Fluorescent turn-on detection and assay of water based on 4-(2-dimethylaminoethyloxy)-N-octadecyl-1,8-naphthalimide with aggregation-induced emission enhancement

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

Volumn 97, Issue , 2012, Pages 352-358

  Sun, Yang ^a   Liang, Xuhua ^b   Wei, Song ^b   Fan, Jun ^b   Yang, Xiaohui ^a  

^a XI'AN UNIVERSITY OF ARTS AND SCIENCE   (China)

^b NORTHWEST UNIVERSITY   (China)

Author keywords

Aggregation induced emission enhancement (AIEE); Density functional theory (DFT); N Octadecyl 18 naphthalimide; Solvent effect; Twisted intramolecular charge transfer (TICT); Water probe

Indexed keywords

AGGREGATION-INDUCED EMISSIONS; DENSITY FUNCTIONAL THEORIES (DFT); N-OCTADECYL-18-NAPHTHALIMIDE; SOLVENT EFFECTS; TWISTED INTRA-MOLECULAR CHARGE TRANSFERS;

ACETONE; ACETONITRILE; CHARGE TRANSFER; EMISSION SPECTROSCOPY; ETHANOL; FLUORESCENCE; ORGANIC SOLVENTS; QUANTUM YIELD; SOLVENTS; SPECTRUM ANALYSIS;

DENSITY FUNCTIONAL THEORY;

4 (2 DIMETHYLAMINOETHYLOXY) N OCTADECYL 1,8 NAPHTHALIMIDE; 4-(2-DIMETHYLAMINOETHYLOXY)-N-OCTADECYL-1,8-NAPHTHALIMIDE; NAPHTHALIMIDE DERIVATIVE; PROTON; SOLVENT; WATER;

ABSORPTION; ARTICLE; CHEMISTRY; FLUORESCENCE; LIMIT OF DETECTION; PH; SPECTROFLUOROMETRY; STATIC ELECTRICITY;

ABSORPTION; FLUORESCENCE; HYDROGEN-ION CONCENTRATION; LIMIT OF DETECTION; NAPHTHALIMIDES; PROTONS; SOLVENTS; SPECTROMETRY, FLUORESCENCE; STATIC ELECTRICITY; WATER;

EID: 84865285766     PISSN: 13861425     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.saa.2012.06.017     Document Type: Article

References (40)

