A multiple switching diarylethene with a phenyl-linked rhodamine B unit and its application as chemosensor for Cu2+

Dyes and Pigments

Volumn 113, Issue , 2015, Pages 70-77

  Pu, Shouzhi ^a   Ma, Lele ^a   Liu, Gang ^a   Ding, Haichang ^a   Chen, Bing ^a  

^a JIANGXI SCIENCE AND TECHNOLOGY NORMAL UNIVERSITY   (China)

Author keywords

Diarylethene; Dual fluorescence switch; INHIBIT logic gate; Phenyl linked rhodamine B unit; Photochromism

Indexed keywords

LOGIC GATES; PHOTOCHROMISM; PHYSIOLOGY;

AQUEOUS ACETONITRILE; DIARYLETHENES; DUAL FLUORESCENCE; FLUORESCENCE INTENSITIES; FLUORESCENCE SWITCH; RATIOMETRIC; RHODAMINE B; SEQUENTIAL STIMULATION; CHEMOSENSOR; ITS APPLICATIONS; MULTIPLE SWITCHING;

FLUORESCENCE; PHOTOCHROMISM;

EID: 84906673416     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2014.07.030     Document Type: Article

References (56)

1. N. Fuentes, A. Martín-Lasanta, L.Á. de Cienfuegos, M. Ribagorda, A. Parraa, and J.M. Cuerva Organic-based molecular switches for molecular electronics Nanoscale 3 2011 4003 4014
2. N. Weibel, S. Grunder, and M. Mayor Functional molecules in electronic circuits Org Biomol Chem 5 2007 2343 2353 (Pubitemid 47118867)
3. J. Andreasson, and U. Pischel Smart molecules at work-mimicking advanced logic operations Chem Soc Rev 39 2010 174 188
4. 2+ ions or water Dyes Pigms 111 2014 1 7
5. B.L. Feringa Molecular switches 2001 Wiley-VCH Weinheim, Germany
6. Z.Q. Guo, W.H. Zhu, Y.Y. Xiong, and H. Tian Multiple logic fluorescent thermometer system based on N-isopropylmethacrylamide copolymer bearing dicyanomethylene-4H-pyran moiety Macromolecules 42 2009 1448 1453
7. J.S. Kim, and D.T. Quang Calixarene-derived fluorescent probes Chem Rev 107 2007 3780 3799 (Pubitemid 47541850)
8. 2+-driven AND logic operations Chem Commun 2004 2048 2049 (Pubitemid 39389506)
9. Y. Shiraishi, Y. Tokitoh, G. Nishimura, and T. Hirai A molecular switch with pH-controlled absolutely switchable dual-mode fluorescence Org Lett 7 2005 2611 2614 (Pubitemid 43034220)
10. K.W. Cheng, C.C. Lai, P.T. Chiang, and S.H. Chiu Reading the operation of an acid/base-controllable molecular switch by naked eye Chem Commun 2006 2854 2856
11. S. Uchiyama, N. Kawai, A.P. de Silva, and K. Iwai Fluorescent polymeric and logic gate with temperature and pH as inputs J Am Chem Soc 126 2004 3032 3033 (Pubitemid 38380693)
12. J.J. Zhang, Q. Zou, and H. Tian Photochromic materials: more than meets the eye Adv Mater 25 2013 378 399
13. G. Zhang, D. Zhang, X. Guo, and D. Zhu A new redox-fluorescence switch based on a triad with tetrathiafulvalene and anthracene units Org Lett 6 2004 1209 1212 (Pubitemid 38692025)
14. S.A. de Silva, B. Amorelli, D.C. Isidor, K.C. Loo, K.E. Crooker, and Y.E. Pena A fluorescent 'off-on-off' proton switch with an overriding 'enable-disable' sodium ion switch Chem Commun 2002 1360 1361 (Pubitemid 34651803)
15. J.J. Zhang, W.J. Tan, X.L. Meng, and H. Tian Soft mimic gear-shift with a multi-stimulus modified diarylethene J Mater Chem 19 2009 5726 5729
16. + ions by or from a photoisomerizable monolayer-modified electrode Langmuir 27 2011 1380 1386
