Selective fluoride ion recognition by a thiourea based receptor linked acridinedione functionalized gold nanoparticles

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 217, Issue 2-3, 2011, Pages 313-320

  Velu, R ^a   Ramakrishnan, V T ^a   Ramamurthy, P ^a  

^a UNIVERSITY OF MADRAS   (India)

Author keywords

Acridinedione; Fluorescence; Gold nanoparticles; Photoinduced electron transfer; Sensors

Indexed keywords

EID: 79451470761     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2010.10.025     Document Type: Article

References (45)

1. F.P. Schmidtchen, and M. Berger Artificial organic host molecules for anions Chem. Rev. 97 1997 1609 1643
2. P.D. Beer, and P.A. Gale Anion recognition and sensing: the state of the art and future perspectives Angew. Chem. Int. Ed. 40 2001 486 516
3. P.A. Gale, Special issue: 35 years of synthetic anion receptor chemistry Coord. Chem. Rev. 240 2003 1
4. C.R. Bondy, and S.J. Loeb Amide based receptors for anions Coord. Chem. Rev. 240 2003 77 99
5. K.L. Kirk Biochemistry of the Halogens and Inorganic Halides 1991 Plenum Press New York 58
6. J.M. Tomich, D. Wallace, K. Henderson, K.E. Mitchell, G. Radke, R. Brandt, C.A. Ambler, A.J. Scott, J. Grantham, L. Sullivan, and T. Iwamoto Aqueous solubilization of transmembrance peptide sequences with retention of membrane Biophys. J. 74 1998 256 267
7. S.K. Kim, J.H. Bok, R.A. Bartsch, J.Y. Lee, and J.S. Kim A fluoride-selective PCT chemosensor based on formation of a static pyrene excimer Org. Lett. 7 2005 4839 4842
8. P.A. Gale Amidopyrroles: from anion receptors to membrane transport agents Chem. Commun. 2005 3761 3772
9. S. Camiolo, P.A. Gale, M.B. Hursthouse, M.E. Light, and C.N. Warriner 2,5-Dimidofuran anion receptors Tetrahedron Lett. 44 2003 1367 1369
10. D.H. Lee, K.H. Lee, and J.I. Hong An azophenol-based chromogenic anion sensor Org. Lett. 3 2001 5 8
11. D.H. Lee, H.Y. Lee, K.H. Lee, and J.I. Hong Selective anion sensing based on a dual-chromophore approach Chem. Commun. 2001 1188 1189
12. X. Zhang, L. Guo, F.Y. Wu, and Y.B. Jiang Development of fluorescent sensing of anions under excited-state intermolecular proton transfer signaling mechanism Org. Lett. 5 2003 2667 2670
13. K. Chellappan, N.J. Singh, I.C. Hwang, J.W. Lee, K.S. Kim, and A. Calix [4] Imidazolium [2] pyridine as an anion receptor Angew. Chem. Int. Ed. 44 2005 2899 2903
14. J.L. Sessler, S. Camiolo, and P.A. Gale Pyrrolic and polypyrrolic anion binding agents Coord. Chem. Rev. 240 2003 17 55
15. Z.C. Wen, and Y.B. Jiang Ratiometric dual fluorescencent receptors for anions under intramolecular charge transfer mechanism Tetrahedron 60 2004 11109 11115
16. F.Y. Wu, Z. Li, L. Guo, X. Wang, M.H. Lin, Y.F. Zhao, and Y.B. Jiang A unique NH- benzamidothiourea based anion sensors substituents effect on anion sensing of the ICT dual fluorescent N-(p-dimethylaminobenzamido)-N′- arylthioureas Org. Biomol. Chem. 4 2006 624 630
17. V. Thiagarajan, D. Thirumalai, V.T. Ramakrishnan, and P. Ramamurthy A novel colorimetric and fluorescent chemosensor for anions involving PET and ICT pathways Org. Lett. 7 2005 657 660
18. T. Gunnlaugsson, H.D.P. Ali, M. Glynn, P.E. Kruger, G.M. Hussey, F.M. Pfeffer, C.M.G. dos Santos, and J. Tierney Fluorescencent photoinduced electron transfer (PET) sensors for anions; from design to potential application J. Fluoresc. 15 2005 287 299
19. S.S. Sun, J.A. Anspach, A.J. Lees, and P.Y. Zavalij Synthesis and electrochemical, photophysical and anion binding properties of self-assembly heterometallic cyclophanes Organometallics 21 2002 673 685
20. J.S. Wu, J.H. Zhou, P.F. Wang, X.H. Zhang, and S.K. Wu New fluorescent chemosensor based on exciplex signaling mechanism Org. Lett. 7 2005 2133 2136
21. X. Peng, Y. Wu, J. Fan, M. Tian, and K. Han Colorimetric and ratiometric fluorescence sensing of fluoride: tuning selectivity in proton transfer J. Org. Chem. 70 2005 10524 10531
22. 2 fixation Tetrahedron Lett. 44 2003 8909 8913
23. S. Camiolo, P.A. Gale, M.B. Hursthouse, M.E. Light, and A.J. Shi Solution and solid-state studies of 3,4-dichloro-2,5-diamidopyrroles: formation of an unusual anionic narcissistic dimmer Chem. Commun. 2002 758 759
