Abstract
A novel dicalix[4]pyrrolyl-substituted 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dye I with an absorption peak at approximately 670 nm and an emission peak at about 690 nm was prepared. As an anion receptor, I displayed a red shift in absorption spectra and fluorescence quenching in varying degrees in the presence of F−, AcO−, H2PO4−, or Cl−. Compared with the parent calix[4]pyrrole, a representative anion receptor, I exhibited a stronger affinity to these anions due to the formation of a sandwich complex through multiple hydrogen-bonding interactions.
[1] Anzenbacher, P., Jr., Jursíková, K., & Sessler, J. L. (2000). Second generation calixpyrrole anion sensors. Journal of the American Chemical Society, 122, 9350–9351. DOI: 10.1021/ja001308t. http://dx.doi.org/10.1021/ja001308t10.1021/ja001308tSearch in Google Scholar
[2] Ballou, B., Ernst, L. A., & Waggoner, A. S. (2005). Fluorescence imaging of tumors in vivo. Current Medicinal Chemistry, 12, 795–805. DOI: 10.2174/0929867053507324. http://dx.doi.org/10.2174/092986705350732410.2174/0929867053507324Search in Google Scholar
[3] Bianchi, A., Bowman-James, K., & Garcia-Espana, E. (1997). Supramolecular chemistry of anions. New York, NY, USA: Wiley-VCH. Search in Google Scholar
[4] Caltagirone, C., & Gale, P. A. (2009). Anion receptor chemistry: highlights from 2007. Chemical Society Reviews, 38, 520–563. DOI: 10.1039/b806422a. http://dx.doi.org/10.1039/b806422a10.1039/B806422ASearch in Google Scholar
[5] Connors, K. A. (1987). Binding constants: The measurement of molecular complex stability. New York, NY, USA: Wiley-VCH. Search in Google Scholar
[6] Coskun, A., Baytekin, B. T., & Akkaya, E. U. (2003). Novel fluorescent chemosensor for anions via modulation of oxidative PET: a remarkable 25-fold enhancement of emission. Tetrahedron Letters, 44, 5649–5651. DOI: 10.1016/S0040-4039(03)01365-0. http://dx.doi.org/10.1016/S0040-4039(03)01365-010.1016/S0040-4039(03)01365-0Search in Google Scholar
[7] Ekmekci, Z., Yilmaz, M. D., & Akkaya, E. U. (2008). A monostyryl-boradiazaindacene (BODIPY) derivative as colorimetric and fluorescent probe for cyanide ions. Organic Letters, 10, 461–464. DOI: 10.1021/ol702823u. http://dx.doi.org/10.1021/ol702823u10.1021/ol702823uSearch in Google Scholar PubMed
[8] Gale, P. A. (2008). Synthetic indole, carbazole, biindole and indolocarbazole-based receptors: applications in anion complexation and sensing. Chemical Communications, 38, 4525–4540. DOI: 10.1039/b809508f. http://dx.doi.org/10.1039/b809508f10.1039/b809508fSearch in Google Scholar PubMed
[9] Gale, P. A., Sessler, J. L., Král, V., & Lynch, V. (1996). Calix[4]pyrroles: Old yet new anion-binding agents. Journal of the American Chemical Society, 118, 5140–5141. DOI: 10.1021/ja960307r. http://dx.doi.org/10.1021/ja960307r10.1021/ja960307rSearch in Google Scholar
[10] Gunnlaugsson, T., Glynn, M., Tocci (née Hussey), G. M., Kruger, P. E., & Pfeffer, F. M. (2006). Anion recognition and sensing in organic and aqueous media using luminescent and colorimetric sensors. Coordination Chemistry Reviews, 250, 3094–3117. DOI: 10.1016/j.ccr.2006.08.017. http://dx.doi.org/10.1016/j.ccr.2006.08.01710.1016/j.ccr.2006.08.017Search in Google Scholar
[11] Kollmannsberger, M., Rurack, K., Resch-Genger, U., & Daub, J. (1998). Ultrafast charge transfer in amino-substituted boron dipyrromethene dyes and its inhibition by cation complexation: A new design concept for highly sensitive fluorescent probes. The Journal of Physical Chemistry A, 102, 10211–10220. DOI: 10.1021/jp982701c. http://dx.doi.org/10.1021/jp982701c10.1021/jp982701cSearch in Google Scholar
[12] Loudet, A., & Burgess, K. (2007). BODIPY dyes and their derivatives: Syntheses and spectroscopic properties. Chemical Reviews, 107, 4891–4932. DOI: 10.1021/cr078381n. http://dx.doi.org/10.1021/cr078381n10.1021/cr078381nSearch in Google Scholar PubMed
[13] Martínez-Máñez, R., & Sancenón, F. (2003). Fluorogenic and chromogenic chemosensors and reagents for aions. Chemical Reviews, 103, 4419–4476. DOI: 10.1021/cr010421e. http://dx.doi.org/10.1021/cr010421e10.1021/cr010421eSearch in Google Scholar
