Synthesis and solid-state organization of coil-ring-coil block copolymers

Chemistry - A European Journal

Volumn 9, Issue 15, 2003, Pages 3481-3491

  Rosselli, Silvia ^a   Ramminger, Anne Désirée ^a   Wagner, Thomas ^a   Lieser, Günter ^a   Höger, Sigurd ^a,b  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

^b UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

Macrocycles; Nanostructures; Polymers; Supramolecular chemistry

Indexed keywords

HYDROXYLATION; OLIGOMERS; OXIDATION; POLYSTYRENES; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS (CHEMICAL);

SOLID-STATE ORGANIZATION;

BLOCK COPOLYMERS;

COPOLYMER; CYCLOHEXANE; MACROCYCLIC COMPOUND; POLYSTYRENE;

ARTICLE; COVALENT BOND; CRYSTALLIZATION; ELECTRON DIFFRACTION; HOLLOW FIBER; NANOPARTICLE; PHASE SEPARATION; SAMPLING; SOLID STATE; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS;

EID: 0041529982     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200304796     Document Type: Article

References (62)

1. For some recent examples of complex superstructures formed by rod-coil block copolymers see, for example: a) E. R. Zubarev, M. U. Pralle, L. Li, S. I. Stupp, Science 1999, 283, 523-526; b) J. T. Chen, E. L. Thomas, C. K. Ober, G.-P. Mao, Science 1996, 273, 343-346; c) S. A. Jenekhe, X. L. Chen, Science 1999, 283, 372-375; d) H.-A. Klok, J. F. Langenwalter, S. Lecommandoux, Macromolecules 2000, 33, 7819-7826; e) H. Engelkamp, S. Middelbeek, R. J. M. Nolte, Science 1999, 284, 785-788; f) M. Lee, Y.-S. Jeong, B.-K. Cho, N.-K. Oh, W.-C. Zin, Chem. Eur. J. 2002, 8, 876-883; g) J. Raez, I. Manners, M. A. Winnik, J. Am. Chem. Soc. 2002, 124, 10381-10395.
2. For some recent examples of complex superstructures formed by rod-coil block copolymers see, for example: a) E. R. Zubarev, M. U. Pralle, L. Li, S. I. Stupp, Science 1999, 283, 523-526; b) J. T. Chen, E. L. Thomas, C. K. Ober, G.-P. Mao, Science 1996, 273, 343-346; c) S. A. Jenekhe, X. L. Chen, Science 1999, 283, 372-375; d) H.-A. Klok, J. F. Langenwalter, S. Lecommandoux, Macromolecules 2000, 33, 7819-7826; e) H. Engelkamp, S. Middelbeek, R. J. M. Nolte, Science 1999, 284, 785-788; f) M. Lee, Y.-S. Jeong, B.-K. Cho, N.-K. Oh, W.-C. Zin, Chem. Eur. J. 2002, 8, 876-883; g) J. Raez, I. Manners, M. A. Winnik, J. Am. Chem. Soc. 2002, 124, 10381-10395.
3. For some recent examples of complex superstructures formed by rod-coil block copolymers see, for example: a) E. R. Zubarev, M. U. Pralle, L. Li, S. I. Stupp, Science 1999, 283, 523-526; b) J. T. Chen, E. L. Thomas, C. K. Ober, G.-P. Mao, Science 1996, 273, 343-346; c) S. A. Jenekhe, X. L. Chen, Science 1999, 283, 372-375; d) H.-A. Klok, J. F. Langenwalter, S. Lecommandoux, Macromolecules 2000, 33, 7819-7826; e) H. Engelkamp, S. Middelbeek, R. J. M. Nolte, Science 1999, 284, 785-788; f) M. Lee, Y.-S. Jeong, B.-K. Cho, N.-K. Oh, W.-C. Zin, Chem. Eur. J. 2002, 8, 876-883; g) J. Raez, I. Manners, M. A. Winnik, J. Am. Chem. Soc. 2002, 124, 10381-10395.
