Rational design of a chromo- and fluorogenic hybrid chemosensor material for the detection of long-chain carboxylates

Journal of the American Chemical Society

Volumn 127, Issue 1, 2005, Pages 184-200

  Descalzo, Ana B ^a   Rurack, Knut ^b   Weisshoff, Hardy ^b,d   Martínez Máñez, Ramón ^a   Marcos, M Dolores ^a   Amorós, Pedro ^c   Hoffmann, Katrin ^b   Soto, Juan ^a  

^a UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

^b Div 13   (Germany)

^c UNIVERSITY OF VALENCIA   (Spain)

^d HUMBOLDT UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION; BIOCHEMISTRY; CARBOXYLATION; FLUORESCENCE; HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

HYBRID CHEMOSENSOR MATERIALS; LONG-CHAIN CARBOXYLATES; MOIETY; MOLECULAR SENSORS;

OPTICAL SENSORS;

FATTY ACID; FLUORESCENT DYE; M1ME; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; DRUG DESIGN; FATTY ACID ANALYSIS; HYDROGEN BOND; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL BIOSENSOR; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANIONS; COLORING AGENTS; FATTY ACIDS, NONESTERIFIED; FLUORESCENT DYES; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OPTICS; SPECTROMETRY, FLUORESCENCE; WATER;

EID: 12144278299     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045683n     Document Type: Article

