Covalent self-assembly of a dimeric borazaaromatic macrocycle

Chemical Communications

Volumn , Issue 22, 1999, Pages 2279-2280

  Comina, Paul J ^a   Philp, Douglas ^a   Kariuki, Benson M ^a   Harris, Kenneth D M ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND; PHENANTHRENE DERIVATIVE;

ARTICLE; DEHYDRATION; ENTHALPY; ENTROPY; MOLECULAR DYNAMICS; OLIGOMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0033592810     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a906257b     Document Type: Article

References (24)

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4. D. Philp and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 1996, 35, 1154; D. S. Lawrence, T. Jiang and M. Levett, Chem. Rev., 1995, 95, 2229; J. S. Lindsey, New J. Chem., 1991, 15, 153; G. M. Whitesides, J. P. Mathias and C. T. Seto, Science, 1991, 254, 1312.
5. S. V. Kolotuchin and S. C. Zimmerman, J. Am. Chem. Soc., 1998, 120, 9092; T. Martin, U. Obst and J. Rebek, Jr, Science, 1998, 281, 1842; M. Mammen, E. I. Shakhnovich, J. M. Deutch and G. M. Whitesides, J. Org. Chem., 1998, 63, 3821; T. B. Norsten, R. McDonald and N. R. Branda, Chem. Commun., 1999, 719; M. Enomoto and T. Aida, J. Am. Chem. Soc., 1999, 121, 874.
6. S. V. Kolotuchin and S. C. Zimmerman, J. Am. Chem. Soc., 1998, 120, 9092; T. Martin, U. Obst and J. Rebek, Jr, Science, 1998, 281, 1842; M. Mammen, E. I. Shakhnovich, J. M. Deutch and G. M. Whitesides, J. Org. Chem., 1998, 63, 3821; T. B. Norsten, R. McDonald and N. R. Branda, Chem. Commun., 1999, 719; M. Enomoto and T. Aida, J. Am. Chem. Soc., 1999, 121, 874.
7. S. V. Kolotuchin and S. C. Zimmerman, J. Am. Chem. Soc., 1998, 120, 9092; T. Martin, U. Obst and J. Rebek, Jr, Science, 1998, 281, 1842; M. Mammen, E. I. Shakhnovich, J. M. Deutch and G. M. Whitesides, J. Org. Chem., 1998, 63, 3821; T. B. Norsten, R. McDonald and N. R. Branda, Chem. Commun., 1999, 719; M. Enomoto and T. Aida, J. Am. Chem. Soc., 1999, 121, 874.
8. S. V. Kolotuchin and S. C. Zimmerman, J. Am. Chem. Soc., 1998, 120, 9092; T. Martin, U. Obst and J. Rebek, Jr, Science, 1998, 281, 1842; M. Mammen, E. I. Shakhnovich, J. M. Deutch and G. M. Whitesides, J. Org. Chem., 1998, 63, 3821; T. B. Norsten, R. McDonald and N. R. Branda, Chem. Commun., 1999, 719; M. Enomoto and T. Aida, J. Am. Chem. Soc., 1999, 121, 874.
9. S. V. Kolotuchin and S. C. Zimmerman, J. Am. Chem. Soc., 1998, 120, 9092; T. Martin, U. Obst and J. Rebek, Jr, Science, 1998, 281, 1842; M. Mammen, E. I. Shakhnovich, J. M. Deutch and G. M. Whitesides, J. Org. Chem., 1998, 63, 3821; T. B. Norsten, R. McDonald and N. R. Branda, Chem. Commun., 1999, 719; M. Enomoto and T. Aida, J. Am. Chem. Soc., 1999, 121, 874.
10. Large, complex architectures can be constructed using strict self-assembly. The classical example is the Tobacco Mosaic Virus, see A. Klug, Angew. Chem., Int. Ed. Engl., 1983, 22, 565.
11. For other elegant examples of covalent self-assembly, see S. J. Rowan, P. A. Brady and J. K. M. Sanders, Angew. Chem., Int. Ed. Engl., 1996, 35, 2143; P. A. Brady and J. K. M. Sanders, Chem. Soc. Rev., 1997, 26, 327; S. J. Rowan, D. G. Hamilton, P. A. Brady and J. K. M. Sanders, J. Am. Chem. Soc., 1997, 119, 2578; S. J. Rowan and J. K. M. Sanders, J. Org. Chem., 1998, 63, 1536; S. J. Rowan, D. J. Reynolds and J. K. M. Sanders, J. Org. Chem., 1999, 64, 5804; J. Ipaktschi, R. Hosseinzadeh, P. Schlaf and E. Dreiseidler, Helv. Chim. Acta, 1998, 81, 1821; J. Ipaktschi, R. Hosseinzadeh and P. Schlaf, Angew. Chem., Int. Ed., 1999, 38, 1658. Sanders uses the term predisposition to describe the encoding of a thermodynamically-favourable oligomeric structure through the conformational properties of the monomer once incorporated into this larger structure. In this language, the conformational space which is open to monomer 1 should predispose, or encode, the formation of a particular oligomer of 1.
