On the signalling pathways and CuII-mediated anion indication of N-meso-substituted heptamethine cyanine dyes

Chemistry - A European Journal

Volumn 15, Issue 13, 2009, Pages 3173-3185

  Descalzo, Ana B ^a   Rurack, Knut ^a  

^a BAM FEDERAL INSTITUTE FOR MATERIALS RESEARCH AND TESTING   (Germany)

Author keywords

Anions; Copper; Crown compounds; Dyes pigments; Polymethines

Indexed keywords

ABSORPTION; AMINES; CHROMOPHORES; COORDINATION REACTIONS; COPPER; METAL IONS; PROTONATION; SPECTROSCOPIC ANALYSIS; TRACE ANALYSIS;

AMINO GROUPS; ANIONS; AQUEOUS SOLUTIONS; AT WAVELENGTHS; BATHOCHROMIC SHIFTS; BLUE-SHIFTS; COPPER IONS; CROWN COMPOUNDS; CYANINE DYES; DISPLACEMENT ASSAYS; DYES/PIGMENTS; GROUND-STATE; MESO POSITIONS; NEAR INFRA REDS; POLYMETHINE; POLYMETHINE DYES; POLYMETHINES; REALISTIC CONDITIONS; SIGNALLING PATHWAYS; SPECTROSCOPIC RESPONSE; SPECTROSCOPIC STUDIES; STOKES SHIFTS;

NEGATIVE IONS;

EID: 63749099870     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802087     Document Type: Article

References (148)

