Fluorescent and colorimetric chemosensors for cations based on 1,8-naphthalimide derivatives: Design principles and optical signalling mechanisms

Russian Chemical Reviews

Volumn 83, Issue 2, 2014, Pages 155-182

  Panchenko, P A ^a   Fedorova, O A ^a   Fedorov, Yu V ^a  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84897584271     PISSN: 0036021X     EISSN: 14684837     Source Type: Journal    
DOI: 10.1070/RC2014v083n02ABEH004380     Document Type: Review

References (172)

1. Trace Analysis: Spectroscopic Methods for Elements (Ed. J Winefordner) (New York: Wiley, 1976)
2. B Valeur Molecular Fluorescence. Principles and Applications (Weinheim: Wiley-VCH, 2006)
3. A P de Silva, H Q N Gunaratne, T Gunnlaugsson, A J M Huxley, C P McCoy, J T Rademacher, T E Rice Chem. Rev. 97 1515 (1997)
4. R Martínez-Máñez, F Sanceó n Chem. Rev. 103 4419 (2003)
5. J F Callan, A P de Silva, D C Magri Tetrahedron 61 8551 (2005)
6. T Gunnlaugsson, M Glynn, G M Tocci, P E Kruger, F M Pfeffer Coord. Chem. Rev. 250 3094 (2006)
7. I Grabchev, T Konstantinova Dyes Pigm. 33 197 (1997)
8. E Martin, R Weigand, A Pardo J. Lumin. 68 157 (1996)
9. C Siegers, B OlaÁ h, U Wü rfel, J Hohl-Ebinger, A Hinsch, R Haag Solar Energ. Mater. Solar Cells 93 552 (2009)
10. H-H Lin, Y-C Chan, J-W Chen, C-C Chang J. Mater. Chem. 21 3170 (2011)
11. G Tu, Q Zhou, Y Cheng, Y Geng, L Wang, D Ma, X Jing, F Wang Synth. Met. 152 233 (2005)
12. Z Li, Q Yang, X Qian Bioorg. Med. Chem. 13 4864 (2005)
13. B May, X Poteau, D Yuan, R G Brown Dyes Pigm. 42 79 (1999)
14. D W Cho, M Fujitsuka, A Sugimoto, T Majima J. Phys. Chem. A 112 7208 (2008)
15. D W Cho, M Fujitsuka, U C Yoon, T Majima J. Photochem. Photobiol., A 190 101 (2007)
16. T P Le, J E Rogers, L A Kelly J. Phys. Chem. A 104 6778 (2000)
17. D W Cho, M Fujitsuka, A Sugimoto, U C Yoon, P S Mariano, T Majima J. Phys. Chem. B 110 11062 (2006)
18. M D McKenna, I Grabchev, P Bosch Dyes Pigm. 81 180 (2009)
19. L Song, E A Jares-Erijman, T M Jovin J. Photochem. Photobiol., A 150 177 (2002)
20. J L Magalhä es, R V Pereira, E R Triboni, P B Filho, M H Gehlen, F C Nart J. Photochem. Photobiol., A 183 165 (2006)
21. D Yuan, R G Brown, J D Hepworth, M S Alexiou, J H P Tyman J. Heterocycl. Chem. 45 397 (2008)
22. S Saha, A Samanta J. Phys Chem. A 106 4763 (2002)
23. S Brochsztain, M A Rodrigues, M J Politi J. Photochem. Photobiol., A 107 195 (1997)
24. X Meng, W Zhu, Q Zhang, Y Feng, W Tan, H Tian J. Phys. Chem. B 112 15636 (2008)
25. L Song, Y Yang, Q Zhang, H Tian, W Zhu J. Phys. Chem. B 115 14648 (2011)
26. R M Duke, E B Veale, F M Pfeffer, P E Kruger, T Gunnlaugsson Chem. Soc. Rev. 39 3936 (2010)
27. M Oelgemö ller, W H Kramer J. Photochem. Photobiol., C 11 210 (2010)
28. M Lv, H Xu Curr. Med. Chem. 16 4797 (2009)
29. L Ingrassia, F Lefranc, R Kiss, T Mijatovic Curr. Med. Chem. 16 1192 (2009)