1. K.A. Fisher A new method for the analytical determination of the water content of liquids and solids Angew. Chem. 48 1935 394 396
2. R. Oguchi, K. Yamaguchi, and T. Shibamoto Determination of water content in common organic solvents by a gas chromatograph equipped with a megabore fused-silica column and a thermal conductivity detector J. Chromatogr. Sci. 11 1988 588 590
3. G.C. Miceli, Y.S. Chen, E.M. Girotto, Y. Li, A.W. Rinaldi, M.J. Yang, and A. Zanelli Prompt responsive sensors for water detection in organic solvents Sens. Actuators, B 2 2006 577 582
4. M.S. Gong, M.H. Lee, and H.W. Rhee Humidity sensor using cross-linked copolymers containing viologen moiety Sens. Actuators, B 73 2001 185 191
5. M. Matsuguchi, S. Umeda, Y. Sadaoka, and Y. Sakai Characterization of polymers for a capacitive-type humidity sensor based on water sorption behavior Sens. Actuators, B 49 1998 179 185
6. G.C. Miceli, A. Zanelli, A.W. Rinaldi, E.M. Girotto, M.J. Yang, Y.S. Chen, and Y. Li A model of polyelectrolyte conductance in moist solvents as a basis of water sensors Langmuir 21 2005 9704 9708
7. Y.B. Shim, and J.H. Park Humidity sensor using chemically synthesized poly(1,5-diaminonaphthalene) doped with carbon J. Electrochem. Soc. 1 2000 381 385
8. S. Cho, H. Chung, Y.A. Woo, and H.J. Kim Determination of water content in ethanol by miniaturized near-infrared (NIR) system Bull. Korean Chem. Soc. 1 2005 115 117
9. Y. Ooyama, M. Sumomogi, T. Nagano, K. Kushimoto, K. Komaguchi, I. Imae, and Y. Harima Detection of water in organic solvents by photo-induced electron transfer method Org. Biomol. Chem. 9 2011 1314 1316
10. Y. Ooyama, A. Matsugasako, K. Oka, T. Nagano, M. Sumomogi, K. Komaguchi, I. Imae, and Y. Harima Fluorescence PET (photo-induced electron transfer) sensors for water based on anthracene-boronic acid ester Chem. Commun. 47 2011 4448 4450
11. Y. Ooyama, H. Egawa, and K. Yoshida The design of a novel fluorescent PET sensor for proton and water: a phenylaminonaphtho[1,2-d]oxazol-2-yl-type fluorophore containing proton donor and acceptor groups Dyes Pigm. 82 2009 58 64
12. Z.W. Li, Q.W. Yang, R.X. Chang, G.C. Ma, M.X. Chen, and W.Q. Zhang N-Heteroaryl-1,8-naphthalimide fluorescent sensor for water: molecular design, synthesis and properties Dyes Pigm. 88 2011 307 314
13. C.G. Niu, L.M. Li, P.Z. Qin, G.M. Zeng, and Y. Zhang Determination of water content in organic solvents by naphthalimide derivative fluorescent probe Anal. Sci. 6 2010 671 674
14. Z.Z. Li, C.G. Niu, G.M. Zeng, and P.Z. Qin Fluorescence sensor for water content in organic solvents based on covalent immobilization of benzothioxanthene Chem. Lett. 7 2009 698 699
15. M.G. Choi, H.H. Joo, Y.H. Kim, S. Ahn, and S.K. Chang Ratiometric determination of water content in acetonitrile by a fluorescein derivative bearing two pyrene subunits Bull. Korean Chem. Soc. 31 2010 2995 2998
16. S.Y. Cha, M.G. Choi, H.R. Jeon, and S.K. Chang Negative solvatochromism of merocyanine dyes: application as water content probes for organic solvents Sens. Actuators, B 157 2011 14 18
17. J.S. Kim, M.G. Choi, Y. Huh, M.H. Kim, S.H. Kim, S.Y. Wang, and S.K. Chang Determination of water content in aprotic organic solvents using 8-hydroxyquinoline based fluorescent probe Bull. Korean Chem. Soc. 12 2006 2058 2060
18. K.N. Kim, K.C. Song, J.H. Noh, and S.K. Chang A simple phenol-indole dye as a chromogenic probe for the ratiometric determination of water content in organic solvents Bull. Korean Chem. Soc. 1 2009 197 200
19. J. Luo, J.W.Y. Lam, L. Cheng, H. Chen, C. Qiu, H.S. Kwok, X. Zhan, Y. Liu, D. Zhu, and B.Z. Tang Aggregation-induced emission of 1-methyl-1,2,3,4, 5-pentaphenylsilole Chem. Commun. 18 2001 1740 1741