17. Y. Wang, and Q. Li Light-driven chiral molecular switches or motors in liquid crystals Adv Mater 24 2012 1926 1945
18. B.L. Feringa, R.A. van Delden, N. Koumura, and E.M. Geertsema Chiroptical molecular switches Chem Rev 100 2000 1789 1816
19. M. Bossi, V. Belov, S. Polyakova, and S.W. Hell Reversible red fluorescent molecular switches Angew Chem Int Ed 45 2006 7462 7465 (Pubitemid 44786986)
20. I. Yildiz, S. Impellizzeri, E. Deniz, B. McCaughan, J.F. Callan, and F.M. Raymo Supramolecular strategies to construct biocompatible and photoswitchable fluorescent assemblies J Am Chem Soc 133 2011 871 879
21. T. Fukaminato, T. Sasaki, T. Kawai, N. Tamai, and M. Irie Digital photoswitching of fluorescence based on the photochromism of diarylethene derivatives at a single-molecule level J Am Chem Soc 126 2004 14843 14849 (Pubitemid 39532165)
22. P.A. Liddell, G. Kodis, A.L. Moore, T.A. Moore, and D. Gust Photonic switching of photoinduced electron transfer in a dithienylethene-porphyrin- fullerene triad molecule J Am Chem Soc 124 2002 7668 7669 (Pubitemid 34733774)
23. V.W.W. Yan, C.C. Ko, and N. Zhu Photochromic and luminescence switching properties of a versatile diarylethene-containing 1,10-phenanthroline ligand and its rhenium(I) complex J Am Chem Soc 126 2004 12734 12735 (Pubitemid 39372277)
24. T.A. Golovkova, D.V. Kozlov, and D.C. Neckers Synthesis and properties of novel fluorescent switches J Org Chem 70 2005 5545 5549 (Pubitemid 40980763)
25. M. Irie, O. Miyatake, and K. Uchida Blocked photochromism of diarylethenes J Am Chem Soc 114 1992 8715 8716
26. A. Peters, and N.R. Branda Electrochromism in photochromic dithienylcyclopentenes J Am Chem Soc 125 2003 3404 3405 (Pubitemid 36512395)
27. Y. Moriyama, K. Matsuda, N. Tanifuji, S. Irie, and M. Irie Electrochemical cyclization/cycloreversion reactions of diarylethenes Org Lett 7 2005 3315 3318 (Pubitemid 41059133)
28. N. Tanifuji, M. Irie, and K. Matsuda New photoswitching unit for magnetic interaction: diarylethene with 2,5-bis(arylethynyl)-3-thienyl group J Am Chem Soc 127 2005 13344 13353 (Pubitemid 41377631)
29. T.J. Wigglesworth, D. Sud, T.B. Norsten, V.S. Lekhi, and N.R. Branda Chiral discrimination in photochromic helicenes J Am Chem Soc 127 2005 7272 7273 (Pubitemid 40745989)
30. D. Sud, T.B. Norsten, and N.R. Branda Photoswitching of stereoselectivity in catalysis using a copper dithienylethene complex Angew Chem Int Ed 44 2005 2019 2021 (Pubitemid 40483025)
31. M. Irie Diarylethenes for memories and switches Chem Rev 100 2000 1685 1716
32. H. Tian, and S.J. Yang Recent progresses on diarylethene based photochromic switches Chem Soc Rev 33 2004 85 97 (Pubitemid 38388007)
33. Q. Zou, J.J. Zhang, and H. Tian Multi-functional molecular switches based on photochromic dithienylethenes Prog Chem 24 2012 1632 1645
34. H.B. Cheng, H.Y. Zhang, and Y. Liu Dual-stimulus luminescent lanthanide molecular switch based on an unsymmetrical diarylperfluorocyclopentene J Am Chem Soc 135 2013 10190 10193
35. N. Soh, K. Yoshida, H. Nakajima, K. Nakano, T. Imato, and T. Fukaminato et al. A fluorescent photochromic compound for labeling biomolecules Chem Commun 2007 5206 5208 (Pubitemid 350222814)