30. S Banerjee, E B Veale, C M Phelan, S A Murphy, G M Tocci, L J Gillespie, D O Frimannsson, J M Kelly, T Gunnlaugsson Chem. Soc. Rev. 42 1601 (2013)
31. Y Jeong, J Yoon Inorg. Chim. Acta 381 2 (2012)
32. M Formica, V Fusi, L Giorgi, M Micheloni Coord. Chem. Rev. 256 170 (2012)
33. R A Bissell, A P de Silva, H Q N Gunaratne, P L M Lynch, G E M Maguire, C P McCoy, K R A S Sandanayake Top. Curr. Chem. 168 223 (1993)
34. A P de Silva, D B Fox, A J M Huxley, T S Moody Coord. Chem. Rev. 205 41 (2000)
35. A P de Silva, T S Moody, G D Wright Analyst 134 2385 (2009)
36. R Bergonzi, L Fabbrizzi, M Licchelli, C Mangano Coord. Chem. Rev. 170 31 (1998)
37. A P Demchenko Lab Chip 5 1210 (2005)
38. I L Belaits, R N Nurmukhametov, D N Shigorin Zh. Fiz. Khim. 43 869 (1969)
39. N V Korol'kova, G A Val'kova, D N Shigorin, V A Shigalevskii, V N Vostrova Zh. Fiz. Khim. 64 393 (1990)
40. V Wintgens, P Valat, J Kossanyi J. Chem. Soc., Faraday Trans. 90 411 (1994)
41. R N Nurmukhametov, L I Semenova, N V Korol'kova, G A Val'kova, I I Ponomarev Zh. Fiz. Khim. 64 2972 (1990)
42. R N Nurmukhametov Pogloshchenie i Lyuminestsentsiya Aromaticheskikh Soedinenii (Absorption and Luminescence of Aromatic Compounds) (Moscow: Khimiya, 1971)
43. A Demeter, T Bé rces, L Biczdk J. Phys. Chem. 100 2001 (1996)
44. A Bigotto, V Galasso, G Distefano, A Modelli J. Chem. Soc., Perkin Trans. 2 1502 (1979)
45. M S Alexiou, V Tychopoulos, S Ghorbanian, J H P Tyman, R G Brown, P I Brittain J. Chem. Soc., Perkin Trans. 2 837 (1990)
46. V G Mitina, V V Ivanov, O A Ponomarev, L A Sleta Mol. Eng. 6 249 (1996)
47. L D Patsenker, Y Ye Artyukhova J. Mol. Struct. 655 311 (2003)
48. P Kucheryavy, G Li, S Vyas, C Hadad, K D Glusac J. Phys. Chem. A 113 6453 (2009)
49. H Shaki, K Gharanjig, S Rouhani, A Khosravi J. Photochem. Photobiol., A 216 44 (2010)
50. I Grabchev Dyes Pigm. 38 219 (1998)
51. G J-F Demets, E R Triboni, E B Alvarez, G M Arantes, P B Filho, M J Politi Spectrochim. Acta, Part A 63 220 (2006)
52. E Martin, J L G Coronado, J J Camacho, A Pardo J. Photochem. Photobiol., A 175 1 (2005)
53. K Rurack, U Resch-Genger, J L Bricks, M Spieles Chem. Commun. 2103 (2000)
54. B Bian, S-J Ji, H-B Shi Dyes Pigm. 76 348 (2008)
55. H Cao, V Chang, R Hernandez, M D Heagy J. Org. Chem. 70 4929 (2005)
56. P Nandhikonda, M P Begaye, Z Cao, M D Heagy Chem. Commun. 4941 (2009)
57. S Paudel, P Nandhikonda, M D Heagy J. Fluoresc. 19 681 (2009)
58. P Nandhikonda, M P Begaye, Z Cao, M D Heagy Org. Biomol. Chem. 8 3195 (2010)
59. Z Li, Q Yang, R Chang, G Ma, M Chen, W Zhang Dyes Pigm. 88 307 (2011)
60. P Nandhikonda, S Paudel, M D Heagy Tetrahedron 65 2173 (2009)
61. A P de Silva, H Q N Gunaratne, J-L Habib-Jiwan, C P McCoy, T E Rice, J-P Soumillion Angew. Chem., Int. Ed. Engl. 34 1728 (1995)