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91. Comprehensive and up to date information on the most common and commercially available fluorescent stains and labels in combination with the respective instrumentation is given on the CD-ROM series The Purdue Cytometry CD-ROM; Robinson, J. P., Purdue University Cytometry Laboratories: West Lafayette, 1996-2003; Vol. 1-7 and Purdue Microscopy, Image Analysis and 3D Reconstruction CD-ROM series; Pawley, J. B., Robinson, J. P., Eds.; Purdue University: West Lafayette, 1998; Vol. 1 or on the web site of the PUCL at http://www.cyto.purdue.edu.
92. Comprehensive and up to date information on the most common and commercially available fluorescent stains and labels in combination with the respective instrumentation is given on the CD-ROM series The Purdue Cytometry CD-ROM; Robinson, J. P., Purdue University Cytometry Laboratories: West Lafayette, 1996-2003; Vol. 1-7 and Purdue Microscopy, Image Analysis and 3D Reconstruction CD-ROM series; Pawley, J. B., Robinson, J. P., Eds.; Purdue University: West Lafayette, 1998; Vol. 1 or on the web site of the PUCL at http://www.cyto.purdue.edu.
93. Easily reducible PAH fluorophores are employed in most photoinduced electron transfer (PET) type probes for anions, many of them showing fluorescence quenching upon binding to the electron rich analytes; see e.g. (a) Nishizawa, S.; Kaneda, H.; Uchida, T.; Teramae, N. J. Chem. Soc., Perkin Trans. 2 1998, 2325-2327. (b) Kubo, Y.; Tsukahara, M.; Ishihara, S.; Tokita, S. Chem. Commun. 2000, 653-654. (c) Gunnlaugsson, T.; Davis, A. P.; Glynn, M. Chem. Commun. 2001, 2556-2557. (d) Sasaki, S.; Citterio, D.; Ozawa, S.; Suzuki, K. J. Chem. Soc., Perkin Trans. 2 2001, 2309-2313. (e) Nishizawa, S.; Cui, Y.-Y.; Minagawa, M.; Morita, K.; Kato, Y.; Taniguchi, S.; Kato, R.; Teramae, N. J. Chem. Soc., Perkin Trans. 2 2002, 866-870.
94. Easily reducible PAH fluorophores are employed in most photoinduced electron transfer (PET) type probes for anions, many of them showing fluorescence quenching upon binding to the electron rich analytes; see e.g. (a) Nishizawa, S.; Kaneda, H.; Uchida, T.; Teramae, N. J. Chem. Soc., Perkin Trans. 2 1998, 2325-2327. (b) Kubo, Y.; Tsukahara, M.; Ishihara, S.; Tokita, S. Chem. Commun. 2000, 653-654. (c) Gunnlaugsson, T.; Davis, A. P.; Glynn, M. Chem. Commun. 2001, 2556-2557. (d) Sasaki, S.; Citterio, D.; Ozawa, S.; Suzuki, K. J. Chem. Soc., Perkin Trans. 2 2001, 2309-2313. (e) Nishizawa, S.; Cui, Y.-Y.; Minagawa, M.; Morita, K.; Kato, Y.; Taniguchi, S.; Kato, R.; Teramae, N. J. Chem. Soc., Perkin Trans. 2 2002, 866-870.
95. Easily reducible PAH fluorophores are employed in most photoinduced electron transfer (PET) type probes for anions, many of them showing fluorescence quenching upon binding to the electron rich analytes; see e.g. (a) Nishizawa, S.; Kaneda, H.; Uchida, T.; Teramae, N. J. Chem. Soc., Perkin Trans. 2 1998, 2325-2327. (b) Kubo, Y.; Tsukahara, M.; Ishihara, S.; Tokita, S. Chem. Commun. 2000, 653-654. (c) Gunnlaugsson, T.; Davis, A. P.; Glynn, M. Chem. Commun. 2001, 2556-2557. (d) Sasaki, S.; Citterio, D.; Ozawa, S.; Suzuki, K. J. Chem. Soc., Perkin Trans. 2 2001, 2309-2313. (e) Nishizawa, S.; Cui, Y.-Y.; Minagawa, M.; Morita, K.; Kato, Y.; Taniguchi, S.; Kato, R.; Teramae, N. J. Chem. Soc., Perkin Trans. 2 2002, 866-870.
96. Easily reducible PAH fluorophores are employed in most photoinduced electron transfer (PET) type probes for anions, many of them showing fluorescence quenching upon binding to the electron rich analytes; see e.g. (a) Nishizawa, S.; Kaneda, H.; Uchida, T.; Teramae, N. J. Chem. Soc., Perkin Trans. 2 1998, 2325-2327. (b) Kubo, Y.; Tsukahara, M.; Ishihara, S.; Tokita, S. Chem. Commun. 2000, 653-654. (c) Gunnlaugsson, T.; Davis, A. P.; Glynn, M. Chem. Commun. 2001, 2556-2557. (d) Sasaki, S.; Citterio, D.; Ozawa, S.; Suzuki, K. J. Chem. Soc., Perkin Trans. 2 2001, 2309-2313. (e) Nishizawa, S.; Cui, Y.-Y.; Minagawa, M.; Morita, K.; Kato, Y.; Taniguchi, S.; Kato, R.; Teramae, N. J. Chem. Soc., Perkin Trans. 2 2002, 866-870.