12. For other elegant examples of covalent self-assembly, see S. J. Rowan, P. A. Brady and J. K. M. Sanders, Angew. Chem., Int. Ed. Engl., 1996, 35, 2143; P. A. Brady and J. K. M. Sanders, Chem. Soc. Rev., 1997, 26, 327; S. J. Rowan, D. G. Hamilton, P. A. Brady and J. K. M. Sanders, J. Am. Chem. Soc., 1997, 119, 2578; S. J. Rowan and J. K. M. Sanders, J. Org. Chem., 1998, 63, 1536; S. J. Rowan, D. J. Reynolds and J. K. M. Sanders, J. Org. Chem., 1999, 64, 5804; J. Ipaktschi, R. Hosseinzadeh, P. Schlaf and E. Dreiseidler, Helv. Chim. Acta, 1998, 81, 1821; J. Ipaktschi, R. Hosseinzadeh and P. Schlaf, Angew. Chem., Int. Ed., 1999, 38, 1658. Sanders uses the term predisposition to describe the encoding of a thermodynamically-favourable oligomeric structure through the conformational properties of the monomer once incorporated into this larger structure. In this language, the conformational space which is open to monomer 1 should predispose, or encode, the formation of a particular oligomer of 1.
13. For other elegant examples of covalent self-assembly, see S. J. Rowan, P. A. Brady and J. K. M. Sanders, Angew. Chem., Int. Ed. Engl., 1996, 35, 2143; P. A. Brady and J. K. M. Sanders, Chem. Soc. Rev., 1997, 26, 327; S. J. Rowan, D. G. Hamilton, P. A. Brady and J. K. M. Sanders, J. Am. Chem. Soc., 1997, 119, 2578; S. J. Rowan and J. K. M. Sanders, J. Org. Chem., 1998, 63, 1536; S. J. Rowan, D. J. Reynolds and J. K. M. Sanders, J. Org. Chem., 1999, 64, 5804; J. Ipaktschi, R. Hosseinzadeh, P. Schlaf and E. Dreiseidler, Helv. Chim. Acta, 1998, 81, 1821; J. Ipaktschi, R. Hosseinzadeh and P. Schlaf, Angew. Chem., Int. Ed., 1999, 38, 1658. Sanders uses the term predisposition to describe the encoding of a thermodynamically-favourable oligomeric structure through the conformational properties of the monomer once incorporated into this larger structure. In this language, the conformational space which is open to monomer 1 should predispose, or encode, the formation of a particular oligomer of 1.
14. For other elegant examples of covalent self-assembly, see S. J. Rowan, P. A. Brady and J. K. M. Sanders, Angew. Chem., Int. Ed. Engl., 1996, 35, 2143; P. A. Brady and J. K. M. Sanders, Chem. Soc. Rev., 1997, 26, 327; S. J. Rowan, D. G. Hamilton, P. A. Brady and J. K. M. Sanders, J. Am. Chem. Soc., 1997, 119, 2578; S. J. Rowan and J. K. M. Sanders, J. Org. Chem., 1998, 63, 1536; S. J. Rowan, D. J. Reynolds and J. K. M. Sanders, J. Org. Chem., 1999, 64, 5804; J. Ipaktschi, R. Hosseinzadeh, P. Schlaf and E. Dreiseidler, Helv. Chim. Acta, 1998, 81, 1821; J. Ipaktschi, R. Hosseinzadeh and P. Schlaf, Angew. Chem., Int. Ed., 1999, 38, 1658. Sanders uses the term predisposition to describe the encoding of a thermodynamically-favourable oligomeric structure through the conformational properties of the monomer once incorporated into this larger structure. In this language, the conformational space which is open to monomer 1 should predispose, or encode, the formation of a particular oligomer of 1.
15. For other elegant examples of covalent self-assembly, see S. J. Rowan, P. A. Brady and J. K. M. Sanders, Angew. Chem., Int. Ed. Engl., 1996, 35, 2143; P. A. Brady and J. K. M. Sanders, Chem. Soc. Rev., 1997, 26, 327; S. J. Rowan, D. G. Hamilton, P. A. Brady and J. K. M. Sanders, J. Am. Chem. Soc., 1997, 119, 2578; S. J. Rowan and J. K. M. Sanders, J. Org. Chem., 1998, 63, 1536; S. J. Rowan, D. J. Reynolds and J. K. M. Sanders, J. Org. Chem., 1999, 64, 5804; J. Ipaktschi, R. Hosseinzadeh, P. Schlaf and E. Dreiseidler, Helv. Chim. Acta, 1998, 81, 1821; J. Ipaktschi, R. Hosseinzadeh and P. Schlaf, Angew. Chem., Int. Ed., 1999, 38, 1658. Sanders uses the term predisposition to describe the encoding of a thermodynamically-favourable oligomeric structure through the conformational properties of the monomer once incorporated into this larger structure. In this language, the conformational space which is open to monomer 1 should predispose, or encode, the formation of a particular oligomer of 1.