4. For some recent examples of complex superstructures formed by rod-coil block copolymers see, for example: a) E. R. Zubarev, M. U. Pralle, L. Li, S. I. Stupp, Science 1999, 283, 523-526; b) J. T. Chen, E. L. Thomas, C. K. Ober, G.-P. Mao, Science 1996, 273, 343-346; c) S. A. Jenekhe, X. L. Chen, Science 1999, 283, 372-375; d) H.-A. Klok, J. F. Langenwalter, S. Lecommandoux, Macromolecules 2000, 33, 7819-7826; e) H. Engelkamp, S. Middelbeek, R. J. M. Nolte, Science 1999, 284, 785-788; f) M. Lee, Y.-S. Jeong, B.-K. Cho, N.-K. Oh, W.-C. Zin, Chem. Eur. J. 2002, 8, 876-883; g) J. Raez, I. Manners, M. A. Winnik, J. Am. Chem. Soc. 2002, 124, 10381-10395.
5. For some recent examples of complex superstructures formed by rod-coil block copolymers see, for example: a) E. R. Zubarev, M. U. Pralle, L. Li, S. I. Stupp, Science 1999, 283, 523-526; b) J. T. Chen, E. L. Thomas, C. K. Ober, G.-P. Mao, Science 1996, 273, 343-346; c) S. A. Jenekhe, X. L. Chen, Science 1999, 283, 372-375; d) H.-A. Klok, J. F. Langenwalter, S. Lecommandoux, Macromolecules 2000, 33, 7819-7826; e) H. Engelkamp, S. Middelbeek, R. J. M. Nolte, Science 1999, 284, 785-788; f) M. Lee, Y.-S. Jeong, B.-K. Cho, N.-K. Oh, W.-C. Zin, Chem. Eur. J. 2002, 8, 876-883; g) J. Raez, I. Manners, M. A. Winnik, J. Am. Chem. Soc. 2002, 124, 10381-10395.
6. For some recent examples of complex superstructures formed by rod-coil block copolymers see, for example: a) E. R. Zubarev, M. U. Pralle, L. Li, S. I. Stupp, Science 1999, 283, 523-526; b) J. T. Chen, E. L. Thomas, C. K. Ober, G.-P. Mao, Science 1996, 273, 343-346; c) S. A. Jenekhe, X. L. Chen, Science 1999, 283, 372-375; d) H.-A. Klok, J. F. Langenwalter, S. Lecommandoux, Macromolecules 2000, 33, 7819-7826; e) H. Engelkamp, S. Middelbeek, R. J. M. Nolte, Science 1999, 284, 785-788; f) M. Lee, Y.-S. Jeong, B.-K. Cho, N.-K. Oh, W.-C. Zin, Chem. Eur. J. 2002, 8, 876-883; g) J. Raez, I. Manners, M. A. Winnik, J. Am. Chem. Soc. 2002, 124, 10381-10395.
7. For some recent examples of complex superstructures formed by rod-coil block copolymers see, for example: a) E. R. Zubarev, M. U. Pralle, L. Li, S. I. Stupp, Science 1999, 283, 523-526; b) J. T. Chen, E. L. Thomas, C. K. Ober, G.-P. Mao, Science 1996, 273, 343-346; c) S. A. Jenekhe, X. L. Chen, Science 1999, 283, 372-375; d) H.-A. Klok, J. F. Langenwalter, S. Lecommandoux, Macromolecules 2000, 33, 7819-7826; e) H. Engelkamp, S. Middelbeek, R. J. M. Nolte, Science 1999, 284, 785-788; f) M. Lee, Y.-S. Jeong, B.-K. Cho, N.-K. Oh, W.-C. Zin, Chem. Eur. J. 2002, 8, 876-883; g) J. Raez, I. Manners, M. A. Winnik, J. Am. Chem. Soc. 2002, 124, 10381-10395.
8. Reviews about rod-coil block copolymers: a) M. Lee, B.-K. Cho, W.-C. Zin, Chem. Rev. 2001, 101, 3869-3892; b) H.-A. Klok, S. Lecommandoux, Adv. Mater. 2001, 13, 1217-1229; c) G. Mao, C. K. Ober, Acta Polymer. 1997, 48, 405-422.
9. Reviews about rod-coil block copolymers: a) M. Lee, B.-K. Cho, W.-C. Zin, Chem. Rev. 2001, 101, 3869-3892; b) H.-A. Klok, S. Lecommandoux, Adv. Mater. 2001, 13, 1217-1229; c) G. Mao, C. K. Ober, Acta Polymer. 1997, 48, 405-422.