97. Easily reducible PAH fluorophores are employed in most photoinduced electron transfer (PET) type probes for anions, many of them showing fluorescence quenching upon binding to the electron rich analytes; see e.g. (a) Nishizawa, S.; Kaneda, H.; Uchida, T.; Teramae, N. J. Chem. Soc., Perkin Trans. 2 1998, 2325-2327. (b) Kubo, Y.; Tsukahara, M.; Ishihara, S.; Tokita, S. Chem. Commun. 2000, 653-654. (c) Gunnlaugsson, T.; Davis, A. P.; Glynn, M. Chem. Commun. 2001, 2556-2557. (d) Sasaki, S.; Citterio, D.; Ozawa, S.; Suzuki, K. J. Chem. Soc., Perkin Trans. 2 2001, 2309-2313. (e) Nishizawa, S.; Cui, Y.-Y.; Minagawa, M.; Morita, K.; Kato, Y.; Taniguchi, S.; Kato, R.; Teramae, N. J. Chem. Soc., Perkin Trans. 2 2002, 866-870.
98. III centers also absorb in the UV, see e.g., Goodall, W.; Williams, J. A. G. J. Chem. Soc., Dalton Trans. 2000, 2893-2895. Sun, S. S.; Lees, A. J.; Zavalij, P. Y. Inorg. Chem. 2003, 42, 3445-3453.
99. III centers also absorb in the UV, see e.g., Goodall, W.; Williams, J. A. G. J. Chem. Soc., Dalton Trans. 2000, 2893-2895. Sun, S. S.; Lees, A. J.; Zavalij, P. Y. Inorg. Chem. 2003, 42, 3445-3453.
100. III centers also absorb in the UV, see e.g., Goodall, W.; Williams, J. A. G. J. Chem. Soc., Dalton Trans. 2000, 2893-2895. Sun, S. S.; Lees, A. J.; Zavalij, P. Y. Inorg. Chem. 2003, 42, 3445-3453.
101. III centers also absorb in the UV, see e.g., Goodall, W.; Williams, J. A. G. J. Chem. Soc., Dalton Trans. 2000, 2893-2895. Sun, S. S.; Lees, A. J.; Zavalij, P. Y. Inorg. Chem. 2003, 42, 3445-3453.
102. 13b,d,f
103. Fitzmaurice, R. J.; Kyne, G. M.; Douhert, D.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1 2002, 841-864. Sensor molecules that were designed for short-chain dicarboxylates, basically α,ω-dicarboxylates, usually have additional signaling modes available, based on geometrical changes upon complexation of the guest, see e.g., refs 13c,f,h,m,n.
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105. PET processes can occur as pure redox processes or can involve the cotransfer of a proton, exemplifying the special case of proton-coupled electron transfer (PCET), see Cukier, R. I.; Nocera, D. G. Annu. Rev. Phys. Chem. 1998, 49, 337-369. Lebeau, E. L.; Binstead, R. A.; Meyer, T. J. J. Am. Chem. Soc. 2001, 123, 10535-10544.
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173. It should be noted that this research area is rapidly expanding at present, with first reports on e.g. organic-metalloorganic hybrid sensor materials (Das, G.; Onouchi, H.; Yashima, E.; Sakai, N.; Matile, S. ChemBioChem 2002, 3, 1089-1096.), hybrid photoactive switches (Yagi, S.; Minami, N.; Fujita, J.; Hyodo, Y.; Nakazumi, H.; Yazawa, T.; Kami, T.; Hyder Ali, A. Chem. Commun. 2002, 2444-2445.) or electrochemical sensing materials based on porous silicas and functionalized with organic groups (Jiménez-Morales, A.; Galván, J. C.; Aranda, P. Electrochim. Acta 2002, 47, 2281-2287.) having been published lately.
174. It should be noted that this research area is rapidly expanding at present, with first reports on e.g. organic-metalloorganic hybrid sensor materials (Das, G.; Onouchi, H.; Yashima, E.; Sakai, N.; Matile, S. ChemBioChem 2002, 3, 1089-1096.), hybrid photoactive switches (Yagi, S.; Minami, N.; Fujita, J.; Hyodo, Y.; Nakazumi, H.; Yazawa, T.; Kami, T.; Hyder Ali, A. Chem. Commun. 2002, 2444-2445.) or electrochemical sensing materials based on porous silicas and functionalized with organic groups (Jiménez-Morales, A.; Galván, J. C.; Aranda, P. Electrochim. Acta 2002, 47, 2281-2287.) having been published lately.