1. A. Gómez-Hens, M. P. Aguilar-Caballos, TrAC Trends Anal. Chem. 2004, 24, 127-136;
2. S. Achilefu, Technol. Cancer Res. Treat. 2004, 3, 393-409;
3. G. Palonay, J. Salon, J. Sowell, L. Strekowski, Molecules 2004, 9, 40-49;
4. N. Johnsson, K. Johnsson, ACS Chem. Biol. 2007, 2, 31-38;
5. K. Kiyose, H. Kojima, T. Nagano, Chem. Asian J. 2008, 3, 506-515;
6. A. B. Descalzo, H.-J. Xu, Z. Shen, K. Rurack, Ann. N. Y. Acad. Sci. 2008, 1130, 164-171;
7. C. L. Amiot, S. Xu, S. Liang, L. Pan, J. X. Zhao, Sensors 2008, 8, 3082-3105.
8. S. McWhorter, S. A. Soper, Electrophoresis 2000, 21, 1267-1280;
9. M. Fricker, J. Runions, Annu. Rev. Plant Biol. 2006, 57, 79-107;
10. J. H. Rao, A. Dragulescu-Andrasi, H. Q. Yao. Curr. Opin. Biotechnol. 2007, 18, 17-25.
11. Near-Infrared Applications in Biotechnology (Ed.: R. Raghavachari), Marcel Dekker, New York, 2001.
12. W. Siebrand, J. Chem. Phys. 1967, 46, 440-447.
13. Y.-H. Yu, A. B. Descalzo, Z. Shen, H. Röhr, Q. Liu, Y.-W. Wang, M. Spieles, Y.-Z. Li, K. Rurack, X.-Z. You, Chem. Asian J. 2006, 1, 176-187.
14. G. M. Fischer, A. P. Ehlers, A. Zumbusch, E. Daltrozzo, Angew. Chem. 2007, 119, 3824-3827:
15. Angew. Chem. Int. Ed. 2007, 46, 3750-3753;
16. J.R. Johnson, N. Fu, E. Arunkumar, W. M. Leevy, S. T. Gammon. D. Piwnica-Worms, B. D. Smith, Angew. Chem. 2007, 119, 5624-5627:
17. Angew. Chem. Int. Ed. 2007, 46, 5528-5531;
18. A. Harriman, L. J. Mallon, S. Goeb, R. Ziessel, Phys. Chem. Chem. Phys. 2007, 9, 5199-5201;
19. K. Umezawa, Y. Nakamura, H. Makino, D. Citterio, K. Suzuki, J. Am. Chem. Soc. 2008, 130, 1550-1551;
20. J. Killoran, S. O. McDonnell, J. F. Gallagher, D. F. O'Shea, New J. Chem. 2008, 32, 483-489;
21. X. Song, D. S. Kassaye, J. W. Foley, J. Fluoresc. 2008, 18, 513-518;
22. Y. Yang, M. Lowry, X. Xu, J. O. Escobedo, M. Sibrian-Vazcluez, L. Wong, C. M. Schowalter, T. J. Jensen, F. R. Fronczek, I. M. Warner, R. M. Strongin, Proc. Natl. Acad. Sci. USA 2008, 105, 8829-8834;
23. M. H. V. Werts, R. H. Woudenberg, P. G. Emmerink, R. van Gassel, J. W. Hofstraat, J. W. Verhoeven. Angew. Chem. 2000, 112, 4716-4718;
24. Angew. Chem. Int. Ed. 2000, 39, 4542-4544.
25. J. Fabian, H. Nakazumi, M. Matsuoka, Chem. Rev. 1992, 92, 1197-1226.
26. R. A. Yotter, L. A. Lee, D. M. Wilson. IEEE Sens. J. 2004. 4, 395-411:
27. this interest was also fuelled by the growing popularity of long-wavelength absorbing melal nanoparlicles in (bio)chemical analysis, see, for example, M. C. Daniel, D. Astruc, Chem. Rev. 2004, 104, 293-346.
28. A.-J. Tong, A. Yamauchi, T. Hayashita, Z.-Y. Zhang, B. D. Smith, N. Teramae. Anal. Chem. 2001, 73, 1530-1536;
29. H. Tong, Y. Hong, Y. Dong, M. Haussler, J. W. Y. Lam, Z. Li, Z. Guo, Z. Guo, B. Z. Tang, Chem. Commun. 2006, 3705-3707;
30. H. Tong, Y. Hong, Y. Dong, M. Haussler, Z. Li, J. W. Y. Lam, Y. Dong, H. H.-Y. Sung, I. D. Williams, B. Z. Tang, J. Phys. Chem. B 2007, 111, 11817-11823.
31. I. Murkovic, O.S. Wolfbeis, Sens. Actuators B 1997, 39, 246-251;
32. D. Y. Sasaki, D. R. Shnek. D. W. Pack, F. H. Arnold, Angew. Chem. 1995, 107, 994-996;