10. Reviews about rod-coil block copolymers: a) M. Lee, B.-K. Cho, W.-C. Zin, Chem. Rev. 2001, 101, 3869-3892; b) H.-A. Klok, S. Lecommandoux, Adv. Mater. 2001, 13, 1217-1229; c) G. Mao, C. K. Ober, Acta Polymer. 1997, 48, 405-422.
11. a) S. Rosselli, A.-D. Ramminger, T. Wagner, B. Silier, S. Wiegand, W. Häußler, G. Lieser, V. Scheumann, S. Höger, Angew. Chem. 2001,113, 3234-3237; Angew. Chem. Int. Ed. 2001, 40, 3138-3141;
12. a) S. Rosselli, A.-D. Ramminger, T. Wagner, B. Silier, S. Wiegand, W. Häußler, G. Lieser, V. Scheumann, S. Höger, Angew. Chem. 2001,113, 3234-3237; Angew. Chem. Int. Ed. 2001, 40, 3138-3141;
13. b) S. Höger, K. Bonrad, S. Rosselli, A.-D. Ramminger, T. Wagner, B. Silier, S. Wiegand, W. Häußler, G. Lieser, V. Scheumann, Macromol. Symp. 2002, 177, 185-191.
14. Reviews about shape-persistent macrocycles: a) J. S. Moore, Acc. Chem. Res. 1997, 30, 402-413; b) S. Höger, J. Polym. Sci, Part A 1999, 37, 2685-2698; c) M. M. Haley, J. J. Pak, S. C. Brand, Topic Curr. Chem. 1999, 201, 81-130; d) C. Grave, A. D. Schlüter, Eur. J. Org. Chem. 2002, 3075-3098.
15. Reviews about shape-persistent macrocycles: a) J. S. Moore, Acc. Chem. Res. 1997, 30, 402-413; b) S. Höger, J. Polym. Sci, Part A 1999, 37, 2685-2698; c) M. M. Haley, J. J. Pak, S. C. Brand, Topic Curr. Chem. 1999, 201, 81-130; d) C. Grave, A. D. Schlüter, Eur. J. Org. Chem. 2002, 3075-3098.
16. Reviews about shape-persistent macrocycles: a) J. S. Moore, Acc. Chem. Res. 1997, 30, 402-413; b) S. Höger, J. Polym. Sci, Part A 1999, 37, 2685-2698; c) M. M. Haley, J. J. Pak, S. C. Brand, Topic Curr. Chem. 1999, 201, 81-130; d) C. Grave, A. D. Schlüter, Eur. J. Org. Chem. 2002, 3075-3098.
17. Reviews about shape-persistent macrocycles: a) J. S. Moore, Acc. Chem. Res. 1997, 30, 402-413; b) S. Höger, J. Polym. Sci, Part A 1999, 37, 2685-2698; c) M. M. Haley, J. J. Pak, S. C. Brand, Topic Curr. Chem. 1999, 201, 81-130; d) C. Grave, A. D. Schlüter, Eur. J. Org. Chem. 2002, 3075-3098.
18. For the concept of intraannular functional groups, see, for example: a) F. Vögtle, P. Neumann, Tetrahedron 1970, 26, 5299-5318; b) E. Weber, F. Vögtle, Chem. Ber. 1976, 109, 1803-1831.
19. For the concept of intraannular functional groups, see, for example: a) F. Vögtle, P. Neumann, Tetrahedron 1970, 26, 5299-5318; b) E. Weber, F. Vögtle, Chem. Ber. 1976, 109, 1803-1831.
20. For shape-persistent macrocycles containing intraannular functional groups, see, for example: a) H. L. Anderson, J. K. M. Sanders, J. Chem. Soc. Chem. Commun. 1992, 946-947; b) S. Anderson, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722-1726; Angew. Chem. Int. Ed. Engl. 1995, 34, 1596-1600; c) D. L. Morrison, S. Höger, J. Chem. Soc. Chem. Commun. 1996, 2313-2314; d) Y. Tobe, N. Utsumi, K. Kawabata, A. Nagano, K. Naemura, Angew. Chem. 1998, 110, 1347-1349; Angew. Chem. Int. Ed. Engl. 1998, 37, 1285-1287; e) S. Höger, A.-D. Meckenstock, Chem. Eur. J. 1999, 5, 1686-1691; f) U. Lehman, A.D. Schlüter, Eur. J. Org. Chem. 2000, 3483-3487; g) Y. Hosokawa, T. Kawase, M. Oda, J. Chem. Soc. Chem. Commun. 2001, 1948-1949; h) M. Fischer, S. Höger, Eur. J. Org. Chem. 2003, 441-446.
