Large fluorescence enhancement of a hemicyanine by supramolecular interaction with cucurbit[6]uril and its application as resettable logic gates

Dyes and Pigments

Volumn 93, Issue 1-3, 2012, Pages 1401-1407

  Li, Zhiyong ^a   Sun, Shiguo ^a   Liu, Fengyu ^a   Pang, Yi ^a,b   Fan, Jiangli ^a   Song, Fengling ^a   Peng, Xiaojun ^a  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

^b UNIVERSITY OF AKRON   (United States)

Author keywords

Cucurbit 6 uril; Fluorescence enhancement; Hemicyanine; Logic gate; Supramolecular chemistry; TICT

Indexed keywords

CUCURBIT[6]URIL; FLUORESCENCE ENHANCEMENT; HEMICYANINE; HEMICYANINE DYE; ION-DIPOLE INTERACTIONS; MOLECULAR LOGIC GATES; NMR MEASUREMENTS; OPTICAL SPECTRA; RECONFIGURABLE LOGIC; SUPRAMOLECULAR INTERACTIONS; TICT; TWISTED INTRA-MOLECULAR CHARGE TRANSFERS;

CHARGE TRANSFER; LOGIC GATES; STOICHIOMETRY; SUPRAMOLECULAR CHEMISTRY;

FLUORESCENCE;

EID: 80155161337     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2011.10.005     Document Type: Article

References (53)