62. A P de Silva, T E Rice Chem. Commun. 163 (1999)
63. Y Q Gao, R A Marcus J. Phys. Chem. A 106 1956 (2002)
64. J Gan, K Chen, C-P Chang, H Tian Dyes Pigm. 57 21 (2003)
65. I Grabchev, S Sali, R Betcheva, V Gregoriou Eur. Polym. J. 43 4297 (2007)
66. O Kreft, A M Javier, G B Sukhorukov, W J Parak J. Mater. Chem. 17 4471 (2007)
67. C-G Niu, Z-Z Li, X-B Zhang, W-Q Lin, G-L Shen, R-Q Yu Anal. Bioanal. Chem. 372 519 (2002)
68. I Grabchev, J-M Chovelon Dyes Pigm. 77 1 (2008)
69. I Grabchev, S Dumas, J-M Chovelon Polym. Adv. Technol. 19 316 (2008)
70. I Grabchev, X Qian, Y Xiao, R Zhang New J. Chem. 26 920 (2002)
71. A Schulz, J Wotschadlo, T Heinze, G J Mohr J. Mater. Chem. 20 1475 (2010)
72. T Doussineau, S Trupp, G J Mohr J. Colloid Interface Sci. 339 266 (2009)
73. L Xu, Y Xu, W Zhu, C Yang, L Han, X Qian Dalton Trans. 41 7212 (2012)
74. C-Y Li, F Xu, Y-F Li, K Zhou, Y Zhou Anal. Chim. Acta 717 122 (2012)
75. X Guo, X Qian, L Jia J. Am. Chem. Soc. 126 2272 (2004)
76. C He, W Zhu, Y Xu, T Chen, X Qian Anal. Chim. Acta 651 227 (2009)
77. B Ramachandram, A Samanta Chem. Commun. 1037 (1997)
78. Z Liu, C Zhang, X Wang, W He, Z Guo Org. Lett. 14 4378 (2012)
79. P Ghos, P K Bharadwaj, S Mandal, S Ghosh J. Am. Chem. Soc. 118 1553 (1996)
80. S Banthia, A Samanta J. Phys. Chem. B 106 5572 (2002)
81. B Ramachandram, N B Sankaran, R Karmakar, S Saha, A Samanta Tetrahedron 56 7041 (2000)
82. B Ramachandram, G Saroja, N B Sankaran, A Samanta J. Phys. Chem. B 104 11824 (2000)
83. B Ramachandram J. Fluoresc. 15 71 (2005)
84. G-T Wen, M-Z Zhu, Z Wang, X-M Meng, H-Y Hu, Q-X Guo Chin. J. Chem. 24 1230 (2006)
85. Z Xu, S J Han, C Lee, J Yoon, D R Spring Chem. Commun. 46 1679 (2010)
86. Z Xu, K-H Beak, H N Kim, J Cui, X Qian, D R Spring, I Shin, J Yoon J. Am. Chem. Soc. 132 601 (2009)
87. Z Xu, S Zheng, J Yoon, D R Spring Analyst 135 2554 (2010)
88. J Fan, X Peng, Y Wu, E Lu, J Hou, H Zhang, R Zhang, X Fu J. Lumin. 114 125 (2005)
89. J Wang, Y Xiao, Z Zhang, X Qian, Y Yang, Q Xu J. Mater. Chem. 15 2836 (2005)
90. T Gunnlaugsson, T C Lee, R Parkesh Org. Biomol. Chem. 1 3265 (2003)
91. R Parkesh, T C Lee, T Gunnlaugsson Org. Biomol. Chem. 5 310 (2007)
92. S Lee, J H Lee, T Pradhan, C S Lim, B R Cho, S Bhuniya, S Kim, J S Kim Sens. Actuators, B 160 1489 (2011)
93. J W Steed, J L Atwood Supramolecular Chemistry (Chichester: Wiley, 2000)
94. I Grabchev, D Staneva, R Betcheva Polym. Degrad. Stab. 91 2257 (2006)
95. I Grabchev, J-M Chovelon, V Bojinov, G Ivanova Tetrahedron 59 9591 (2003)
96. S-P Yang, L Lin, L-Z Yang, J-M Chen, Q-Q Chen, D Cao, X-B Yu J. Lumin. 126 515 (2007)
97. S Sali, I Grabchev, J-M Chovelon, G Ivanova Spectrochim. Acta, Part A 65 591 (2006)
98. I Grabchev, S Guittonneau J. Photochem. Photobiol., A 179 28 (2006)