33. Angew. Chem. Int. Ed. Engl. 1995, 34, 905-907;
34. M. Berton, F. Mancin, G. Stocchero, P. Tecilla, U. Tonellato, Langmuir 2001, 17, 7521-7528;
35. J. L. Pincus, C. Jin, W. Huang, H. K. Jacobs, A. S. Gopalan, Y. Song, J. A. Shelnutt, D. Y. Sasaki, J. Mater. Chem. 2005, 15, 2938-2945;
36. Y. Che, X. Yang, L. Zang, Chem. Commun. 2008, 1413-1415.
37. V. Král, F. P. Schmidtchen, K. Lang, M. Berger, Org. Lett. 2002, 4, 51-54;
38. K. Sato, Y. Sadamitsu, S. Arai, T. Shimada, H. Inoue, T. Yamagishi, Heterocycles 2005, 66, 119-127.
39. Y. Dong, J. W. Y. Lam; A. Qin, Z. Li, J. Liu, J. Sun, Y. Dong, B. Z. Tang, Chem. Phys. Lett. 2007, 446, 124-127;
40. A. Qin, Z. Li, J. Liu, J. Sun, Y. Dong, B. Z. Tang, Chem. Phys. Lett. 2007, 446, 124-127;
41. A. Qin, Z. Li, J. Liu, J. Sun, Y. Dong, B. Z. Tang, Chem. Phys. Lett. 2007, 446, 124-127.
42. S.-J. Chen, H.-T. Chang, Anal. Chem. 2004, 76, 3727-3734;
43. Y. Kubo, S. Uchida, Y. Kemmochi, T. Okubo, Tetrahedron Lett. 2005, 46, 4369-4372;
44. J. Liu, Y. Lu, J. Am. Chem. Soc. 2005, 127, 12677-12683;
45. S. Y. Lin, S.H. Wu, C.H. Chen, Angew. Chem. 2006, 118, 5070-5073 ;
46. Angew. Chem. Int. Ed. 2006, 45, 4948-4951;
47. K. Konishi, T. Hiratani, Angew. Chem. 2006, 118, 5315-5318;
48. Angew. Chem. Int. Ed. 2006, 45, 5191-5194;
49. W. Zhao, W. Chiuman, M. A. Brook, Y. Li, ChemBioChem 2007, 8, 727-731;
50. A.C. Lee. J.-S. Ye, S.N. Tan. D. P. Poenar, F.-S. Sheu, C. K. Heng, T. M. Lim, Nanotechnology 2007, 18, 455102;
51. C.-C. Huang, H.-T. Chang, Chem. Commun. 2007, 1215-1217.
52. M. A. Balbo Block, S. Hecht, Macromolecules 2004, 37, 4761-4769;
53. H. Sun, F. Feng, M. Yu, S. Wang, Macromol. Rapid Commun. 2007, 28, 1905-1911;
54. B. R. Crenshaw, J. Kunzelman, C. E. Sing, C. Ander, C. Weder, Macromol. Chem. Phys. 2007, 208, 572-580;
55. J. Kunzelman, B. R. Crenshaw, C. Weder, J. Mater. Chem. 2007, 17, 2989-2991;
56. H. Li, S. Valiyaveettil, Macromolecules 2007, 40, 6057-6066;
57. A. Satrijo, T. M. Swager, J. Am. Chem. Soc. 2007, 129,16020-16028.
58. H. Murakami, T. Nagasaki, I. Hamachi, S. Shinkai, J. Chem. Soc. Perkin Trans. 2 1994, 975-981;
59. A. Ajayaghosh, E. Arunkumar, J. Daub. Angew. Chem. 2002, 114, 1844-1847;
60. Angew. Chem. Int. Ed. 2002, 41, 1766-1769;
61. J. V. Ros-Lis, R. Martínez-Máñez, K. Rurack, F. Sancenón, J. Soto, M. Spieles, Inorg. Chem. 2004, 43, 5183-5185;
62. R. Jelinek, S. Kolusheva, Top. Curr. Chem. 2007, 277, 155-180.
63. C.-Q. Zhu, Y.-Q. Wu, H. Zheng, J.-L. Chen, D.-H. Li, S.-H. Li, J.-G. Xu, Anal. Sci. 2004, 20, 945-949;
64. B. A. Armitage. Top. Curr. Chem. 2005, 253, 55-76;
65. T. D. Slavnova, H. Görner, A. K. Chibisov, J. Phys. Chem. B 2007, 111, 10023-10031;
66. G. Y. Guralchuk, A. V. Sorokin, I. K. Katrunov, S. L. Yefimova, A. N. Lebedenko, Y. V. Malyukin, S. M. Yarmoluk, J. Fluoresc. 2007, 17, 370-376.
67. A. D. Kachkovski, N. M. Kovalenko, Dyes Pigm. 1997, 35, 131-148.
68. N. Tyulyulkov, J. Fabian, A. Mehlhorn, F. Dietz, A. Tadjer. Polymethine Dyes, St. Kliment Ohridski University Press, Sofia, 1991.