[14] Mikláš, R., Kasák, P., Devínsky, F., & Putala, M. (2009). Fluoride anion sensing using colorimetric reagents containing binaphthyl moiety and urea binding site. Chemical Papers, 63, 709–715. DOI: 10.2478/s11696-009-0079-6. http://dx.doi.org/10.2478/s11696-009-0079-610.2478/s11696-009-0079-6Search in Google Scholar
[15] Miyaji, H., Anzenbacher, P., Jr., Sessler, J. L., Bleasdale, E. R., & Gale, P. A. (1999). Anthracene-linked calix[4]pyrroles: Fluorescent chemosensors for anions. Chemical Communications, 17, 1723–1724. DOI: 10.1039/a905054j. http://dx.doi.org/10.1039/a905054j10.1039/a905054jSearch in Google Scholar
[16] Miyaji, H., Sato, W., & Sessler, J. L. (2000). Naked-eye detection of anions in dichloromenthane: Colorimetric anion sensors based on calix[4]pyrrole. Angewandte Chemie International Edition, 39, 1777–17780. DOI: 10.1002/(SICI)1521-3773(20000515)39:10〈1777::AID-ANIE1777〉3.0.CO;2-E. http://dx.doi.org/10.1002/(SICI)1521-3773(20000515)39:10<1777::AID-ANIE1777>3.0.CO;2-E10.1002/(SICI)1521-3773(20000515)39:10<1777::AID-ANIE1777>3.0.CO;2-ESearch in Google Scholar
[17] Nishiyabu, R., & Anzenbacher, P., Jr. (2006). 1,3-indane-based chromogenic calixpyrroles with push-pull chromophores: Synthesis and anion sensing. Organic Letters, 8, 359–362. DOI: 10.1021/ol0521782. http://dx.doi.org/10.1021/ol052178210.1021/ol0521782Search in Google Scholar
[18] Piatek, P., Lynch, V. M., & Sessler, J. L. (2004). Calix[4]pyrrole[2]carbazole: A new kind of expanded calixpyrrole. Journal of the American Chemical Society, 126, 16073–16076. DOI: 10.1021/ja045218q. http://dx.doi.org/10.1021/ja045218q10.1021/ja045218qSearch in Google Scholar
[19] Qian, G., Li, X., & Wang, Z. (2009). Visible and near-infrared chemosensor for colorimetric and ratiometric detection of cyanide. Journal of Materials Chemistry, 19, 522–530. DOI: 10.1039/b813478b. http://dx.doi.org/10.1039/b813478b10.1039/B813478BSearch in Google Scholar
[20] Shiraishi, Y., Maehara, H., Sugii, T., Wang, D., & Hirai, T. (2009). A BODIPY-indole conjugate as a colorimetric and fluorometric probe for selective fluoride anion detection. Tetrahedron Letters, 50, 4293–4296. DOI: 10.1016/j.tetlet.2009.05.018. http://dx.doi.org/10.1016/j.tetlet.2009.05.01810.1016/j.tetlet.2009.05.018Search in Google Scholar
[21] Shortreed, M., Kopelman, R., Kuhn, M., & Hoyland, B. (1996). Fluorescent fiber-optic calcium sensor for physiological measurements. Analytical Chemistry, 68, 1414–1418. DOI: 10.1021/ac950944k. http://dx.doi.org/10.1021/ac950944k10.1021/ac950944kSearch in Google Scholar
[22] Valeur, B. (2002). Molecular fluorescence: Principles and applications. New York, NY, USA: Wiley-VCH. Search in Google Scholar
[23] Zhang, X., Li, C., Cheng, X., Wang, X., & Zhang, B. (2008a). A near-infrared croconium dye-based colorimetric chemodosimeter for biological thiols and cyanide anion. Sensors and Actuators B: Chemical, 129, 152–157. DOI: 10.1016/j.snb.2007.07.094. http://dx.doi.org/10.1016/j.snb.2007.07.09410.1016/j.snb.2007.07.094Search in Google Scholar
[24] Zhang, X., Xiao, Y., & Qian, X. (2008b). Highly efficient energy transfer in the light harvesting system composed of three kinds of boron-dipyrromethene derivatives. Organic Letters, 10, 29–32. DOI: 10.1021/ol702381j. http://dx.doi.org/10.1021/ol702381j10.1021/ol702381jSearch in Google Scholar PubMed
© 2011 Institute of Chemistry, Slovak Academy of Sciences
Articles in the same Issue
- Lipid retention of novel pressurized extraction vessels as a function of the number of static and flushing cycles, flush volume, and flow rate
- Determination of curcuminoids in substances and dosage forms by cyclodextrin-mediated capillary electrophoresis with diode array detection
- Interaction of Moringa oleifera seed lectin with humic acid
- Hybrid process scheme for the synthesis of ethyl lactate: conceptual design and analysis
- Zinc catalyst recycling in the preparation of (all-rac)-α-tocopherol from trimethylhydroquinone and isophytol
- Denitrification of simulated nitrate-rich wastewater using sulfamic acid and zinc scrap
- Anaerobic treatment of biodiesel by-products in a pilot scale reactor
- Preparation of magnesium hydroxide from nitrate aqueous solution
- Impact of the type of anodic film formed and deposition time on the characteristics of porous anodic aluminium oxide films containing Ni metal