21. For shape-persistent macrocycles containing intraannular functional groups, see, for example: a) H. L. Anderson, J. K. M. Sanders, J. Chem. Soc. Chem. Commun. 1992, 946-947; b) S. Anderson, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722-1726; Angew. Chem. Int. Ed. Engl. 1995, 34, 1596-1600; c) D. L. Morrison, S. Höger, J. Chem. Soc. Chem. Commun. 1996, 2313-2314; d) Y. Tobe, N. Utsumi, K. Kawabata, A. Nagano, K. Naemura, Angew. Chem. 1998, 110, 1347-1349; Angew. Chem. Int. Ed. Engl. 1998, 37, 1285-1287; e) S. Höger, A.-D. Meckenstock, Chem. Eur. J. 1999, 5, 1686-1691; f) U. Lehman, A.D. Schlüter, Eur. J. Org. Chem. 2000, 3483-3487; g) Y. Hosokawa, T. Kawase, M. Oda, J. Chem. Soc. Chem. Commun. 2001, 1948-1949; h) M. Fischer, S. Höger, Eur. J. Org. Chem. 2003, 441-446.
22. For shape-persistent macrocycles containing intraannular functional groups, see, for example: a) H. L. Anderson, J. K. M. Sanders, J. Chem. Soc. Chem. Commun. 1992, 946-947; b) S. Anderson, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722-1726; Angew. Chem. Int. Ed. Engl. 1995, 34, 1596-1600; c) D. L. Morrison, S. Höger, J. Chem. Soc. Chem. Commun. 1996, 2313-2314; d) Y. Tobe, N. Utsumi, K. Kawabata, A. Nagano, K. Naemura, Angew. Chem. 1998, 110, 1347-1349; Angew. Chem. Int. Ed. Engl. 1998, 37, 1285-1287; e) S. Höger, A.-D. Meckenstock, Chem. Eur. J. 1999, 5, 1686-1691; f) U. Lehman, A.D. Schlüter, Eur. J. Org. Chem. 2000, 3483-3487; g) Y. Hosokawa, T. Kawase, M. Oda, J. Chem. Soc. Chem. Commun. 2001, 1948-1949; h) M. Fischer, S. Höger, Eur. J. Org. Chem. 2003, 441-446.
23. For shape-persistent macrocycles containing intraannular functional groups, see, for example: a) H. L. Anderson, J. K. M. Sanders, J. Chem. Soc. Chem. Commun. 1992, 946-947; b) S. Anderson, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722-1726; Angew. Chem. Int. Ed. Engl. 1995, 34, 1596-1600; c) D. L. Morrison, S. Höger, J. Chem. Soc. Chem. Commun. 1996, 2313-2314; d) Y. Tobe, N. Utsumi, K. Kawabata, A. Nagano, K. Naemura, Angew. Chem. 1998, 110, 1347-1349; Angew. Chem. Int. Ed. Engl. 1998, 37, 1285-1287; e) S. Höger, A.-D. Meckenstock, Chem. Eur. J. 1999, 5, 1686-1691; f) U. Lehman, A.D. Schlüter, Eur. J. Org. Chem. 2000, 3483-3487; g) Y. Hosokawa, T. Kawase, M. Oda, J. Chem. Soc. Chem. Commun. 2001, 1948-1949; h) M. Fischer, S. Höger, Eur. J. Org. Chem. 2003, 441-446.