20. J. Chen, C.C.W. Law, J.W.Y. Lam, Y.P. Dong, S.M.F. Lo, I.D. Williams, D. Zhu, and B.Z. Tang Synthesis, light emission, nanoaggregation, and restricted intramolecular rotation of 1, 1-substituted 2,3,4,5-tetraphenylsiloles Chem. Mater. 15 2003 1535 1546
21. Y. Hong, J.W.Y. Lam, and B.Z. Tang Aggregation-induced emission: phenomenon, mechanism and applications Chem. Commun. 29 2009 4332 4353
22. J. Liu, J.W.Y. Lam, and B.Z. Tang Aggregation-induced emission of silole molecules and polymers: fundamental and applications J. Inorg. Organomet. Polym Mater. 19 2009 249 285
23. S. Zhang, A.J. Qin, J.Z. Sun, and B.Z. Tang Mechanism study of aggregation-induced emission Proc. Chem. 4 2011 623 636
24. Y. Sun, S. Wei, Y.Y. Zhao, X.Y. Hu, and J. Fan Interactions between4-(2-dimethylaminoethyloxy)-N-octadecyl-1,8-naphthalimide and serum albumins: investigation by spectroscopic approach J. Lumin. 132 2012 879 886
25. ADF 2009.01, SCM, Theoretical Chemistry, Vrije Universiteit, Amsterdam, The Netherlands. Available at: < http://www.scm.com >
26. A.C. Neto, E.P. Muniz, R. Centoducatte, and F.E. Jorge Gaussian basis sets for correlated wave functions. Hydrogen, helium, first-and second-row atoms J. Mol. Struct. 718 2005 219 224
27. G.G. Camiletti, S.F. Machado, and F.E. Jorge Gaussian basis set of double zeta quality for atoms K through Kr: Application in DFT calculations of molecular properties J. Comput. Chem. 29 2008 2434 2444
28. E. Von Lippert Spektroskopische bestimmung des dipolomomentes aromatischer verbindungen im ersten angeregten singluettzustand Z. Electrochem. 61 1957 962 975
29. H.W. Dirr Solvent effects on the spectroscopic properties of aflatoxin B1 11 1987 1137 1140
30. A. Hawe, M. Sutter, and W. Jiskoot Extrinsic fluorescent dyes as tools for protein characterization Pharm. Res. 25 2008 1487 1499
31. B. Valeur Molecular Fluorescence Principles Applications 2002 Wiley-VCH Weinheim Germany Chapter 3
32. E. Lippert, W. Rettig, V.B. Koutecky, F. Heisel, and J.A. Miehe Photophysics of internal twisting Adv. Chem. Phys. 68 1987 1 173
33. Z.R. Grabowski, and K. Rotkiewicz Structural changes accompanying intramolecular electron transfer: focus on twisted intramolecular charge-transfer states and structures Chem. Rev. 103 2003 3899 4031
34. N.I. Georgiev, V.B. Bojinov, and P.S. Nikolov The design, synthesis and photophysical properties of two novel 1, 8-naphthalimide fluorescent pH sensors based on PET and ICT Dyes Pigm. 88 2011 350 357
35. J.M. Chovelon, and I. Grabchev A novel fluorescent sensor for metal cations and protons based of bis-1, 8-naphthalimide Spectrochim. Acta A 67 2007 87 91
36. Q.Q. Li, S.S. Yu, Z. Li, and J.G. Qin New indole-containing luminophores: convenient synthesis and aggregation-induced emission enhancement J. Phys. Org. Chem. 22 2009 241 246
37. Y.N. Hong, X. Hao, J.W.Y. Lam, M. Häußler, J.Z. Liu, Y. Yu, Y.C. Zhong, H.H.Y. Sung, I.D. Williams, K.S. Wong, and B.Z. Tang Fluorescent bioprobes: structural matching in the docking processes of aggregation-induced emission fluorogens on dna surfaces Chem. Commun. 4 2010 1232 1245
38. X.Q. Zhang, Z.G. Chi, B.J. Xu, H.Y. Li, Z.Y. Yang, X.F. Li, S.W. Liu, Y. Zhang, and J.R. Xu Synthesis and characterization of triphenylethylene derivatives with aggregation-induced emission characteristics J. Fluoresc. 5 2011 1969 1977
39. H. Yao, Y. Morita, and K. Kimura Effect of organic solvents on J aggregation of pseudoisocyanine dye at mica/water interfaces: Morphological transition from three-dimension to two-dimension J. Colloid Interface Sci. 318 2008 116 123
40. R.R. Hu, E. Lager, A.A. Aguilar, J.Z. Liu, J.W.Y. Lam, H.H.Y. Sung, I.D. Williams, Y.C. Zhong, K.S. Wong, E.P. Cabrera, and B.Z. Tang Twisted intramolecular charge transfer and aggregation-induced emission of bodipy derivatives J. Phys. Chem. C 113 2009 15845 15853