A pH sensitive and selective ratiometric PAMAM wavelength-shifting bichromophoric system based on PET, FRET and ICT

Dyes and Pigments

Volumn 102, Issue , 2014, Pages 35-45

  Georgiev, Nikolai I ^a   Asiri, Abdullah M ^b   Qusti, Abdullah H ^b   Alamry, Khalid A ^b   Bojinov, Vladimir B ^a,b  

^a UNIVERSITY OF CHEMICAL TECHNOLOGY AND METALLURGY   (Bulgaria)

^b KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

Author keywords

1,8 Naphthalimide; Light harvesting FRET based system; PAMAM dendrimer; Photoinduced electron transfer (PET); Rhodamine 6G; Selective fluorescence pH probes

Indexed keywords

1 , 8-NAPHTHALIMIDE; LIGHT-HARVESTING; PAMAM DENDRIMER; PH PROBE; PHOTO-INDUCED ELECTRON TRANSFER; RHODAMINE 6G;

ENERGY TRANSFER; FLUORESCENCE; PROBES; SENSORS;

ELECTRON TRANSITIONS;

EID: 84887630991     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2013.10.007     Document Type: Article

References (80)

1. A.P. de Silva, D. Fox, A. Huxley, and T. Moody Combining luminescence, coordination and electron transfer for signalling purposes Coord Chem Rev 205 2000 41 57
2. V. Balzani Photochemical molecular devices Photochem Photobiol Sci 2 2003 459 476 (Pubitemid 41655720)
3. R. Badugu, J. Lakowicz, and C. Geddes Cyanide-sensitive fluorescent probes Dye Pigment 64 2005 49 55 (Pubitemid 39033193)
4. M. Jun, B. Roy, and K. Ahn "Turn-on"' fluorescent sensing with "reactive" probes Chem Commun 47 2011 7583 7601
5. 2+displacement approach Tetrahedron 66 2010 1678 1683
6. S. Tal, H. Salman, Y. Abraham, M. Botoshansky, and Y. Eichen Sensitive and selective photoinduced-electron-transfer-based sensing of alkylating agents Chem Eur J 12 2006 4858 4864 (Pubitemid 43954715)
7. N. Marinova, V. Bojinov, and N. Georgiev Design, synthesis and pH sensing properties of novel 1,8-naphtalimide-based bichromophoric system J Photochem Photobiol A Chem 222 2011 132 140
8. H. Dai, and H. Xu A water-soluble 1,8-naphthalimide-based "turn on" fluorescent chemosensor for selective and sensitive recognition of mercury ion in water Bioorg Med Chem Lett 21 2011 5141 5144
9. H. Kim, Z. Guo, W. Zhu, J. Yoon, and H. Tian Recent progress on polymer-based fluorescent and colorimetric chemosensors Chem Soc Rev 40 2011 79 93
10. A.P. de Silva, and S. Uchiyama Molecular logic gates and luminescent sensors based on photoinduced electron transfer Top Curr Chem 300 2011 1 28
11. R. Parkesh, T. Lee, and T. Gunnlaugsson Fluorescence imaging of bone cracks (microdamage) using visibly emitting 1,8-naphthalimide-based PET sensors Tetrahedron Lett 50 2009 4114 4116
12. P. Kaur, S. Kaur, and K. Singh A fluoride selective dipyrromethane-TCNQ colorimetric sensor based on charge-transfer Talanta 84 2011 947 951
13. L. Fabbrizzi, M. Licchelli, P. Pallavicini, A. Perotti, A. Taglietti, and D. Sacchi Fluorescent sensors for transition metals based on electron-transfer and energy-transfer mechanisms Chem Eur J 2 1996 75 82
14. 2+ based on the spirolactam ring-opening process of rhodamine derivatives Bioorg Med Chem 19 2011 1072 1078
15. X. Chen, T. Pradhan, F. Wang, J. Kim, and J. Yoon Fluorescent chemosensors based on spiroring-opening of xanthenes and related derivatives Chem Rev 112 2012 1910 1956
16. W.-S. Li, M.-J. Teng, X.-R. Jia, B.-B. Wang, J.-M. Yeh, and Y. Wei Synthesis and energy-transfer properties of poly(amidoamine) dendrons modified with naphthyl and dansyl groups Tetrahedron Lett 49 2008 1988 1992 (Pubitemid 351265371)
17. N. Georgiev, V. Bojinov, and A. Venkova Design, synthesis and pH sensing properties of novel PAMAM light-harvesting dendrons based on rhodamine 6G and 1,8-naphthalimide J Fluoresc 23 2013 459 471
18. L. Daffy, A.P. de Silva, H. Gunaratne, C. Huber, P. Lynch, and T. Werner Arenedicarboximide building blocks for fluorescent photoinduced electron transfer pH sensors applicable with different media and communication wavelengths Chem Eur J 4 1998 1810 1815 (Pubitemid 28443664)