99. I Grabchev, P Bosch, M McKenna, D Staneva J. Photochem. Photobiol., A 201 75 (2009)
100. P A Panchenko, Y V Fedorov, O A Fedorova, G Jonusauskas Dyes Pigm. 98 347 (2013)
101. P A Panchenko, Y V Fedorov, O A Fedorova, B A Izmailov, V A Vasnev, V V Istratov, E A Makeeva, M N Rumyantseva, A M Gaskov Mendeleev Commun. 21 12 (2011)
102. H He, M A Mortellaro, M J P Leiner, S T Young, R J Fraatz, J K Tusa Anal. Chem. 75 549 (2003)
103. H He, M A Mortellaro, M J P Leiner, R J Fraatz, J K Tusa J. Am. Chem. Soc. 125 1468 (2003)
104. X Zhou, F Su, W Gao, Y Tian, C Youngbull, R H Johnson, D R Meldrum Biomaterials 32 8574 (2011)
105. P Nandhikonda, M P Begaye, M D Heagy Tetrahedron Lett. 50 2459 (2009)
106. T Chen, W Zhu, Y Xu, S Zhang, X Zhang, X Qian Dalton Trans. 39 1316 (2010)
107. J L Bricks, A Kovalchuk, C Trieflinger, M Nofz, M Bü schel, A I Tolmachev, J Daub, K Rurack J. Am. Chem. Soc. 127 13522 (2005)
108. A N Sergeeva, P A Panchenko, Y V Fedorov, O A Fedorova Prot. Met. Phys. Chem. Surf. 48 524 (2012)
109. [Fizikokh. Poverkhn. Zashch. Mater. 48 440 (2012)]
110. E Tamanini, A Katewa, L M Sedger, M H Todd, M Watkinson Inorg. Chem. 48 319 (2009)
111. E Tamanini, K Flavin, M Motevalli, S Piperno, L A Gheber, M H Todd, M Watkinson Inorg. Chem. 49 3789 (2010)
112. H Mu, R Gong, Q Ma, Y Sun, E Fu Tetrahedron Lett. 48 5525 (2007)
113. H Wang, L Yang, W Zhang, Y Zhou, B Zhao, X Li Inorg. Chim. Acta 381 111 (2012)
114. H Wang, H Wu, L Xue, Y Shi, X Li Org. Biomol. Chem. 9 5436 (2011)
115. K Hanaoka, Y Muramatsu, Y Urano, T Terai, T Nagano Chem. - Eur. J. 16 568 (2010)
116. F Cosnard, V Wintgens Tetrahedron Lett. 39 2751 (1998)
117. C Hou, A M Urbanec, H Cao Tetrahedron Lett. 52 4903 (2011)
118. L Duan, Y Xu, X Qian Chem. Commun. 6339 (2008)
119. Z Xu, X Qian, J Cui Org. Lett. 7 3029 (2005)
120. Z Xu, Y Xiao, X Qian, J Cui, D Cui Org. Lett. 7 889 (2005)
121. W Wang, Q Yang, L Sun, H Wang, C Zhang, X Fei J. Hazard. Mater. 194 185 (2011)
122. Z Xu, J Pan, D R Spring, J Cui, J Yoon Tetrahedron 66 1678 (2010)
123. J Huang, Y Xu, X Qian Org. Biomol. Chem. 7 1299 (2009)
124. Z Xu, X Qian, J Cui, R Zhang Tetrahedron 62 10117 (2006)
125. Z Xu, S Kim, H N Kim, S J Han, C Lee, J S Kim, X Qian, J Yoon Tetrahedron Lett. 48 9151 (2007)
126. J Huang, Y Xu, X Qian Dalton Trans. 1761 (2009)
127. P Comba, W Goll, B Nuber, K Vá rnagy Eur. J. Inorg. Chem. 2041 (1998)
128. R Benshafrut, A Haran, D Shvarts, B Schneider J. Org. Chem. 67 4040 (2002)
129. B Liu, H Tian Chem. Commun. 3156 (2005)
130. B Leng, L Zou, J Jiang, H Tian Sens. Actuators, B 140 162 (2009)
131. C Li, S Liu J. Mater. Chem. 20 10716 (2010)
132. R K Jackson, Y Shi, X Yao, S C Burdette Dalton Trans. 39 4155 (2010)
133. D Cui, X Qian, F Liu, R Zhang Org. Lett. 6 2757 (2004)
134. H Sharma, N Kaur, N Singh Inorg. Chim. Acta 391 83 (2012)