69. X. Peng, F. Song, E. Lu, Y. Wang, W. Zhou, J. Fan, Y. Gao. J. Am. Chem. Soc. 2005, 127, 4170-4171.
70. M. Zhu, M. Yuan, X. Liu, J. Xu, J. Lv, C. Huang, H. Liu, Y. Li, S. Wang, D. Zhu. Org. Lett. 2008, 10, 1481-1484.
71. K. Kiyose, H. Kojima, Y. Urano, T. Nagano, J Am. Chem. Soc. 2006, 128, 6548-6549;
72. B. Tang, H. Huang, K. Xu, L. Tong, G. Yang, X. Liu, L. An. Chem. Commun. 2006, 3609-3611;
73. W. Pham, L. Cassell. A. Gillman, D. Koktysh, J. C. Gore, Chem. Commun. 2008, 1895-1897.
74. L.-C. Zhou, G.-J. Zhao, J.-F. Liu, K.-L. Han. Y.-K. Wu, X.-J. Peng, M.-T. Sun. J. Photochem. Photobiol. A 2007. 187, 305-310;
75. Y. Xu, Y. Liu, X. Qian, J. Photochem. Photobiol. A 2007, 190, 1-8;
76. L.-C. Zhou, J.-Y. Liu, G.-J. Zhao, Y. Shi, X.-J. Peng, K.-L. Han. Chem. Phys 2007. 333, 179-185;
77. B. Tang, L. J Cui, K. H. Xu, L. L. Tong, G. W. Yang, L. G. An. ChemBioChem 2008, 9, 1159-1164.
78. Z. Zhang, M. Y. Berezin, J. L. F. Kao, A. d'Avignon, M. Bai, S. Achilefu. Angew. Chem. 2008, 120, 3640-3643:
79. Angew. Chem. Int. Ed. 2008,47, 3584-3587.
80. K. Inoue, L. Zhuang, D. M. Maddox, S. B. Smith, V. Ganapathy, J. Biol. Chem. 2002, 277, 39469-39476;
81. C. Demigne, H. Sabboh, C. Puel, C. Remesy, V. Coxam, Nutr. Res. Rev. 2004, 17, 249-258;
82. M. Marangella, M. Di Stefano, S. Casalis, S. Berutti, P. D'Amelio, G. C. Isaia. Calcif. Tissue Int. 2004, 74, 330-335.
83. G. R. Stoppa, M. Cesquini, E. A. Roman, P. Prada, A. S. Torsoni, T. Romanatto, M. J. Saad, L. A. Velloso, M. A. Torsoni, J. Endocrinol. 2008, 198, 157-168.
84. P. R. Ryan, E. Delhaize, D. L. Jones. Annu. Rev. Plant Physiol. 2001, 52, 527-560;
85. P. Hinsinger, Plant Soil 2001. 237, 173-195.
86. F. R. Jensen, C. H. Bushweller, J. Am. Chem. Soc. 1969, 91, 5774-5782.
87. K. Rurack, M. L. Dekhtyar, J. L. Bricks, U. Resch-Genger, W. Rettig, J. Phys. Chem. A 1999, 103, 9626-9635.
88. J. Q. Umberger, Photogr. Sci Eng. 1967, 11, 392-399.
89. J. B. Birks, Photophysics of Aromatic Molecules, Wiley-Interscience, New York, 1970.
90. W. West, S. Pearce, F. Grum, J. Phys. Chem. 1967, 71, 1316-1326;
91. P. M. Henrichs, S. Gross, J. Am. Chem. Soc. 1976, 98, 7169-7175;
92. R. Allmann, H.-J. Anis, R. Benn, W. Grahn, S. Olejnek, A. Waskowska, Angew. Chem. 1983, 95, 900-901:
93. Angew. Chem. Int. Ed. Engl. 1983, 22, 876-877;
94. N. Vranken, S. Jordens, G. De Beider, M. Lor, E. Rousseau G. Schweitzer, S. Toppel, M. van der Auweraer, F. C. De Schryver, J. Phys. Chem. A 2001, 105, 10196-10203.
95. N. Serpone, M. R. V. Sahyun, J. Phys. Chem. 1994, 98, 734-737;
96. D. Noukakis, M. van der Auweraer, S. Toppet, F. C. De Schryver, J. Phys. Chem. 1995, 99, 11860-11866;
97. G. Ponterini, M. Fiorini, D. Vanossi, A. S. Tatikolov, F. Momicchioli, J. Phys. Chem. A 2006, 110, 7527-7538.
98. V. Khimenko, A. K. Chibisov, H. Görner, J. Phys. Chem. A 1997, 101, 7304-7310.
99. S. A. Soper, Q. L. Mattingly, J. Am. Chem. Soc. 1994, 116, 3744-3752;
100. O. Mader, K. Reiner, H.-J. Egelhaaf, R. Fischer, R. Brock, Bioconjugate Chem. 2004, 15, 70-78.
101. -1) and is not discussed further here.
102. -1.
103. H. Kuhn, Angew. Chem. 1959, 71, 93-101.