36. T. Fukaminato, T. Doi, N. Tamaoki, K. Okuno, Y. Ishibashi, and H. Miyasaka et al. Single-Molecule fluorescence photoswitching of a diarylethene-perylenebisimide dyad: non-destructive fluorescence readout J Am Chem Soc 133 2011 4984 4990
37. W.J. Tan, X. Li, J.J. Zhang, and H. Tian A photochromic diarylethe ne dyad based on perylene diimide Dyes Pigm 89 2011 260 265
38. Y.M. Yang, Q. Zhao, W. Feng, and F.Y. Li Luminescent chemodosimeters for bioimaging Chem Rev 113 2013 192 270
39. X.Q. Chen, T. Pradhan, F. Wang, J.S. Kim, and J. Yoon Fluorescent chemosensors based on spiroring-opening of xanthenes and related derivatives Chem Rev 112 2012 1910 1956
40. W.J. Liu, S.Z. Pu, D.H. Jiang, S.Q. Cui, G. Liu, and C.B. Fan Fluorescent probes for Al(III) and Cr(III) based on a photochromic diarylethene bearing a fluorescent rhodamine unit Microchim Acta 174 2011 329 336
41. S.Z. Pu, D.H. Jiang, W.J. Liu, G. Liu, and S.Q. Cui Multi-addressable molecular switches based on photochromic diarylethenes bearing a rhodamine unit J Mater Chem 22 2012 3517 3526
42. S.Z. Pu, H.C. Ding, G. Liu, C.H. Zheng, and H.Y. Xu Multiaddressing fluorescence switch based on a new photochromic diarylethene with a triazole-linked rhodamine B unit J Phys Chem C 118 2014 7010 7017
43. 2+ based on a new diarylethene with a stilbene-linked terpyridine unit Dyes Pigm 107 2014 38 44
44. H. Tian, and S. Wang Photochromic bisthienylethene as multi-function switches Chem Commun 2007 781 792
45. S.C. Pang, H. Hyun, S. Lee, D. Jang, M.J. Lee, and S.H. Kang et al. Photoswitchable fluorescent diarylethene in a turn-on mode for live cell imaging Chem Commun 48 2012 3745 3747
46. H.Y. Zheng, W.D. Zhou, M.J. Yuan, X.D. Yin, Z.C. Zuo, and C.B. Ouyang et al. Optic and proton dual-control of the fluorescence of rhodamine based on photochromic diarylethene: mimicking the performance of an integrated logic gate Tetrahedron Lett 50 2009 1588 1592
47. L. Yuan, W.Y. Lin, Z.M. Cao, J.L. Wang, and B. Chen Development of FRET-based dual-excitation ratiometric fluorescent pH probes and their photocaged derivatives Chem Eur J 18 2012 1247 1255
48. N.B. Yapici, S.R. Mandalapu, T.L. Chew, S. Khuon, and L.R. Bi Determination of intracellular pH using sensitive, clickable fluorescent probes Bioorg Med Chem Lett 22 2012 2440 2443
49. 2+ Sens Actuators B 161 2012 948 953
50. N. Wanichacheva, K. Setthakarn, N. Prapawattanapol, O. Hanmeng, V.S. Lee, and K. Grudpan Rhodamine B-based "turn-on" fluorescent and colorimetric chemosensors for highly sensitive and selective detection of mercury (II) ions J Lumin 132 2012 35 40
51. 2+-selective fluorescent probe derived from rhodamine B Dyes Pigm 96 2013 38 44
52. 2+) sensor and its application in the biological system Dyes Pigm 92 2012 1083 1090
53. 2+ chemodosimeters and the applications for living cell imaging Org Lett 14 2012 432 435
54. 3+ through time-dependent PET-CHEF-FRET processes and its cell staining application Inorg Chem 52 2013 3627 3633
55. 2+ in aqueous solution and living cells Anal Chem 81 2009 7022 7030
56. 2+ and its application in live cell imaging Sens Actuators B 162 2012 313 320