24. For shape-persistent macrocycles containing intraannular functional groups, see, for example: a) H. L. Anderson, J. K. M. Sanders, J. Chem. Soc. Chem. Commun. 1992, 946-947; b) S. Anderson, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722-1726; Angew. Chem. Int. Ed. Engl. 1995, 34, 1596-1600; c) D. L. Morrison, S. Höger, J. Chem. Soc. Chem. Commun. 1996, 2313-2314; d) Y. Tobe, N. Utsumi, K. Kawabata, A. Nagano, K. Naemura, Angew. Chem. 1998, 110, 1347-1349; Angew. Chem. Int. Ed. Engl. 1998, 37, 1285-1287; e) S. Höger, A.-D. Meckenstock, Chem. Eur. J. 1999, 5, 1686-1691; f) U. Lehman, A.D. Schlüter, Eur. J. Org. Chem. 2000, 3483-3487; g) Y. Hosokawa, T. Kawase, M. Oda, J. Chem. Soc. Chem. Commun. 2001, 1948-1949; h) M. Fischer, S. Höger, Eur. J. Org. Chem. 2003, 441-446.
25. For shape-persistent macrocycles containing intraannular functional groups, see, for example: a) H. L. Anderson, J. K. M. Sanders, J. Chem. Soc. Chem. Commun. 1992, 946-947; b) S. Anderson, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722-1726; Angew. Chem. Int. Ed. Engl. 1995, 34, 1596-1600; c) D. L. Morrison, S. Höger, J. Chem. Soc. Chem. Commun. 1996, 2313-2314; d) Y. Tobe, N. Utsumi, K. Kawabata, A. Nagano, K. Naemura, Angew. Chem. 1998, 110, 1347-1349; Angew. Chem. Int. Ed. Engl. 1998, 37, 1285-1287; e) S. Höger, A.-D. Meckenstock, Chem. Eur. J. 1999, 5, 1686-1691; f) U. Lehman, A.D. Schlüter, Eur. J. Org. Chem. 2000, 3483-3487; g) Y. Hosokawa, T. Kawase, M. Oda, J. Chem. Soc. Chem. Commun. 2001, 1948-1949; h) M. Fischer, S. Höger, Eur. J. Org. Chem. 2003, 441-446.
26. For shape-persistent macrocycles containing intraannular functional groups, see, for example: a) H. L. Anderson, J. K. M. Sanders, J. Chem. Soc. Chem. Commun. 1992, 946-947; b) S. Anderson, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722-1726; Angew. Chem. Int. Ed. Engl. 1995, 34, 1596-1600; c) D. L. Morrison, S. Höger, J. Chem. Soc. Chem. Commun. 1996, 2313-2314; d) Y. Tobe, N. Utsumi, K. Kawabata, A. Nagano, K. Naemura, Angew. Chem. 1998, 110, 1347-1349; Angew. Chem. Int. Ed. Engl. 1998, 37, 1285-1287; e) S. Höger, A.-D. Meckenstock, Chem. Eur. J. 1999, 5, 1686-1691; f) U. Lehman, A.D. Schlüter, Eur. J. Org. Chem. 2000, 3483-3487; g) Y. Hosokawa, T. Kawase, M. Oda, J. Chem. Soc. Chem. Commun. 2001, 1948-1949; h) M. Fischer, S. Höger, Eur. J. Org. Chem. 2003, 441-446.
27. For shape-persistent macrocycles containing intraannular functional groups, see, for example: a) H. L. Anderson, J. K. M. Sanders, J. Chem. Soc. Chem. Commun. 1992, 946-947; b) S. Anderson, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722-1726; Angew. Chem. Int. Ed. Engl. 1995, 34, 1596-1600; c) D. L. Morrison, S. Höger, J. Chem. Soc. Chem. Commun. 1996, 2313-2314; d) Y. Tobe, N. Utsumi, K. Kawabata, A. Nagano, K. Naemura, Angew. Chem. 1998, 110, 1347-1349; Angew. Chem. Int. Ed. Engl. 1998, 37, 1285-1287; e) S. Höger, A.-D. Meckenstock, Chem. Eur. J. 1999, 5, 1686-1691; f) U. Lehman, A.D. Schlüter, Eur. J. Org. Chem. 2000, 3483-3487; g) Y. Hosokawa, T. Kawase, M. Oda, J. Chem. Soc. Chem. Commun. 2001, 1948-1949; h) M. Fischer, S. Höger, Eur. J. Org. Chem. 2003, 441-446.