104. W. Grahn, W. Mrosek, C. Reichardt, Chem. Ber. 1977, 110, 1674-1683.
105. Y. L. Slominskii, I. D. Radchenko, A. I. Tolmachev, Zh. Org. Khim. 1979, 15, 400-407.
106. W. Rettig, K. Rurack, M. Sczepan in New Trends in Fluorescence Spectroscopy (Eds.: B. Valeur, J.-C, Brochon), Springer, Berlin, 2001, pp. 125-155;
107. Z. R. Grabowski, K. Rotkiewicz, W. Rettig. Chem. Rev. 2003, 103, 3899-4031.
108. J. T. Knudlson, E. M. Eyring, J. Phys. Chem. 1974, 78, 2355-2363.
109. It is also known that the pholochemistry of cyanine dyes can depend on the nature of the counterion. However, it has been shown in several studies that this influence is negligible in highly polar solvents such as acetonitrile or alcohols because the tendency for ion-pair formation is too low. See, for example: A. S. Tatikolov, L. A. Shvedova, N. A. Derevyanko, A. A. Ishchenko, V. A. Kuz'min, Chem. Phys. Lett. 1992, 190, 291-297;
110. A. S. Tatikolov, K. S. Dzhulibekov, L. A. Shvedova, V. A. Kuzmin, A. A. Ishchenko, J. Phys. Chem. 1995, 99, 6525-6529.
111. R. D. Hancock, R. J. Motekaitis. J. Mashishi, I. Cukrowski, J. H. Reibenspies, A. E. Martell. J. Chem. Soc. Perkin Trans. 2 1996, 1925-1929.
112. L. S. Choi, G. E. Collins, Chem. Commun. 1998, 893-894.
113. G. E. Collins, L. S. Choi, J. H. Callahan, J. Am. Chem. Soc 1998, 120, 1474-1478.
114. The corresponding fluorescence is found at λ = 797 nm.
115. Although we doubt the involvement of ICT processes put forward by Zhu et al., see discussion in previous paragraphs.
116. A. B. Descalzo, R. Martinez-Manez, R. Radeglia, K. Rurack, J. Soto, J. Am. Chem. Soc. 2003, 125, 3418-3419.
117. M. Boiocchi, L. Fabbrizzi, M. Licchelli, D. Sacchi, M. Vazquez, C. Zampa, Chem. Commun. 2003, 1812-1813;
118. S. H. Kim, J. S. Kim, S. M. Park, S.-K. Chang, Org. Lett. 2006, 8, 371-374.
119. Y. L. Slominskii, S. V. Popov, I. V. Repyakh, M. I. Povolotskii, A. D. Kachkovskii, G. G. Dyadyusha, Teor. Eksp. Khim. 1987, 23, 687-692.
120. N. S. Spasokukotskii, A. F. Vompe, I. I. Levkoev, N. N. Sveshnikov, Zh. Org. Khim. 1980, 16, 2427-2434.
121. This trend in protonation susceptibility is even found and has been experimentally verified for unsubstituted symmetric cyanines. See. for example: A. I. Tolmachev, M. Y. Komilov, E. F. Karaban, Teor. Eksp. Khim. 1976, 12, 817-821.
122. L. G. S. Brooker, R. H. Sprague, C. P. Smyth, G. L. Lewis, J. Am. Chem. Soc. 1940, 62, 1116-1125;
123. L. H. Feldman, A. H. Herz, T. H. Regan, J. Phys. Chem. 1968, 72, 2008-2013.
124. M. Niaz Khan, J.-P. Fleury, P. Baumlin, C. Hubschwerlen. Tetrahedron 1985, 41, 5341-5345. Note that 13 formally represents a tetramethine chromophore. Accordingly, the main chromophore, that is. the polymethine chain in 14 can be seen as a bridged analogue of 13.