19. 2+ based on fluorescence resonance energy transfer Dye Pigment 92 2012 909 915
20. S. Zhu, W. Lin, and L. Yuan Development of a ratiometric fluorescent pH probe for cell imaging based on a coumarin-quinoline platform Dye Pigment 99 2013 465 471
21. A. Nantalaksakul, D. Reddy, C. Bardeen, and S. Thayumanavan Light harvesting dendrimers Photosyn Res 87 2006 133 150
22. W.R. Dichtel, S. Hecht, and J. Frèchet Functionally layered dendrimers: a new building block and its application to the synthesis of multichromophoric light-harvesting systems Org Lett 7 2005 4451 4454 (Pubitemid 41436669)
23. R. Mètivier, F. Kulzer, T. Weil, K. Müllen, and T. Basch Energy transfer rates and pathways of single donor chromophores in a multichromophoric dendrimer built around a central acceptor core J Am Chem Soc 126 2004 14364 14365 (Pubitemid 39463614)
24. P. Ceroni, G. Bergamini, F. Marchioni, and V. Balzani Luminescence as a tool to investigate dendrimer properties Prog Polym Sci 30 2005 453 473 (Pubitemid 40654243)
25. O. Flomenboma, R. Amir, D. Shabat, and J. Klaftera Some new aspects of dendrimer applications J Lumin 111 2005 315 325 (Pubitemid 40302965)
26. K. Thomas, A. Thompson, A. Sivakumar, C. Bardeen, and S. Thayumanavan Energy and electron transfer in bifunctional non-conjugated dendrimers J Am Chem Soc 127 2005 373 383 (Pubitemid 40094399)
27. S. Li, W. Zhu, Z. Xu, J. Pan, and H. Tian Antenna-functionalized dendritic β-diketonates and europium complexes: synthetic approaches to generation growth Tetrahedron 62 2006 5035 5048 (Pubitemid 44382416)
28. A. Bar-Haim, and J. Klafter Dendrimers as light harvesting antennae J Lumin 76-77 1998 197 200 (Pubitemid 128390376)
29. V. Bojinov, N. Georgiev, and P. Nikolov Design and synthesis of core and peripherally functionalized with 1,8-naphthalimide units fluorescent PAMAM dendron as light harvesting antenna J Photochem Photobiol A Chem 197 2008 281 289
30. N. Georgiev, V. Bojinov, and P. Nikolov Design and synthesis of a novel pH sensitive core and peripherally 1,8-naphthalimide-labeled PAMAM dendron as light harvesting antenna Dye Pigment 81 2009 18 26
31. N. Georgiev, and V. Bojinov Design, synthesis and photostability of novel 1,8-naphthalimide PAMAM light-harvesting dendrons J Fluoresc 21 2011 51 63
32. I. Grabchev, D. Staneva, V. Bojinov, R. Betcheva, and V. Gregoriou Spectral investigation of coordination of cuprum cations and protons at PAMAM dendrimer peripherally modified with 1,8-naphthalimide units Spectrochim Acta Part A 70 2008 532 536
33. V. Bojinov, N. Georgiev, and P. Nikolov Synthesis and photophysical properties of fluorescence sensing ester- and amidoamine-functionalized 1,8-naphthalimides J Photochem Photobiol A Chem 193 2008 129 138
34. N. Georgiev, and V. Bojinov The design and synthesis of a novel 1,8-naphthalimide PAMAM light-harvesting dendron with fluorescence "off-on" switching core Dye Pigment 84 2010 249 256
35. N. Georgiev, V. Bojinov, and N. Marinova Novel PAMAM light-harvesting antennae based on 1,8-naphthalimide: synthesis, energy transfer, photophysical and pH sensing properties Sens Actuators B Chem 150 2010 655 666
36. T. Konstantinova, and P. Miladinova Synthesis and properties of some fluorescent 1,8-naphthalimide derivatives and their copolymers with methyl methacrylate J Appl Polym Sci 111 2009 1991 1998
37. W. Jin, J. Jiang, X. Wang, X. Zhu, G. Wang, and Y. Song Continuous intra-arterial blood pH monitoring in rabbits with acid-base disorders Respir Physiol Neurobiol 177 2011 183 188
38. V. Bojinov, D. Simeonov, and N. Georgiev A novel blue fluorescent 4-(1,2,2,6,6-pentamethylpiperidin-4-yloxy)-1,8-naphthalimide pH chemosensor based on photoinduced electron transfer Dye Pigment 76 2008 41 46 (Pubitemid 47034770)