16. For other elegant examples of covalent self-assembly, see S. J. Rowan, P. A. Brady and J. K. M. Sanders, Angew. Chem., Int. Ed. Engl., 1996, 35, 2143; P. A. Brady and J. K. M. Sanders, Chem. Soc. Rev., 1997, 26, 327; S. J. Rowan, D. G. Hamilton, P. A. Brady and J. K. M. Sanders, J. Am. Chem. Soc., 1997, 119, 2578; S. J. Rowan and J. K. M. Sanders, J. Org. Chem., 1998, 63, 1536; S. J. Rowan, D. J. Reynolds and J. K. M. Sanders, J. Org. Chem., 1999, 64, 5804; J. Ipaktschi, R. Hosseinzadeh, P. Schlaf and E. Dreiseidler, Helv. Chim. Acta, 1998, 81, 1821; J. Ipaktschi, R. Hosseinzadeh and P. Schlaf, Angew. Chem., Int. Ed., 1999, 38, 1658. Sanders uses the term predisposition to describe the encoding of a thermodynamically-favourable oligomeric structure through the conformational properties of the monomer once incorporated into this larger structure. In this language, the conformational space which is open to monomer 1 should predispose, or encode, the formation of a particular oligomer of 1.
17. For other elegant examples of covalent self-assembly, see S. J. Rowan, P. A. Brady and J. K. M. Sanders, Angew. Chem., Int. Ed. Engl., 1996, 35, 2143; P. A. Brady and J. K. M. Sanders, Chem. Soc. Rev., 1997, 26, 327; S. J. Rowan, D. G. Hamilton, P. A. Brady and J. K. M. Sanders, J. Am. Chem. Soc., 1997, 119, 2578; S. J. Rowan and J. K. M. Sanders, J. Org. Chem., 1998, 63, 1536; S. J. Rowan, D. J. Reynolds and J. K. M. Sanders, J. Org. Chem., 1999, 64, 5804; J. Ipaktschi, R. Hosseinzadeh, P. Schlaf and E. Dreiseidler, Helv. Chim. Acta, 1998, 81, 1821; J. Ipaktschi, R. Hosseinzadeh and P. Schlaf, Angew. Chem., Int. Ed., 1999, 38, 1658. Sanders uses the term predisposition to describe the encoding of a thermodynamically-favourable oligomeric structure through the conformational properties of the monomer once incorporated into this larger structure. In this language, the conformational space which is open to monomer 1 should predispose, or encode, the formation of a particular oligomer of 1.
18. An example of this phenomenon, known as nucleation, can be seen in the assembly of oligonucleotides to form double helical structures which is essentially an all-or nothing process once a critical chain length is reached. See D. Pörschke and M. Eigen, J. Mol. Biol., 1971, 62, 361; M. E. Craig, D. M. Crothers and P. Doty, J. Mol. Biol., 1971, 62, 383.
19. An example of this phenomenon, known as nucleation, can be seen in the assembly of oligonucleotides to form double helical structures which is essentially an all-or nothing process once a critical chain length is reached. See D. Pörschke and M. Eigen, J. Mol. Biol., 1971, 62, 361; M. E. Craig, D. M. Crothers and P. Doty, J. Mol. Biol., 1971, 62, 383.
20. K. D. M. Harris, B. M. Kariuki, C. Lambropoulos, D. Philp and J. M. A. Robinson, Tetrahedron, 1997, 53, 8599; J. M. A. Robinson, B. M. Kariuki, D. Philp and K. D. M. Harris, Tetrahedron Lett., 1997, 38, 6281.
21. K. D. M. Harris, B. M. Kariuki, C. Lambropoulos, D. Philp and J. M. A. Robinson, Tetrahedron, 1997, 53, 8599; J. M. A. Robinson, B. M. Kariuki, D. Philp and K. D. M. Harris, Tetrahedron Lett., 1997, 38, 6281.
22. T. C. Bruice and F. C. Lightstone, Acc. Chem. Res., 1999, 32, 127.
23. G. Ercolani, J. Phys. Chem. B, 1998, 102, 5699; A. J. Kirby, Adv. Phys. Org. Chem., 1980, 17, 183.
24. G. Ercolani, J. Phys. Chem. B, 1998, 102, 5699; A. J. Kirby, Adv. Phys. Org. Chem., 1980, 17, 183.