125. 4) shows an isosbeslic point. the backward titration with base (NaOH) does not lead to the reappearance of the original trace, but to different, hypsochromically shifted spectra for all the cases labelled "ir" in Table 2 (e.g., see Figure S6 in the Supporting Information). On the other hand, the spectral shape is unchanged if base is added to a neutral solution of the dyes (e.g.. see Figure S6). Apparently, once protonated. the product formed is susceptible to secondary' reactions. Note that Peng et al. (ref. [19]) did not report on the reversibility of their pH titration experiments.
126. 0 transition in 12 and 13 is an exclusive HOMO-LUMO transition, the transition in 14 is a fourfold mixed one with reduced oscillator strength and only approximately 2/3 HOMO-LUMO contribution.
127. V. J. Thom, G. D. Hosken, R. D. Hancock, Inorg. Chem. 1985, 24, 3378-3381.
128. A. Bianchi, M. Micheloni, P. Paoletti, Coord. Chem. Rev. 1991, 110, 17-113.
129. K. A. Connors, Binding Constants. Wiley, New York, 1987.
130. J. N. Weiss, FASEB J. 1997, 11, 835-841.
131. J. Raker, T. E. Glass, J. Org. Chem. 2002, 67, 6113-6116.
132. II and 1 nor to a formation constant of dimers, trimers or higher oligomeric aggregates, but is only a useful measure for the overall sensory process. A more detailed investigation of the aggregation process is currently being performed in our laboratory.
133. I salts of the anions employed do not lead to aggregate formation. Furthermore, as would be expected, aggregate formation is significantly hampered or can be reversed with an excess of neat cyclam or ethylenediaminetetraacetic acid (EDTA). See Figure S8 in the Supporting Information for an exemplary back-titration with EDTA.
134. K. Rurack. Spectrochim. Acta, Part A 2001, 57, 2161-2195.
135. Note that the binding constant for the copper citrate complex in water at room temperature is log K = 9.3, see: T. D. Field, J. L. McCourt, W. A. E. McBryde, Can. J. Chem. 1974, 52, 3119-3124.
136. D. R. Spears, J. B. Vincent. Biotechnol. Bioeng. 1997, 53, 01-09.
137. B. García-Acosta, R. Martínez-Máñez, F. Sancenón, J. Soto, K. Rurack, M. Spieles, E. García-Breijo, L. Gil, Inorg. Chem. 2007, 46, 3123-3135.
138. K. J. Wallace, B. T. Nguyen, E. V. Anslyn in Encycl. Supramol. Chem. 2006, DOI: 10.1081/E-ESMC-120041517;
139. A. Buryak, K. Severin, J. Am. Chem. Soc. 2005, 127, 3700-3701.
140. C. Spitz, S. Dähne, A. Ouart, H. W. Abraham, J. Phys. Chem. B 2000, 104, 8664-8669;
141. S. Kirstein, H. von Berlepsch, C. Böttcher, C. Burger, A. Ouart, G. Reck, S. Dähne, ChemPhysChem 2000, 1, 146-150.
142. U. Resch, K. Rurack, Proc. SPIE-Int. Soc. Opt. Eng. 1997, 3105, 96-103.
143. Z. Shen, H. Röhr, K. Rurack, H. Uno, M. Spieles, B. Schulz, G. Reck, N. Ono, Chem. Eur. J. 2004, 10. 4853-4871.
144. Global Unlimited, version 2.2. Laboratory for Fluorescence Dynamics. University of Illinois, IL.
145. A. D. Becke, J. Chem. Phys. 1993, 98. 5648-5652.
146. C. Ue, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
147. Gaussian 03. Revision D.01, M.J. Frisch, G.W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery. Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C, Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc.. Wallingford CT. 2004.
148. M. C. Zemer, G. H. Loew, R. F. Kirchner, U. T. Mueller-Westerhoff, J. Am. Chem. Soc. 1980, 102, 589-599.