135. J R Lakowicz Principles of Fluorescent Spectroscopy (New York: Kluwer Academic, Plenum, 1999)
136. J Brumbaugh, A Schleifenbaum, G Stier, M Sattler, C Schultz Nat. Protoc. 1 1044 (2006)
137. I A Demarco, A Periasami, C F Booker, R N Day Nat. Methods 3 519 (2006)
138. H Wallrabe, A Periasamy Curr. Opin. Biotechnol. 16 19 (2005)
139. H Yu, M Fu, Y Xiao Phys. Chem. Chem. Phys. 12 7386 (2010)
140. A Coskun, E U Akkaya J. Am. Chem. Soc. 127 10464 (2005)
141. I Grabchev, P Bosch, D Staneva J. Photochem. Photobiol., A 222 288 (2011)
142. B M Krasovitskii, T P Zubanova, Yu M Vinetskaya Chem. Heterocycl. Compd. 18 964 (1982)
143. [Khim. Geterotsikl. Soedin. 1248 (1982)]
144. C-M Bouché, P Le Barny, H Facoetti, P Robin Appl. Phys. Lett. 73 879 (1998)
145. N I Georgiev, V B Bojinov, P S Nikolov Dyes Pigm. 81 18 (2009)
146. X Zhou, F Su, H Lu, P Senechal-Willis, Y Tian, R H Johnson, D R Meldrum Biomaterials 33 171 (2012)
147. B H Shankar, D Ramaiah J. Phys. Chem. B 115 13292 (2011)
148. V S Jisha, A J Thomas, D Ramaiah J. Org. Chem. 74 6667 (2009)
149. S Abad, M Kluciar, M A Miranda, U Pischel J. Org. Chem. 70 10565 (2005)
150. V B Bojinov, A I Venkova, N I Georgiev Sens. Actuators, B 143 42 (2009)
151. Z Zhou, M Yu, H Yang, K Huang, F Li, T Yi, C Huang Chem. Commun. 3387 (2008)
152. Q Wang, C Li, Y Zou, H Wang, T Yi, C Huang Org. Biomol. Chem. 10 6740 (2012)
153. P Mahato, S Saha, E Suresh, R D Liddo, P P Parnigotto, M T Conconi, M K Kesharwani, B Ganguly, A Das Inorg. Chem. 51 1769 (2012)
154. Y Liu, X Lv, Y Zhao, M Chen, J Liu, P Wang, W Guo Dyes Pigm. 92 909 (2012)
155. Z Xu, J Yoon, D R Spring Chem. Commun. 46 2563 (2010)
156. P A Panchenko, Y V Fedorov, V P Perevalov, G Jonusauskas, O A Fedorova J. Phys. Chem. A 114 4118 (2010)
157. Q Zeng, Z Li, Y Dong, C Di, A Qin, Y Hong, L Ji, Z Zhu, C K W Jim, G Yu, Q Li, Z Li, Y Liu, J Qin, B Z Tang Chem. Commun. 70 (2007)
158. Y Dong, J W Y Lam, A Qin, Z Li, J Sun, H H-Y Sung, I D Williams, B Z Tang Chem. Commun. 40 (2007)
159. Y K Wu, X J Peng, J L Fan, S Gao, M Z Tian, J Z Zhao, S G Sun J. Org. Chem. 72 62 (2007)
160. Y Q Xu, Y Pang Chem. Commun. 46 4070 (2010)
161. H S Jung, K C Ko, J H Lee, S H Kim, S Bhuniya, J Y Lee, Y Kim, S J Kim, J S Kim Inorg. Chem. 49 8552 (2010)
162. M Suresh, A K Mandal, S Saha, E Suresh, A Mandoli, R D Liddo, P P Parnigotto, A Das Org. Lett. 12 5406 (2010)
163. X Cheng, H Jia, T Long, J Feng, J Qin, Z Li Chem. Commun. 47 11978 (2011)
164. J Wu, W Liu, J Ge, H Zhang, P Wang Chem. Soc. Rev. 40 3483 (2011)
165. P Wang, J Liu, X Lv, Y Liu, Y Zhao, W Guo Org. Lett. 14 520 (2012)
166. N Singh, N Kaur, B McCaughan, J F Callan Tetrahedron Lett. 51 3385 (2010)
167. US P. 5952491 (1999)
168. US P. 6124135 (2000)
169. GB P. 2306496 (1997)
170. US P. 5308773 (1994)
171. US P. 5472878 (1995)
172. US P. 8097725 (2012)