1. J. Lagona, P. Mukhopadhyay, S. Chakrabarti, and L. Isaacs The cucurbit[n]uril family Angew Chem Int Ed 44 31 2005 4844 4870 (Pubitemid 41138666)
2. J.W. Lee, S. Samal, N. Selvapalam, H.J. Kim, and K. Kim Cucurbituril homologues and derivatives: new opportunities in supramolecular chemistry Acc Chem Res 36 8 2003 621 630
3. A.L. Koner, and W.M. Nau Cucurbituril encapsulation of fluorescent dyes Supramol Chem 19 1-2 2007 55 66
4. S. Angelos, N.M. Khashab, Y.W. Yang, A. Trabolsi, H.A. Khatib, and J.F. Stoddart pH clock-operated mechanized nanoparticles J Am Chem Soc 131 36 2009 12912 12914
5. N. Basilio, L. Garcia-Rio, J.A. Moreira, and M. Pessego Supramolecular catalysis by cucurbit[7]uril and cyclodextrins: similarity and differences J Org Chem 75 3 2010 848 855
6. A. Hennig, H. Bakirci, and W.M. Nau Label-free continuous enzyme assays with macrocycle-fluorescent dye complexes Nat Methods 4 8 2007 629 632 (Pubitemid 47202472)
7. D.P. Zou, S. Andersson, R. Zhang, S.G. Sun, B. Akerrnark, and L.C. Sun A host-induced intramolecular charge-transfer complex and light-driven radical cation formation of a molecular triad with cucurbit[8]uril J Org Chem 73 10 2008 3775 3783 (Pubitemid 351671443)
8. J.J. Liu, Y. Xu, X.C. Li, and H. Tian Synthesis and characteristics of a novel pseudorotaxane with the diarylethene as the functional stopper Dyes Pigm 76 1 2008 294 298 (Pubitemid 47034803)
9. I.W. Wyman, and D.H. Macartney Cucurbit[7]uril host-guest complexes with small polar organic guests in aqueous solution Org Biomol Chem 6 10 2008 1796 1801 (Pubitemid 351630367)
10. D. Whang, J. Heo, J.H. Park, and K. Kim A molecular bowl with metal ion as bottom: reversible inclusion of organic molecules in cesium ion complexed cucurbituril Angew Chem Int Ed 37 1-2 1998 78 80
11. J.X. Liu, L.S. Long, R.B. Huang, and L.S. Zheng Interesting anion-inclusion behavior of Cucurbit[5]uril and its lanthanide-capped molecular capsule Inorg Chem 46 24 2007 10168 10173
12. C. Marquez, R.R. Hudgins, and W.M. Nau Mechanism of host-guest complexation by cucurbituril J Am Chem Soc 126 18 2004 5806 5816 (Pubitemid 38621419)
13. R.B. Wang, L. Yuan, and D.H. Macartney A green to blue fluorescence switch of protonated 2-aminoanthracene upon inclusion in cucurbit[7]uril Chem Commun 47 2005 5867 5869 (Pubitemid 43021900)
14. S.P.V. Gromov, I. Artem, G. Kuz'mina Lyudmila, V. Kondratuk Dmitry, K. Sazonov Sergey, A. Strelenko Yuri, V. Alfimov Michael, and A.K. Howard Judith Photocontrolled molecular assembler based on cucurbit[8]uril: [2+2]-Autophotocycloaddition of styryl dyes in the solid state and in water Eur J Org Chem 2010 13 2010 2587 2599
15. J. Mohanty, and W.M. Nau Ultrastable rhodamine with cucurbituril Angew Chem Int Ed 44 24 2005 3750 3754 (Pubitemid 40817197)
16. J. Mohanty, H. Pal, A.K. Ray, S. Kumar, and W.M. Nau Supramolecular dye laser with cucurbit[7]uril in water Chemphyschem 8 1 2007 54 56
17. J. Mohanty, A.C. Bhasikuttan, W.M. Nau, and H. Pal Host-guest complexation of neutral red with macrocyclic host molecules: contrasting pK(a) shifts and binding affinities for cucurbit[7]uril and beta-cyclodextrin J Phys Chem B 110 10 2006 5132 5138
18. M. Megyesi, L. Biczok, and I. Jablonkai Highly sensitive fluorescence response to inclusion complex formation of berberine alkaloid with cucurbit[7]uril J Phys Chem C 112 9 2008 3410 3416 (Pubitemid 351488333)
19. W.M. Nau, and J. Mohanty Taming fluorescent dyes with cucurbituril Int J Photoenerg 7 3 2005 133 141 (Pubitemid 41364585)
20. U. Pischel Chemical approaches to molecular logic elements for addition and subtraction Angew Chem Int Ed 46 22 2007 4026 4040 (Pubitemid 46959914)
21. K. Szacilowski Digital information processing in molecular systems Chem Rev 108 9 2008 3481 3548
22. J. Andreasson, and U. Pischel Smart molecules at work-mimicking advanced logic operations Chem Soc Rev 39 1 2010 174 188
23. U. Pischel, V.D. Uzunova, P. Remon, and W.M. Nau Supramolecular logic with macrocyclic input and competitive reset Chem Commun 46 15 2010 2635 2637
24. S.G. Sun, R. Zhang, S. Andersson, J.X. Pan, B. Akermark, and L.C. Sun The photoinduced long-lived charge-separated state of Ru(bPY)(3)-methylviologen with cucurbit[8]uril in aqueous solution Chem Commun 40 2006 4195 4197 (Pubitemid 44556356)
25. S.G. Sun, S. Andersson, R. Zhang, and L.C. Sun Unusual partner radical trimer formation in a host complex of cucurbit[8]uril, ruthenium(II) tris-bipyridine linked phenol and methyl viologen Chem Commun 46 3 2010 463 465
26. T.Y. Zhang, S.G. Sun, F.Y. Liu, J.L. Fan, Y. Pang, and L.C. Sun Redox-induced partner radical formation and its dynamic balance with radical dimer in cucurbit[8]uril Phys Chem Chem Phys 11 47 2009 11134 11139
27. T.Y. Zhang, S.G. Sun, F.Y. Liu, Y. Pang, J.L. Fan, and X.J. Peng Interaction of DNA and a series of aromatic donor-viologen acceptor molecules with and without the presence of CB[8] Phys Chem Chem Phys 13 20 2011 9789 9795
28. S.G. Sun, W.Y. Gao, F.Y. Liu, F.S. Li, J.L. Fan, and X.J. Peng Redox-induced Ru(bpy)(3)(2+) -methylviologen radical formation and its dimerization in cucurbit[8]uril Phys Chem Chem Phys 13 2 2011 570 575