39. J. Xie, Y. Chen, W. Yang, D. Xu, and K. Zhang Water soluble 1,8-naphthalimide fluorescent pH probes and their application to bioimagings J Photochem Photobiol A Chem 223 2011 111 118
40. I. Ott, Y. Xu, and X. Qian Fluorescence properties and antiproliferative effects of mono-, bis-, and tris thiophenylnaphthalimides: results of a comparative pilot study J Photochem Photobiol B Biol 105 2011 75 80
41. M. de Souza, R. Correa, V. Filho, I. Grabchev, and V. Bojinov 4-Nitro-1,8-naphthalimides exhibit antinociceptive properties Pharmazie 56 2002 430 431 (Pubitemid 34670182)
42. V. Bojinov, and T. Konstantinova Fluorescent 4-(2,2,6,6- tetramethylpiperidin-4-ylamino)-1,8-naphthalimide pH chemosensor based on photoinduced electron transfer Sens Actuators B Chem 123 2007 869 876 (Pubitemid 46678778)
43. W. Zhu, L. Song, Y. Yang, and H. Tian Novel bisthienylethene containing ferrocenyl-substituted naphthalimide: a photo- and redox multi-addressable molecular switch Chem Eur J 18 2012 13388 13394
44. V. Bojinov, I. Panova, and J.-M. Chovelon Novel blue emitting tetra- and pentamethylpiperidin-4-yloxy-1,8-naphthalimides as photoinduced electron transfer based sensors for transition metal ions and protons Sens Actuators B Chem 135 2008 172 180
45. H. Wang, L. Yang, W. Zhang, Y. Zhou, B. Zhao, and X. Li A colorimetric probe for copper(II) ion based on 4-amino-1,8-naphthalimide Inorg Chim Acta 381 2012 111 116
46. V. Bojinov, I. Panova, D. Simeonov, and N. Georgiev Synthesis and sensor activity of photostable blue emitting 1,8-naphthalimides containing s-triazine UV absorber and HALS fragments J Photochem Photobiol A Chem 210 2010 89 99
47. Y. Wang, X. Zhang, B. Han, J. Peng, S. Hou, and Y. Huang The synthesis and photoluminescence characteristics of novel blue light-emitting naphthalimide derivatives Dye Pigment 86 2010 190 196
48. V. Bojinov, N. Georgiev, and N. Marinova Design and synthesis of highly photostable fluorescence sensing 1,8-naphthalimide-based dyes containing s-triazine UV absorber and HALS units Sens Actuators B Chem 148 2010 6 16
49. V. Bojinov, and I. Panova Novel 4-(2,2,6,6-tetramethylpiperidin-4- ylamino)-1,8-naphthalimide based yellow-green emitting fluorescence sensors for transition metal ions and protons Dye Pigment 80 2009 61 66
50. V. Bojinov, N. Georgiev, and P. Bosch Design and synthesis of highly photostable yellow-green emitting 1,8-naphthalimides as fluorescent sensors for metal cations and protons J Fluoresc 19 2009 127 139
51. N. Georgiev, I. Yaneva, A. Surleva, A.M. Asiri, and V. Bojinov Synthesis, sensor activity and logic behavior of a highly water-soluble naphthalimide derivative Sens Actuators B Chem 184 2013 54 63
52. N. Georgiev, and V. Bojinov Design, synthesis and sensor activity of a highly photostable blue emitting 1,8-naphthalimide J Lumin 132 2012 2235 2241
53. R. Ferreira, P. Remon, and U. Pischel Multivalued logic with a tristable fluorescent switch J Phys Chem C 113 2009 5805 5811
54. N. Georgiev, V. Bojinov, and P. Nikolov Design, synthesis and photophysical properties of two novel 1,8-naphthalimide fluorescent pH sensors based on PET and ICT Dye Pigment 88 2011 350 357
55. N. Georgiev, M. Lyulev, and V. Bojinov Sensor activity and logic behavior of PET based dihydroimidazonaphthalimide diester Spectrochim Acta Part A 97 2012 512 520
56. V. Bojinov, and N. Georgiev Molecular sensors and molecular logic gates [Review] J Univ Chem Technol Metal (Sofia) 46 2011 3 26
57. N. Marinova, N. Georgiev, and V. Bojinov Facile synthesis, sensor activity and logic behaviour of 4-aryloxy substituted 1,8-naphthalimide J Photochem Photobiol A Chem 254 2013 54 61
58. Y. Sun, S. Wei, C. Yin, La Liu, Ci Hu, and Y. Zhao Synthesis and spectroscopic characterisation of 4-butoxyethoxy-N-octadecyl-1,8-naphthalimide as a new fluorescent probe for the determination of proteins Bioorg Med Chem Lett 21 2011 3798 3804