- Synthesis and crystal and molecular structures of N,N′-methylenedipyridinium tetrachlorozincate(II) and N,N′-methylenedipyridinium tetrachlorocadmate(II)
- Effects of denaturing acid on the self-association behaviour of poly(ethylene glycol)-block-poly(γ-benzyl l-glutamate)-graft-poly(ethylene glycol) copolymer in ethanol
- Properties of poly(γ-benzyl l-glutamate) membrane modified by polyurethane containing carboxyl group
- Theoretical thermo-optical patterns relevant to glass crystallisation
- Morphology dependence of 1,2-diphenylethylenediamine-derived organogelator templates in solvents and their influence in the production of nanostructured silica
- Ferric hydrogensulphate as a recyclable catalyst for the synthesis of fluorescein derivatives
- An alternative synthetic process of p-acetaminobenzenesulfonyl chloride through combined chlorosulfonation by HClSO3 and PCl5
- An efficient and novel one-pot synthesis of 2,4,5-triaryl-1H-imidazoles catalyzed by UO2(NO3)2·6H2O under heterogeneous conditions
- Stereoselective synthesis of the polar part of mycestericins E and G
- A regio- and stereoselective three-component synthesis of 5-(trifluoromethyl)-4,5,6,7-tetrahydro-[1,2,4]triazolo[1,5-a]pyrimidine derivatives under solvent-free conditions
- Precautions in using global kinetic and thermodynamic models for characterization of drug release from multivalent supports
- A sandwich anion receptor by a BODIPY dye bearing two calix[4]pyrrole units
- What causes iron-sulphur bonds in active sites of one-iron superoxide reductase and two-iron superoxide reductase to differ?
- MTD-PLS and docking study for a series of substituted 2-phenylindole derivatives with oestrogenic activity
Articles in the same Issue
- Lipid retention of novel pressurized extraction vessels as a function of the number of static and flushing cycles, flush volume, and flow rate
- Determination of curcuminoids in substances and dosage forms by cyclodextrin-mediated capillary electrophoresis with diode array detection
- Interaction of Moringa oleifera seed lectin with humic acid
- Hybrid process scheme for the synthesis of ethyl lactate: conceptual design and analysis
- Zinc catalyst recycling in the preparation of (all-rac)-α-tocopherol from trimethylhydroquinone and isophytol
- Denitrification of simulated nitrate-rich wastewater using sulfamic acid and zinc scrap
- Anaerobic treatment of biodiesel by-products in a pilot scale reactor
- Preparation of magnesium hydroxide from nitrate aqueous solution
- Impact of the type of anodic film formed and deposition time on the characteristics of porous anodic aluminium oxide films containing Ni metal
- Synthesis and crystal and molecular structures of N,N′-methylenedipyridinium tetrachlorozincate(II) and N,N′-methylenedipyridinium tetrachlorocadmate(II)
- Effects of denaturing acid on the self-association behaviour of poly(ethylene glycol)-block-poly(γ-benzyl l-glutamate)-graft-poly(ethylene glycol) copolymer in ethanol
- Properties of poly(γ-benzyl l-glutamate) membrane modified by polyurethane containing carboxyl group
- Theoretical thermo-optical patterns relevant to glass crystallisation
- Morphology dependence of 1,2-diphenylethylenediamine-derived organogelator templates in solvents and their influence in the production of nanostructured silica
- Ferric hydrogensulphate as a recyclable catalyst for the synthesis of fluorescein derivatives
- An alternative synthetic process of p-acetaminobenzenesulfonyl chloride through combined chlorosulfonation by HClSO3 and PCl5
- An efficient and novel one-pot synthesis of 2,4,5-triaryl-1H-imidazoles catalyzed by UO2(NO3)2·6H2O under heterogeneous conditions
- Stereoselective synthesis of the polar part of mycestericins E and G
- A regio- and stereoselective three-component synthesis of 5-(trifluoromethyl)-4,5,6,7-tetrahydro-[1,2,4]triazolo[1,5-a]pyrimidine derivatives under solvent-free conditions
- Precautions in using global kinetic and thermodynamic models for characterization of drug release from multivalent supports
- A sandwich anion receptor by a BODIPY dye bearing two calix[4]pyrrole units
- What causes iron-sulphur bonds in active sites of one-iron superoxide reductase and two-iron superoxide reductase to differ?
- MTD-PLS and docking study for a series of substituted 2-phenylindole derivatives with oestrogenic activity