28. For shape-persistent macrocycles containing intraannular functional groups, see, for example: a) H. L. Anderson, J. K. M. Sanders, J. Chem. Soc. Chem. Commun. 1992, 946-947; b) S. Anderson, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722-1726; Angew. Chem. Int. Ed. Engl. 1995, 34, 1596-1600; c) D. L. Morrison, S. Höger, J. Chem. Soc. Chem. Commun. 1996, 2313-2314; d) Y. Tobe, N. Utsumi, K. Kawabata, A. Nagano, K. Naemura, Angew. Chem. 1998, 110, 1347-1349; Angew. Chem. Int. Ed. Engl. 1998, 37, 1285-1287; e) S. Höger, A.-D. Meckenstock, Chem. Eur. J. 1999, 5, 1686-1691; f) U. Lehman, A.D. Schlüter, Eur. J. Org. Chem. 2000, 3483-3487; g) Y. Hosokawa, T. Kawase, M. Oda, J. Chem. Soc. Chem. Commun. 2001, 1948-1949; h) M. Fischer, S. Höger, Eur. J. Org. Chem. 2003, 441-446.
29. For shape-persistent macrocycles containing intraannular functional groups, see, for example: a) H. L. Anderson, J. K. M. Sanders, J. Chem. Soc. Chem. Commun. 1992, 946-947; b) S. Anderson, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722-1726; Angew. Chem. Int. Ed. Engl. 1995, 34, 1596-1600; c) D. L. Morrison, S. Höger, J. Chem. Soc. Chem. Commun. 1996, 2313-2314; d) Y. Tobe, N. Utsumi, K. Kawabata, A. Nagano, K. Naemura, Angew. Chem. 1998, 110, 1347-1349; Angew. Chem. Int. Ed. Engl. 1998, 37, 1285-1287; e) S. Höger, A.-D. Meckenstock, Chem. Eur. J. 1999, 5, 1686-1691; f) U. Lehman, A.D. Schlüter, Eur. J. Org. Chem. 2000, 3483-3487; g) Y. Hosokawa, T. Kawase, M. Oda, J. Chem. Soc. Chem. Commun. 2001, 1948-1949; h) M. Fischer, S. Höger, Eur. J. Org. Chem. 2003, 441-446.
30. For channel structures based on shape-persistent macrocycles see for example: a) D. Venkataraman, S. Lee, J. Zhang, J. S. Moore, Nature 1994, 371, 591-593; b) D. T. Bong, T. D. Clark, J. R. Granja, M. R. Ghadiri, Angew. Chem. 2001, 113, 1016-1041; Angew. Chem. Int. Ed. Engl. 2001, 40, 988-1011; c) G. Gattuso, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Wiliams, Angew. Chem. 1997, 107, 1615-1617; Angew. Chem. Int. Ed. Engl. 1997, 36, 1451-1454; d) O. Henze, D. Lentz, A. D. Schlüter, Chem. Eur. J. 2000, 6, 2362-2367; e) P. Müller, I. Usón, V. Hensel, A. D. Schlüter, G. M. Sheldrick, Helv. Chim. Acta 2001, 84, 778-785; f) R. A. Pascal, Jr., L. Barnett, X. Qiao, D. M. Ho, J. Org. Chem. 2000, 65, 7711-7717; g) S. Höger, D. L. Morrison, V. Enkelmann, J. Am. Chem. Soc. 2002, 124, 6734-6736.
31. For channel structures based on shape-persistent macrocycles see for example: a) D. Venkataraman, S. Lee, J. Zhang, J. S. Moore, Nature 1994, 371, 591-593; b) D. T. Bong, T. D. Clark, J. R. Granja, M. R. Ghadiri, Angew. Chem. 2001, 113, 1016-1041; Angew. Chem. Int. Ed. Engl. 2001, 40, 988-1011; c) G. Gattuso, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Wiliams, Angew. Chem. 1997, 107, 1615-1617; Angew. Chem. Int. Ed. Engl. 1997, 36, 1451-1454; d) O. Henze, D. Lentz, A. D. Schlüter, Chem. Eur. J. 2000, 6, 2362-2367; e) P. Müller, I. Usón, V. Hensel, A. D. Schlüter, G. M. Sheldrick, Helv. Chim. Acta 2001, 84, 778-785; f) R. A. Pascal, Jr., L. Barnett, X. Qiao, D. M. Ho, J. Org. Chem. 2000, 65, 7711-7717; g) S. Höger, D. L. Morrison, V. Enkelmann, J. Am. Chem. Soc. 2002, 124, 6734-6736.
