Arenediazonium salts as versatile (meso-ionic) tectons. Charge-transfer intercalates and clathrates in unusual crystalline networks self-assembled with neutral aromatic π-donors

Crystal Growth and Design

Volumn 4, Issue 3, 2004, Pages 563-571

  Lindeman, Sergey V ^a   Kochi, Jay K ^a  

^a University of Houston   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIAZONIUM COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CRYSTAL; CRYSTAL STRUCTURE; ELECTRON TRANSPORT; HYDROGEN BOND; MOLECULAR INTERACTION;

EID: 2542575453     PISSN: 15287483     EISSN: None     Source Type: Journal    
DOI: 10.1021/cg034218j     Document Type: Article

References (53)

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8. 4b to describe "...any molecule whose interactions are dominated by particular associative forces that induce the self-assembly of an organized network with specific architectural or functional features."
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10. (c) For further elaborations of tectons, see for example
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14. (b) Briegleb, G. Electronen Donator-Acceptor Komplexe; Springer: Berlin, 1961.
15. Compare: Lindeman, S. V.; Hecht, J.; Kochi, J. K. J. Am. Chem. Soc. 2003, 125, 11597.
16. For intermolecular π-interactions of aromatic donor-acceptor pairs, see (a) Badger, B.; Brocklehurst, B. Trans. Faraday Soc. 1970, 66, 2939 and related papers, (b) Fritz, H. P.; Gebauer, H.; Friedrich, P.; Ecker, P.; Artes, R.; Schubert, V. Z. Naturforsch. 1978, 33B, 498. (c) Herwig, P. T.; Enkelman, V.; Schmelz, D.; Mullen, K. Chem. Eur. J. 2000, 6, 1834.
17. For intermolecular π-interactions of aromatic donor-acceptor pairs, see (a) Badger, B.; Brocklehurst, B. Trans. Faraday Soc. 1970, 66, 2939 and related papers, (b) Fritz, H. P.; Gebauer, H.; Friedrich, P.; Ecker, P.; Artes, R.; Schubert, V. Z. Naturforsch. 1978, 33B, 498. (c) Herwig, P. T.; Enkelman, V.; Schmelz, D.; Mullen, K. Chem. Eur. J. 2000, 6, 1834.
18. For intermolecular π-interactions of aromatic donor-acceptor pairs, see (a) Badger, B.; Brocklehurst, B. Trans. Faraday Soc. 1970, 66, 2939 and related papers, (b) Fritz, H. P.; Gebauer, H.; Friedrich, P.; Ecker, P.; Artes, R.; Schubert, V. Z. Naturforsch. 1978, 33B, 498. (c) Herwig, P. T.; Enkelman, V.; Schmelz, D.; Mullen, K. Chem. Eur. J. 2000, 6, 1834.
19. See, e.g., (a) Jakubetz, W.; Schuster, P. Tetrahedron 1971, 27, 101. (b) Viswamitra, M. A.; Radhakrishnan, R.; Bandekar, J.; Desiraju, G. R. J. Am. Chem. Soc. 1993, 115, 4868. (c) Nishio, M.; Umezawa, Y.; Hirota, M.; Takeuchi, Y. Tetrahedron 1995, 51, 8665. (d) Braga, D.; Grepioni, F.; Tedesco, E. Organometallics 1998, 17, 2669.
20. See, e.g., (a) Jakubetz, W.; Schuster, P. Tetrahedron 1971, 27, 101. (b) Viswamitra, M. A.; Radhakrishnan, R.; Bandekar, J.; Desiraju, G. R. J. Am. Chem. Soc. 1993, 115, 4868. (c) Nishio, M.; Umezawa, Y.; Hirota, M.; Takeuchi, Y. Tetrahedron 1995, 51, 8665. (d) Braga, D.; Grepioni, F.; Tedesco, E. Organometallics 1998, 17, 2669.
21. See, e.g., (a) Jakubetz, W.; Schuster, P. Tetrahedron 1971, 27, 101. (b) Viswamitra, M. A.; Radhakrishnan, R.; Bandekar, J.; Desiraju, G. R. J. Am. Chem. Soc. 1993, 115, 4868. (c) Nishio, M.; Umezawa, Y.; Hirota, M.; Takeuchi, Y. Tetrahedron 1995, 51, 8665. (d) Braga, D.; Grepioni, F.; Tedesco, E. Organometallics 1998, 17, 2669.
22. See, e.g., (a) Jakubetz, W.; Schuster, P. Tetrahedron 1971, 27, 101. (b) Viswamitra, M. A.; Radhakrishnan, R.; Bandekar, J.; Desiraju, G. R. J. Am. Chem. Soc. 1993, 115, 4868. (c) Nishio, M.; Umezawa, Y.; Hirota, M.; Takeuchi, Y. Tetrahedron 1995, 51, 8665. (d) Braga, D.; Grepioni, F.; Tedesco, E. Organometallics 1998, 17, 2669.
23. See Wulfman, D. E.; Zollinger, H. in refs 1 and 2.
24. (a) Kosynkin, D.; Bockman, T. M.; Kochi, J. K. J. Am. Chem. Soc. 1997, 119, 4846.
25. (b) Bockman, T. M.; Kosynkin, D.; Kochi, J. K. J. Org. Chem. 1997, 62, 5811.
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28. Hrabie, J. A.; Srinivasan, A.; George, C.; Keefer, L. K. Tetrahedron Lett. 1998, 39, 5933.
29. - dramatically increases the stability of the salts, and these are commonly employed in laboratory practice.