175. It should be noted that this research area is rapidly expanding at present, with first reports on e.g. organic-metalloorganic hybrid sensor materials (Das, G.; Onouchi, H.; Yashima, E.; Sakai, N.; Matile, S. ChemBioChem 2002, 3, 1089-1096.), hybrid photoactive switches (Yagi, S.; Minami, N.; Fujita, J.; Hyodo, Y.; Nakazumi, H.; Yazawa, T.; Kami, T.; Hyder Ali, A. Chem. Commun. 2002, 2444-2445.) or electrochemical sensing materials based on porous silicas and functionalized with organic groups (Jiménez-Morales, A.; Galván, J. C.; Aranda, P. Electrochim. Acta 2002, 47, 2281-2287.) having been published lately.
176. 37c The use of rigid fluorophores seems thus to be advisable.
177. El Haskouri, J.; Ortiz de Zárate, D.; Guillem, C.; LaTorre, J.; Caldés, M.; Beltrán, A.; Beltrán, D.; Descalzo, A. B.; Rodríguez-López, G.; Martínez-Máñez, R.; Marcos, M. D.; Amorós, P. Chem. Commun. 2002, 330-331.
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180. Employing the AMI method, dipole moments of 6.2 D (1), 5.2 D (3), 6.7 D (4), 7.2 D (5) are calculated for the optimized ground-state geometries of the dyes discussed here.
181. Representative data of the model compounds are included in Table 3. A detailed account on the photophysical mechanisms in 7-substituted phenoxazin-3-ones including a variety of other model compounds such as differently alkylated amines and julolidyl derivatives will be published separately, Descalzo, A. B.; Martínez-Máñez, R.; Radeglia, R.; Rurack, K.; Soto, J.; Weisshoff, H., manuscript in preparation.
182. Rettig, W. Top. Curr. Chem. 1994, 169, 253-299. Rettig, W.; Rurack, K.;
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186. Sarkar, N.; Das, K.; Nath, D. N.; Bhattacharyya, K. Langmuir 1994, 10, 326-329. Datta, A.; Mandal, D.; Pal, S. K.; Bhattacharyya, K. J. Phys. Chem. B 1997, 101, 10221-10225. Krishna, M. M. G. J. Phys. Chem. A 1999, 103, 3589-3595.
187. Schwarzenbach, G.; Mohler, H.; Sorge, J. Helv. Chim. Acta 1938, 21, 1636-1645. Vittum, P. W.; Brown, G. H. J. Am. Chem. Soc. 1946, 68, 2235-2239. Adachi, M.; Murata, Y.; Nakamura, S. J. Am. Chem. Soc. 1993, 115, 4331-4338. Morley, J. O.; Fitton, A. L. J. Phys. Chem. A 1999, 103, 11442-11450.
188. Schwarzenbach, G.; Mohler, H.; Sorge, J. Helv. Chim. Acta 1938, 21, 1636-1645. Vittum, P. W.; Brown, G. H. J. Am. Chem. Soc. 1946, 68, 2235-2239. Adachi, M.; Murata, Y.; Nakamura, S. J. Am. Chem. Soc. 1993, 115, 4331-4338. Morley, J. O.; Fitton, A. L. J. Phys. Chem. A 1999, 103, 11442-11450.
189. Schwarzenbach, G.; Mohler, H.; Sorge, J. Helv. Chim. Acta 1938, 21, 1636-1645. Vittum, P. W.; Brown, G. H. J. Am. Chem. Soc. 1946, 68, 2235-2239. Adachi, M.; Murata, Y.; Nakamura, S. J. Am. Chem. Soc. 1993, 115, 4331-4338. Morley, J. O.; Fitton, A. L. J. Phys. Chem. A 1999, 103, 11442-11450.
190. Schwarzenbach, G.; Mohler, H.; Sorge, J. Helv. Chim. Acta 1938, 21, 1636-1645. Vittum, P. W.; Brown, G. H. J. Am. Chem. Soc. 1946, 68, 2235-2239. Adachi, M.; Murata, Y.; Nakamura, S. J. Am. Chem. Soc. 1993, 115, 4331-4338. Morley, J. O.; Fitton, A. L. J. Phys. Chem. A 1999, 103, 11442-11450.
191. Viscosity data taken from CRC Handbook of Chemistry and Physics; Lide, D. R., Ed.; CRC Press: Boca Raton, 1993, 73rd ed., pp 6-166-6-170.
192. -1.
193. Similar trends are found for the model compounds in ref 67.
194. Dähne, S.; Leupold, D.; Nikolajewski, H.-E.; Radeglia, R. Z. Naturforsch. 1965, 20b, 1006-1007. Radeglia, R.; Dähne, S. J. Mol. Struct. 1970, 5, 399-411. Benniston, A. C.; Harriman, A.; McAvoy, C. J. Chem. Soc., Faraday Trans. 1998, 94, 519-525. Boldrini, B.; Cavalli, E.; Painelli, A.; Terenziani, F. J. Phys. Chem. A 2002, 106, 6286-6294.