32. For channel structures based on shape-persistent macrocycles see for example: a) D. Venkataraman, S. Lee, J. Zhang, J. S. Moore, Nature 1994, 371, 591-593; b) D. T. Bong, T. D. Clark, J. R. Granja, M. R. Ghadiri, Angew. Chem. 2001, 113, 1016-1041; Angew. Chem. Int. Ed. Engl. 2001, 40, 988-1011; c) G. Gattuso, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Wiliams, Angew. Chem. 1997, 107, 1615-1617; Angew. Chem. Int. Ed. Engl. 1997, 36, 1451-1454; d) O. Henze, D. Lentz, A. D. Schlüter, Chem. Eur. J. 2000, 6, 2362-2367; e) P. Müller, I. Usón, V. Hensel, A. D. Schlüter, G. M. Sheldrick, Helv. Chim. Acta 2001, 84, 778-785; f) R. A. Pascal, Jr., L. Barnett, X. Qiao, D. M. Ho, J. Org. Chem. 2000, 65, 7711-7717; g) S. Höger, D. L. Morrison, V. Enkelmann, J. Am. Chem. Soc. 2002, 124, 6734-6736.
33. For channel structures based on shape-persistent macrocycles see for example: a) D. Venkataraman, S. Lee, J. Zhang, J. S. Moore, Nature 1994, 371, 591-593; b) D. T. Bong, T. D. Clark, J. R. Granja, M. R. Ghadiri, Angew. Chem. 2001, 113, 1016-1041; Angew. Chem. Int. Ed. Engl. 2001, 40, 988-1011; c) G. Gattuso, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Wiliams, Angew. Chem. 1997, 107, 1615-1617; Angew. Chem. Int. Ed. Engl. 1997, 36, 1451-1454; d) O. Henze, D. Lentz, A. D. Schlüter, Chem. Eur. J. 2000, 6, 2362-2367; e) P. Müller, I. Usón, V. Hensel, A. D. Schlüter, G. M. Sheldrick, Helv. Chim. Acta 2001, 84, 778-785; f) R. A. Pascal, Jr., L. Barnett, X. Qiao, D. M. Ho, J. Org. Chem. 2000, 65, 7711-7717; g) S. Höger, D. L. Morrison, V. Enkelmann, J. Am. Chem. Soc. 2002, 124, 6734-6736.
34. For channel structures based on shape-persistent macrocycles see for example: a) D. Venkataraman, S. Lee, J. Zhang, J. S. Moore, Nature 1994, 371, 591-593; b) D. T. Bong, T. D. Clark, J. R. Granja, M. R. Ghadiri, Angew. Chem. 2001, 113, 1016-1041; Angew. Chem. Int. Ed. Engl. 2001, 40, 988-1011; c) G. Gattuso, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Wiliams, Angew. Chem. 1997, 107, 1615-1617; Angew. Chem. Int. Ed. Engl. 1997, 36, 1451-1454; d) O. Henze, D. Lentz, A. D. Schlüter, Chem. Eur. J. 2000, 6, 2362-2367; e) P. Müller, I. Usón, V. Hensel, A. D. Schlüter, G. M. Sheldrick, Helv. Chim. Acta 2001, 84, 778-785; f) R. A. Pascal, Jr., L. Barnett, X. Qiao, D. M. Ho, J. Org. Chem. 2000, 65, 7711-7717; g) S. Höger, D. L. Morrison, V. Enkelmann, J. Am. Chem. Soc. 2002, 124, 6734-6736.
35. For channel structures based on shape-persistent macrocycles see for example: a) D. Venkataraman, S. Lee, J. Zhang, J. S. Moore, Nature 1994, 371, 591-593; b) D. T. Bong, T. D. Clark, J. R. Granja, M. R. Ghadiri, Angew. Chem. 2001, 113, 1016-1041; Angew. Chem. Int. Ed. Engl. 2001, 40, 988-1011; c) G. Gattuso, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Wiliams, Angew. Chem. 1997, 107, 1615-1617; Angew. Chem. Int. Ed. Engl. 1997, 36, 1451-1454; d) O. Henze, D. Lentz, A. D. Schlüter, Chem. Eur. J. 2000, 6, 2362-2367; e) P. Müller, I. Usón, V. Hensel, A. D. Schlüter, G. M. Sheldrick, Helv. Chim. Acta 2001, 84, 778-785; f) R. A. Pascal, Jr., L. Barnett, X. Qiao, D. M. Ho, J. Org. Chem. 2000, 65, 7711-7717; g) S. Höger, D. L. Morrison, V. Enkelmann, J. Am. Chem. Soc. 2002, 124, 6734-6736.