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31. Groth, P. Acta Chem. Scand. 1981, A35, 541.
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33. Lindeman, S. V.; Kosynkin, D.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 13268.
34. The positions of the hydrogen atoms in all structures were normalized to a standard "neutronographic" value of the C-H bond length of 1.095 Å.
35. (a) In charge-transfer crystals, packing of the donor (D) and acceptor (A) units can occur either in two separate DDD and AAA stacks (homosoric) or single alternating DADA stacks (heterosoric). See, e.g.,
36. (b) Dahm, D. J.; Johnson, G. R.; Miles, M. G.; Wilson, J. D. J. Cryst. Mol. Struct. 1975, 5, 27.
37. Andresen, O.; Rømming, C. Acta Chem. Scand. 1962, 16, 1882.
38. Kompan, O. E.; Antipin, M. Y.; Struchkov, Y. T.; Mikhailov, I. E.; Dushenko, G. A.; Olekhnovich, L. P.; Minkin, V. I. Zh. Org. Khim. 1985, 21, 2032.
39. McGilligan, B. S.; Arnold, J.; Wilkinson, G.; Hussain-Bates B.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 1990, 2465.
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43. Alcock, N. W.; Greenhough, T. J.; Hirst, D. M.; Kemp, T. J.; Payne, D. R. J. Chem. Soc., Perkin Trans. 2 1980, 8.
44. Horan, C. J.; Barnes, C. L.; Glaser, R. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 1993, C49, 507.
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46. Barbero, M.; Crisma, M.; Degani, I.; Fochi, R.; Perracino, P. Synthesis 1998, 1171.
47. Alberti, G.; Costantino, U. Layered Solids and Their Intercalation Chemistry in Comprehensive Supramolecular Chemistry; Lehn, J.-M., Ed.; Elsevier: New York, 1996; Vol 7.
48. The formation of the charge-transfer donor/acceptor complexes in the crystals of the dinitro derivative cannot be attributed to the π-acceptor properties of the arenediazonium moiety alone (even enhanced by the presence of two nitro substituents). The majority of other arenediazonium salts do not crystallize together with organic π-donors, and the weaker π-donor/acceptor association is hardly a factor capable of the separating the ionic layers on its own. Instead, we believe that close-packing issues should be considered as a main origin of donor intercalation.
49. In the majority of aryldiazonium structures, the ionic layers partially interpenetrate in a ziplock manner (Figure 6A). This observation indicates that the size of protruding aryl groups is insufficient to provide close packing over the surface of the layers, and aryl groups from a neighboring layer enter into the voids between them (and vice versa). The efficient close packing in the ziplocked hydrophobic areas obviously depends on the match between van der Waals volumes of the aryl groups and separations between them. This is normally balanced (depending on size of anions that determines the distance between axes of the aryl groups in the ionic layers) by degree of folding of the layers and by the tilt of the aryl groups (cf. Figure 5, panels A and B). However, in the case of the bulky 3,5-dinitrosubstituted arene groups, the increased size of the groups and (consequently) decreased size of the separations between them make ziplocking between the layers less efficient. To compensate for the remaining voids between aryl groups, the preferred layered architecture must be either completely rearranged or some additional (donor) guest molecules must be incorporated to stabilize the structure. Apparently, the latter takes place in the intercalated structures in Figure 8A,B.
50. - anion from the diazonium coordination shell in the structure of p-nitrobenzenediazonium tetrafluoroborate (O⋯N distance of 2.97 Å). See Barnes, J. C.; Butler, A.; Anderson, L. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 1990, C46, 945.
51. 10
52. The solvate structure with acetonitrile is similar (albeit not isomorphous) to the structure with p-xylene in which the two solvent molecules replace each p-xylene donor moiety. The acetonitrile solvent molecules are more distant from the aromatic acceptor planes (4.06 Å), but form relatively strong H-bonds (C-H⋯N) with their edges (H⋯N 2.45 Å).
53. 35 see experimental section.