195. Dähne, S.; Leupold, D.; Nikolajewski, H.-E.; Radeglia, R. Z. Naturforsch. 1965, 20b, 1006-1007. Radeglia, R.; Dähne, S. J. Mol. Struct. 1970, 5, 399-411. Benniston, A. C.; Harriman, A.; McAvoy, C. J. Chem. Soc., Faraday Trans. 1998, 94, 519-525. Boldrini, B.; Cavalli, E.; Painelli, A.; Terenziani, F. J. Phys. Chem. A 2002, 106, 6286-6294.
196. Dähne, S.; Leupold, D.; Nikolajewski, H.-E.; Radeglia, R. Z. Naturforsch. 1965, 20b, 1006-1007. Radeglia, R.; Dähne, S. J. Mol. Struct. 1970, 5, 399-411. Benniston, A. C.; Harriman, A.; McAvoy, C. J. Chem. Soc., Faraday Trans. 1998, 94, 519-525. Boldrini, B.; Cavalli, E.; Painelli, A.; Terenziani, F. J. Phys. Chem. A 2002, 106, 6286-6294.
197. Dähne, S.; Leupold, D.; Nikolajewski, H.-E.; Radeglia, R. Z. Naturforsch. 1965, 20b, 1006-1007. Radeglia, R.; Dähne, S. J. Mol. Struct. 1970, 5, 399-411. Benniston, A. C.; Harriman, A.; McAvoy, C. J. Chem. Soc., Faraday Trans. 1998, 94, 519-525. Boldrini, B.; Cavalli, E.; Painelli, A.; Terenziani, F. J. Phys. Chem. A 2002, 106, 6286-6294.
198. The reduction in emissivity in apolar solvents is most probably connected to enhanced intersystem crossing, which has been reported for related acridines and phenoxazines before (Huber, J. R.; Mantulin, W. W. J. Am. Chem. Soc. 1972, 94, 3755-3760. Kellmann, A. J. Phys. Chem. 1977, 81, 1195-1198. Kasama, K.; Kikuchi, K.; Yamamoto, S.; Ujiie, K.; Nishida, Y.; Kokubun, H. J. Phys. Chem. 1981, 85, 1291-1296.). As this effect is unimportant for the sensor qualities and performance of 1, the reader is referred to ref 67 for a more detailed description.
199. The reduction in emissivity in apolar solvents is most probably connected to enhanced intersystem crossing, which has been reported for related acridines and phenoxazines before (Huber, J. R.; Mantulin, W. W. J. Am. Chem. Soc. 1972, 94, 3755-3760. Kellmann, A. J. Phys. Chem. 1977, 81, 1195-1198. Kasama, K.; Kikuchi, K.; Yamamoto, S.; Ujiie, K.; Nishida, Y.; Kokubun, H. J. Phys. Chem. 1981, 85, 1291-1296.). As this effect is unimportant for the sensor qualities and performance of 1, the reader is referred to ref 67 for a more detailed description.
200. The reduction in emissivity in apolar solvents is most probably connected to enhanced intersystem crossing, which has been reported for related acridines and phenoxazines before (Huber, J. R.; Mantulin, W. W. J. Am. Chem. Soc. 1972, 94, 3755-3760. Kellmann, A. J. Phys. Chem. 1977, 81, 1195-1198. Kasama, K.; Kikuchi, K.; Yamamoto, S.; Ujiie, K.; Nishida, Y.; Kokubun, H. J. Phys. Chem. 1981, 85, 1291-1296.). As this effect is unimportant for the sensor qualities and performance of 1, the reader is referred to ref 67 for a more detailed description.
201. Hibbert, F.; Emsley, J. Adv. Phys. Org. Chem. 1990, 26, 255-379 and references therein.
202. - species can be observed. For further discussions, see Tabata, M.; Kaneko, K.; Murakami, Y.; Hisaeda, Y.; Mimura, H. Microchem. J. 1994, 49, 136-144, Gunnlaugsson, T.; Kruger, P. E.; Jensen, P.; Pfeffer, F. M.; Hussey, G. M. Tetrahedron Lett. 2003, 44, 8909-8913, Lee, J. Y.; Cho, E. J.; Mukamel, S.; Nam, K. C. J. Org. Chem. 2004, 69, 943-950 and refs 12e and 13q.
203. - species can be observed. For further discussions, see Tabata, M.; Kaneko, K.; Murakami, Y.; Hisaeda, Y.; Mimura, H. Microchem. J. 1994, 49, 136-144, Gunnlaugsson, T.; Kruger, P. E.; Jensen, P.; Pfeffer, F. M.; Hussey, G. M. Tetrahedron Lett. 2003, 44, 8909-8913, Lee, J. Y.; Cho, E. J.; Mukamel, S.; Nam, K. C. J. Org. Chem. 2004, 69, 943-950 and refs 12e and 13q.
204. - species can be observed. For further discussions, see Tabata, M.; Kaneko, K.; Murakami, Y.; Hisaeda, Y.; Mimura, H. Microchem. J. 1994, 49, 136-144, Gunnlaugsson, T.; Kruger, P. E.; Jensen, P.; Pfeffer, F. M.; Hussey, G. M. Tetrahedron Lett. 2003, 44, 8909-8913, Lee, J. Y.; Cho, E. J.; Mukamel, S.; Nam, K. C. J. Org. Chem. 2004, 69, 943-950 and refs 12e and 13q.
