridas V, Sahu S, Venugopalan P (2011) Tetrahedron 67:727
Wang Y, Xiang J, Jiang H (2011) Chem Eur J 17:613
García F, Torres MR, Matesanz E, Sánchez L (2011) Chem Commun 47:5016
Schulze B, Friebe C, Hager HD, Günther W, Köhn U, Jahn BO, Görls H, Schubert US (2010) Org Lett 12:2710
Zheng H, Zhou W, Lv J, Yin X, Li Y, Liu H, Li Y (2009) Chem Eur J 15:13253
Mullen KM, Mercurio J, Serpell CJ, Beer PD (2009) Angew Chem Int Ed 48:4781
Kilah NL, Wise MD, Serpell CJ, Thompson AL, White NG, Christensen KE, Beer PD (2010) J Am Chem Soc 132:11893
Kim JS, Park SY, Kim SH, Thuéry P, Souane R, Matthews SE, Vicens J (2010) Bull Korean Chem Soc 31:624
Zahran EM, Hua Y, Li Y, Flood AH, Bachas LG (2010) Anal Chem 82:368
Zahran EM, Hua Y, Lee S, Flood AH, Bachas LG (2011) Anal Chem 83:3455
Doyle AG, Jacobsen EN (2007) Chem Rev 107:5713
Ohmatsu K, Kiyokawa M, Ooi T (2011) J Am Chem Soc 133:1307
Davis AP, Sheppard DN, Smith BD (2007) Chem Soc Rev 36:348
Yano M, Tong CC, Light ME, Schmidtchen FP, Gale PA (2010) Org Biomol Chem 8:4356
Shinkai S, Nakaji T, Ogawa T, Shigematsu K, Manabe O (1981) J Am Chem Soc 103:111
Wang Y, Bie F, Jiang H (2010) Org Lett 12:3630
Khan A, Kaiser C, Hecht S (2006) Angew Chem Int Ed 45:1878
Hua Y, Flood AH (2010) J Am Chem Soc 132:12838
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2012 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Lee, S., Flood, A.H. (2012). Binding Anions in Rigid and Reconfigurable Triazole Receptors. In: Košmrlj, J. (eds) Click Triazoles. Topics in Heterocyclic Chemistry, vol 28. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2011_70
Download citation
DOI: https://doi.org/10.1007/7081_2011_70
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-29428-0
Online ISBN: 978-3-642-29429-7
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)