36. For channel structures based on shape-persistent macrocycles see for example: a) D. Venkataraman, S. Lee, J. Zhang, J. S. Moore, Nature 1994, 371, 591-593; b) D. T. Bong, T. D. Clark, J. R. Granja, M. R. Ghadiri, Angew. Chem. 2001, 113, 1016-1041; Angew. Chem. Int. Ed. Engl. 2001, 40, 988-1011; c) G. Gattuso, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Wiliams, Angew. Chem. 1997, 107, 1615-1617; Angew. Chem. Int. Ed. Engl. 1997, 36, 1451-1454; d) O. Henze, D. Lentz, A. D. Schlüter, Chem. Eur. J. 2000, 6, 2362-2367; e) P. Müller, I. Usón, V. Hensel, A. D. Schlüter, G. M. Sheldrick, Helv. Chim. Acta 2001, 84, 778-785; f) R. A. Pascal, Jr., L. Barnett, X. Qiao, D. M. Ho, J. Org. Chem. 2000, 65, 7711-7717; g) S. Höger, D. L. Morrison, V. Enkelmann, J. Am. Chem. Soc. 2002, 124, 6734-6736.
37. For channel structures based on shape-persistent macrocycles see for example: a) D. Venkataraman, S. Lee, J. Zhang, J. S. Moore, Nature 1994, 371, 591-593; b) D. T. Bong, T. D. Clark, J. R. Granja, M. R. Ghadiri, Angew. Chem. 2001, 113, 1016-1041; Angew. Chem. Int. Ed. Engl. 2001, 40, 988-1011; c) G. Gattuso, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Wiliams, Angew. Chem. 1997, 107, 1615-1617; Angew. Chem. Int. Ed. Engl. 1997, 36, 1451-1454; d) O. Henze, D. Lentz, A. D. Schlüter, Chem. Eur. J. 2000, 6, 2362-2367; e) P. Müller, I. Usón, V. Hensel, A. D. Schlüter, G. M. Sheldrick, Helv. Chim. Acta 2001, 84, 778-785; f) R. A. Pascal, Jr., L. Barnett, X. Qiao, D. M. Ho, J. Org. Chem. 2000, 65, 7711-7717; g) S. Höger, D. L. Morrison, V. Enkelmann, J. Am. Chem. Soc. 2002, 124, 6734-6736.
38. For channel structures based on shape-persistent macrocycles see for example: a) D. Venkataraman, S. Lee, J. Zhang, J. S. Moore, Nature 1994, 371, 591-593; b) D. T. Bong, T. D. Clark, J. R. Granja, M. R. Ghadiri, Angew. Chem. 2001, 113, 1016-1041; Angew. Chem. Int. Ed. Engl. 2001, 40, 988-1011; c) G. Gattuso, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Wiliams, Angew. Chem. 1997, 107, 1615-1617; Angew. Chem. Int. Ed. Engl. 1997, 36, 1451-1454; d) O. Henze, D. Lentz, A. D. Schlüter, Chem. Eur. J. 2000, 6, 2362-2367; e) P. Müller, I. Usón, V. Hensel, A. D. Schlüter, G. M. Sheldrick, Helv. Chim. Acta 2001, 84, 778-785; f) R. A. Pascal, Jr., L. Barnett, X. Qiao, D. M. Ho, J. Org. Chem. 2000, 65, 7711-7717; g) S. Höger, D. L. Morrison, V. Enkelmann, J. Am. Chem. Soc. 2002, 124, 6734-6736.
39. This is remarkable in the context that shape-persistent macrocycles of similar structure with oligo-alkyl side chains of defined length do not dissolve in this solvent. This shows the superior solubilizing properties of PS oligomers over oligo-alkyl substituents.
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