205. - species can be observed. For further discussions, see Tabata, M.; Kaneko, K.; Murakami, Y.; Hisaeda, Y.; Mimura, H. Microchem. J. 1994, 49, 136-144, Gunnlaugsson, T.; Kruger, P. E.; Jensen, P.; Pfeffer, F. M.; Hussey, G. M. Tetrahedron Lett. 2003, 44, 8909-8913, Lee, J. Y.; Cho, E. J.; Mukamel, S.; Nam, K. C. J. Org. Chem. 2004, 69, 943-950 and refs 12e and 13q.
206. - species can be observed. For further discussions, see Tabata, M.; Kaneko, K.; Murakami, Y.; Hisaeda, Y.; Mimura, H. Microchem. J. 1994, 49, 136-144, Gunnlaugsson, T.; Kruger, P. E.; Jensen, P.; Pfeffer, F. M.; Hussey, G. M. Tetrahedron Lett. 2003, 44, 8909-8913, Lee, J. Y.; Cho, E. J.; Mukamel, S.; Nam, K. C. J. Org. Chem. 2004, 69, 943-950 and refs 12e and 13q.
207. - species can be observed. For further discussions, see Tabata, M.; Kaneko, K.; Murakami, Y.; Hisaeda, Y.; Mimura, H. Microchem. J. 1994, 49, 136-144, Gunnlaugsson, T.; Kruger, P. E.; Jensen, P.; Pfeffer, F. M.; Hussey, G. M. Tetrahedron Lett. 2003, 44, 8909-8913, Lee, J. Y.; Cho, E. J.; Mukamel, S.; Nam, K. C. J. Org. Chem. 2004, 69, 943-950 and refs 12e and 13q.
208. - species can be observed. For further discussions, see Tabata, M.; Kaneko, K.; Murakami, Y.; Hisaeda, Y.; Mimura, H. Microchem. J. 1994, 49, 136-144, Gunnlaugsson, T.; Kruger, P. E.; Jensen, P.; Pfeffer, F. M.; Hussey, G. M. Tetrahedron Lett. 2003, 44, 8909-8913, Lee, J. Y.; Cho, E. J.; Mukamel, S.; Nam, K. C. J. Org. Chem. 2004, 69, 943-950 and refs 12e and 13q.
209. - species can be observed. For further discussions, see Tabata, M.; Kaneko, K.; Murakami, Y.; Hisaeda, Y.; Mimura, H. Microchem. J. 1994, 49, 136-144, Gunnlaugsson, T.; Kruger, P. E.; Jensen, P.; Pfeffer, F. M.; Hussey, G. M. Tetrahedron Lett. 2003, 44, 8909-8913, Lee, J. Y.; Cho, E. J.; Mukamel, S.; Nam, K. C. J. Org. Chem. 2004, 69, 943-950 and refs 12e and 13q.
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214. In fact, 1 does not respond to any analyte in water, including the now well-solvated fluoride ion.
215. No change in the reaction mixture occurred upon heating of 2 with benzyl bromide in dry EtOH at 60°C under Ar atmosphere for several hours. Altering the conditions to heating 2 in anhydrous DMF with an excess of 5 equivalents of pentyl bromide under Ar atmosphere for more than 24 h did also not result in a success when following the advance of the reaction by TLC.
216. - showed excellent stability over a testing period of 9 months. Furthermore, M1Me stored floating on water over that period of time also did not show any reduced performance.
217. Descalzo, A. B.; Martínez-Máñez, R.; Rurack, K.; Amorós, P. Manuscript in preparation.
218. Recently, Mizutani et al. found a comparable enhancement of the binding constant of a supramolecular host-guest system due to increased hydrophobic interaction for alkyl chain-appended porphyrin frameworks, Mizutani, T.; Kozake, K.; Wada, K.; Kitagawa, S. Chem. Commun. 2003, 2918-2919.
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223. Quasi-continuous refers to the finite number of single lifetimes that the software employed allows to fit to a given set of data. In our case, with the FLA900 program package allowing to include between 20 and 100 lifetimes, we obtained the best results with the maximum number of lifetimes. Representative examples of fits are given in Figure S9.
224. Overall binding refers to the macroscopically measurable apparent binding constant. At present, we cannot resolve which of the microscopic processes - uptake of the carboxylate, binding at the hydrophobic inner wall - accounts for this behavior.
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