29. C.V. Kumar, R.S. Turner, and E.H. Asuncion Groove binding of a styrylcyanine dye to the DNA double Helix - the salt effect J Photochem Photobiol A 74 2-3 1993 231 238
30. F. Moyano, S.S. Quintana, R.D. Falcone, J.J. Silber, and N.M. Correa Characterization of multifunctional reverse micelles' interfaces using hemicyanines as molecular probes. I. Effect of the hemicyanines' structure J Phys Chem B 113 13 2009 4284 4292
31. O.A. Fedorova, E.Y. Chernikova, Y.V. Fedorov, E.N. Gulakova, A.S. Peregudov, and K.A. Lyssenko Cucurbit[7]uril complexes of crown-ether derived styryl and (Bis)styryl dyes J Phys Chem B 113 30 2009 10149 10158
32. H.Y. Zhang, Q.C. Wang, M.H. Liu, X. Ma, and H. Tian Switchable V-type [2]pseudorotaxanes Org Lett 11 15 2009 3234 3237
33. A. Day, A.P. Arnold, R.J. Blanch, and B. Snushall Controlling factors in the synthesis of cucurbituril and its homologues J Org Chem 66 24 2001 8094 8100 (Pubitemid 34177959)
34. Y.Y. Huang, T.R. Cheng, F.Y. Li, C.H. Huang, T.J. Hou, and A.C. Yu Photophysical studies on the mono- and dichromophoric hemicyanine dyes I. Photoelectric conversion from the dye modified ITO electrodes J Phys Chem B 106 39 2002 10020 10030
35. D.N. Dybtsev, O.A. Gerasko, A.V. Virovets, M.N. Sokolov, and V.P. Fedin Unexpected guest-controlled formation of two-layered structure in supramolecular adduct of [W3S4(H2O)(9)](4+) and cucurbituril Inorg Chem Commun 3 7 2000 345 349
36. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, and J.R. Cheeseman Gaussian 09, Revision A02 2009 Gaussian, Inc Wallingford CT
37. S. Gadde, E.K. Batchelor, J.P. Weiss, Y.H. Ling, and A.E. Kaifer Control of H- and J-aggregate formation via host-guest complexation using cucurbituril hosts J Am Chem Soc 130 50 2008 17114 17119
38. Y.Y. Huang, T.R. Cheng, F.Y. Li, C.P. Luo, C.H. Huang, and Z.G. Cai Photophysical studies on the mono- and dichromophoric hemicyanine dyes II. Solvent effects and dynamic fluorescence spectra study in chloroform and in LB films J Phys Chem B 106 39 2002 10031 10040
39. J.L. McHale Subpicosecond solvent dynamics in charge-transfer transitions: opportunities in resonance Raman spectroscopy Acc Chem Res 34 4 2001 265 272 (Pubitemid 32816463)
40. X. Cao, R.W. Tolbert, J.L. McHale, and W.D. Edwards Theoretical study of solvent effects on the intramolecular charge transfer of a hemicyanine dye J Phys Chem A 102 17 1998 2739 2748
41. P. Turkewitsch, G.D. Darling, and W.S. Powell Enhanced fluorescence of 4-(p-dimethylaminostyryl)pyridinium salts in the presence of biological macromolecules J Chem Soc Faraday Trans 94 15 1998 2083 2087 (Pubitemid 128758518)
42. W.L. Wang, R. Helgeson, B. Ma, and F. Wudl Synthesis and optical properties of cross-conjugated bis(dimethylaminophenyl)pyridylvinylene derivatives J Org Chem 65 18 2000 5862 5867
43. D.G. Samsonenko, A.V. Virovets, J. Lipkowski, O.A. Geras'ko, and V.P. Fedin Distortion of the cucurbituril molecule by an included 4-methylpyridinum cation J Struct Chem 43 4 2002 664 668 (Pubitemid 36165976)
44. K.A. Connors Binding constants: the measurement of molecular complex Stability 1997 Wiley New York
45. Y.Y. Zhou, H.P. Yu, L. Zhang, J.Y. Sun, L. Wu, and Q. Lu Host properties of cucurbit [7] uril: fluorescence enhancement of acridine orange J Incl Phenom Macrocycl Chem 61 3-4 2008 259 264
46. N. Saleh, A.L. Koner, and W.M. Nau Activation and stabilization of drugs by supramolecular pK(a) shifts: drug-delivery applications tailored for cucurbiturils Angew Chem Int Ed 47 29 2008 5398 5401
47. Y. Kim, H. Kim, Y.H. Ko, N. Selvapalam, M.V. Rekharsky, and Y. Inoue Complexation of aliphatic ammonium ions with a water-soluble cucurbit[6]uril derivative in pure water: isothermal calorimetric, NMR, and X-ray crystallographic study Chem Eur J 15 25 2009 6143 6151
48. J. Mohanty, A.C. Bhasikuttan, S.D. Choudhury, and H. Pal Noncovalent interaction of 5,10,15,20-tetrakis(4-N-methylpyridyl)porphyrin with cucurbit[7]uril: a supramolecular architecture J Phys Chem B 112 35 2008 10782 10785
49. Y.H. Ling, J.T. Mague, and A.E. Kaifer Inclusion complexation of diquat and paraquat by the hosts cucurbit[7]uril and cucurbit[8]uril Chem Eur J 13 28 2007 7908 7914 (Pubitemid 47556367)
50. D. Margulies, G. Melman, and A. Shanzer Fluorescein as a model molecular calculator with reset capability Nat Mater 4 10 2005 768 771 (Pubitemid 41397025)
51. Z.Q. Guo, W.H. Zhu, L.J. Shen, and H. Tian A fluorophore capable of crossword puzzles and logic memory Angew Chem Int Ed 46 29 2007 5549 5553 (Pubitemid 47134541)
52. A. Praetorius, D.M. Bailey, T. Schwarzlose, and W.M. Nau Design of a fluorescent dye for indicator displacement from cucurbiturils: a macrocycle-responsive fluorescent switch operating through a pK(a) shift Org Lett 10 18 2008 4089 4092
53. S.M. Liu, C. Ruspic, P. Mukhopadhyay, S. Chakrabarti, P.Y. Zavalij, and L. Isaacs The cucurbit[n]uril family: prime components for self-sorting systems J Am Chem Soc 127 45 2005 15959 15967 (Pubitemid 41643306)