24. S. Camiolo, P.A. Gale, M.B. Hursthouse, and M.E. Light Nitrophenyl derivatives of pyrrole 2,5-diamides: structural behaviour, anion binding and colour change signalled deprotonation Org. Biomol. Chem. 1 2003 741 744
25. P.A. Gale, K. Navakhun, S. Camiolo, M.E. Light, and M.B. Hursthouse Anion-anion assembly: a new class of anionic supramolecular polymer containing 3,4-dichloro-2,5-diamido-substituted pyrrole anion dimers J. Am. Chem. Soc. 124 2002 11228 11229
26. P.A. Gale Anion receptor chemistry: highlights from 1999 Coord. Chem. Rev. 213 2001 79 128
27. D.E. Gomez, L. Fabbrizzi, and M. Licchelli Why, on interaction of urea-based receptors with fluoride, beautiful colors develop J. Org. Chem. 70 2005 5717 5720
28. M. Boiocchi, L. Del Boca, D.E. Gómez, L. Fabbrizzi, M. Licchelli, and E. Monzani Chem. Eur. J. 11 2005 3097 3104
29. M. Boiocchi, L. Del Boca, D.E. Gómez, L. Fabbrizzi, M. Licchelli, and E. Monzani Nature of urea-fluoride interaction: incipient and definitive proton transfer J. Am. Chem. Soc. 126 2004 16507 16514
30. M.T. Blazquez, F.M. Muniz, S. Saez, L.M. Simon, A. Alonso, C. Raposo, A. Lithgow, V. Alcazar, and J.R. Moran Acridone heterocycles as fluorescent sensors for anions Heterocycles 69 1 2006 73 81
31. S.E. García-Garrido, C. Caltagirone, M.E. Light, and P.A. Gale Acridinone-based anion receptors and sensors Chem. Commun. 2007 1450 1452
32. P. Shanmugasundaram, P. Murugan, V.T. Ramakrishnan, N. Srividya, and P. Ramamurthy Synthesis of acridinedione derivatives of laser dyes Heteroatom Chem. 7 1996 17 22
33. N. Srividya, P. Ramamurthy, P. Shanmugasundaram, and V.T. Ramakrishnan Synthesis, characterization, and electrochemistry of some acridine-1,8-dione dyes J. Org. Chem. 61 1996 5083 5089
34. C. Selvaraju, and P. Ramamurthy Excited-state behavior and photoionization of 1,8-acridinrdione dyes in micelles-comparison with NADH oxidation Chem. Eur. J. 10 2004 2253 2262
35. V. Thiagarajan, and P. Ramamurthy Fluorescent sensing of anions with acridinedione based neutral PET chemosensor Spectrochim. Acta A 67 2007 772 777
36. R. Velu, V.T. Ramakrishnan, and P. Ramamurthy Colorimetric and fluorometric chemosensors for selective signaling towards Ca2+ and Mg2+ by Aza-crown ether acridinedione functionalized gold nanoparticles Tetrahedron Lett. 2010 xxxx-xxxx
37. M. Brust, M. Walker, D. Bethell, D.J. Schffrin, and R. Whyman Synthesis of thiol-derivatised goldnanoparticles in a twophase liquid-liquid system J. Chem. Soc. Chem. Commun. 1994 801 802
38. Z. Yan-Li, Y. Chen, M. Wang, and Y. Yu Liu Multi [2] rotaxanes with gold nanoparticles as centers Org. Lett. 8 2006 1267 1270
39. R. Velu, P. Ashokkumar, V.T. Ramakrishnan, and P. Ramamurthy Molecular folding induced nanogold aggregation Tetrahedron Lett. 51 2010 3102 3105
40. N. Srividya, P. Ramamurthy, and V.T. Ramakrishnan Photophysical studies of acridine(1,8)dione dyes: a new class of laser dyes Spectrochim. Acta A 54 1998 245 253
41. N. Srividya, P. Ramamurthy, and V.T. Ramakrishnan Photooxidation of acridine(1,8) dione dyes: flash photolysis investigation of the mechanistic details Phys. Chem. Chem. Phys. 2 2000 5120 5126
42. V. Thiagarajan, C. Selvaraju, and P. Ramamurthy Excited state behavior of acridinedione dyes in PMMA matrix: in homogeneous broadening and enhancement of triplet J. Photochem. Photobiol. A: Chem. 157 2003 23 31
43. M.J. Hostetler, J.E. Wingate, C.J. Zhong, J.E. Harris, R.W. Vachet, M.R. Clark, J. David Londono, S.J. Green, J.J. Stokes, G.D. Wignall, G.L. Glish, M.D. Porter, N.D. Evans, and R.W. Murray Alkanethiolate gold cluster molecules with core diameters from 1.5 to 5.2 nm: core and monolayer properties as a function of core size Langmuir 14 1998 17 30
44. J.Y. Lee, E.J. Cho, S. Mukamel, and K.C. Nam Efficient fluoride-selective fluorescent host: experiment and theory J. Org. Chem. 69 2004 943 950
45. D.A. Jose, D.K. Kumar, and B. Ganguly Efficient and simple colorimetric fluoride ion sensor based on receptors having urea and thiourea binding sites Org. Lett. 6 2004 3445 3448