59. M. Dong, T.-H. Ma, A.-J. Zhang, Y.-M. Dong, Y.-W. Wang, and Y. Peng A series of highly sensitive and selective fluorescent and colorimetric "off-on" chemosensors for Cu (II) based on rhodamine derivatives Dye Pigment 87 2010 164 172
60. 2+ based on a rhodamine-coumarin conjugate Anal Chim Acta 663 2010 85 90
61. B. Ahamed, and P. Ghosh An integrated system of pyrene and Rhodamine-6G for selective colorimetric and fluorometric sensing of mercury(II) Inorg Chim Acta 372 2011 100 107
62. Y. Lei, Y. Su, and J. Huo Photophysical property of rhodamine-cored poly(amidoamine) dendrimers: simultaneous effect of spirolactam ring-opening and PET process on sensing trivalent chromium ion J Lumin 131 2011 2521 2527
63. H.-S. Lv, J. Liu, J. Zhao, B.-X. Zhao, and J.-Y. Miao Highly selective and sensitive pH-responsive fluorescent probe in living hela and HUVEC cells Sens Actuators B Chem 177 2013 956 963
64. H. Zhu, J. Fan, Q. Xu, H. Li, J. Wang, and P. Gao Imaging of lysosomal pH changes with a fluorescent sensor containing a novel lysosome-locating group Chem Commun 48 2012 11766 11768
65. H. Li, H. Guan, X. Duan, J. Hu, G. Wang, and Q. Wang An acid catalyzed reversible ring-opening/ring-closure reaction involving a cyano-rhodamine spirolactam Org Biomol Chem 11 2013 1805 1809
66. V. Bojinov, A. Venkova, and N. Georgiev Synthesis and energy-transfer properties of fluorescence sensing bichromophoric system based on Rhodamine 6G and 1,8-naphthalimide Sens Actuators B Chem 143 2009 42 49
67. H.-S. Lv, S.-Y. Huang, B.-X. Zhao, and J.-Y. Miao A new rhodamine B-based lysosomal pH fluorescent indicator Anal Chim Acta 788 2013 177 182
68. 2 composites functionalized with spirolactam-based molecular switch J Colloid Interface Sci 406 2013 178 185
69. 3+ based on rhodamine-cored poly(amidoamine) dendrimer Spectrochim Acta Part A 81 2011 149 154
70. I. Grabchev, I. Moneva, V. Bojinov, and S. Guittonneau Synthesis and properties of fluorescent 1,8-naphthalimide dyes for application in liquid crystal displays J Mater Chem 10 2000 1291 1296
71. R. Kubin, and A. Fletcher Fluorescence quantum yields of some rhodamine dyes J Lumin 27 1982 455 462 (Pubitemid 13505734)
72. G. Reynolds, and K. Drexhage New coumarin dyes with rigidized structure for flashlamp-pumped dye lasers Opt Commun 13 1975 222 225
73. C. Niu, G. Zeng, L. Chen, G. Shena, and R. Yu Proton "off-on" behaviour of methylpiperazinyl derivative of naphthalimide: a pH sensor based on fluorescence enhancement Analyst 129 2004 20 24 (Pubitemid 38130296)
74. J. Gan, K. Chen, C. Chang, and H. Tian Luminescent properties and photo-induced electron transfer of naphthalimides with piperazine substituent Dye Pigment 57 2003 21 28 (Pubitemid 36380619)
75. V. Bojinov, and I. Panova Synthesis and absorption properties of new yellow-green emitting benzo[de]isoquinoline-1,3-diones containing hindered amine and 2-hydroxyphenylbenzotriazole fragments Dye Pigment 74 2007 551 560 (Pubitemid 46323345)
76. S. Bakkialakshmi, and T. Menaka A study of the interaction between rhodamine 6G and hydroxy propyl β-cyclodextrin by steady state fluorescence Spectrochim Acta Part A 81 2011 8 13
77. M. Zakerhamidi, M. Moghadam, A. Ghanadzadeh, and S. Hosseini Anisotropic and isotropic solvent effects on the dipole moment and photophysical properties of rhodamine dyes J Lumin 132 2012 931 937
78. J. Fortier, P. Even-Hernandez, F. Baros, S. Poulain, N. Martinet, and M. Donner The synthesis, photophysical properties and energy transfer of a coumarin-based bichromophoric compound Dye Pigment 80 2009 115 120
79. N. Georgiev, A. Sakr, and V. Bojinov Design and synthesis of novel fluorescence sensing perylene diimides based on photoinduced electron transfer Dye Pigment 91 2011 332 339
80. J. Liu, and A.P. de Silva Path-selective photoinduced electron transfer (PET) in a membrane-associated system studied by pH-dependent fluorescence Inorg Chim Acta 381 2012 243 246