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Designing Molecular Assemblies in the Solid-State: Induced-Stacking by a Rebek Cleft

Published online by Cambridge University Press:  21 March 2011

Leonard R. MacGillivray  and
Michelle M. Siebke
Leonard R. MacGillivray
Affiliation:
Department of Chemistry, University of Iowa Iowa City, IA USA 52242-1294
Michelle M. Siebke
Affiliation:
Department of Chemistry, University of Iowa Iowa City, IA USA 52242-1294
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Abstract

Co-crystallization of 2,7-di-tert-butyl-9,9-dimethyl-4,5-xanthenedicarboxylic acid (1), a Rebek cleft, with 1,2-trans-bis(4-pyridyl)ethylene 2 yields a four-component molecular assembly, 2(1)·2(2), that is held together by four O-H…N hydrogen bonds. The cleft organizes the bipyridine such that two molecules of 2 lie in a stacked arrangement.

Type
Research Article
Information
MRS Online Proceedings Library (OPL) , Volume 676: Symposium Y – Synthesis, Functional Properties and Applications of Nanostructures , 2001 , Y2.8
Copyright
Copyright © Materials Research Society 2001

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References

REFERENCES

1. Drexler, K. E., Molecular Engineering: An Approach to the Development of General Capabilities for Molecular Manipulation. Proc. Natl. Acad. Sci. USA 78, 5275 (1981).Google Scholar
2. Drexler, K.E., Engines of Creation. The Coming Era of Nanotechnology. (Anchor Books, 1990).Google Scholar
3. Nicolau, K. C., Vourloumis, D., Winssinger, N. and Baran, P. S., The Art and Science of Total Synthesis at the Dawn of the Twenty-First Century, Angew. Chem., Int. Ed. Engl. 39, 44 (2000).Google Scholar
4. Lehn, J. -M., Supramolecular Chemistry (Wiley-VCH, 1995).Google Scholar
5. MacGillivray, L. R., Reid, J. L. and Ripmeester, J. A., Supramolecular Control of Reactivity in the Solid State Using Linear Molecular Templates. J. Am. Chem. Soc. 122, 7817 (2000).Google Scholar
6. Anderson, S. and Anderson, H.L. in Templated Organic Synthesis, edited by Diederich, F., F., and Stang, P. J., (Wiley-VCH, 2000) pp. 1–38.Google Scholar
7. MacGillivray, L. R., Siebke, M. M. and Reid, J. L., Co-Planar Recognition by a Rebek Cleft is Provided by Cooperative Structural Effects involving a Combination of O-H…O, O-H…N, and C-H…O Forces, Org. Lett., in press.Google Scholar
8. MacGillivray, L. R. and Siebke, M. M., Crystal and Molecular Structure of 2,7-di-tert-butyl-9,9-dimethyl-4,5-xanthenedicarboxylic acid, J. Chem. Crystallogr., in press.Google Scholar
9. Sheldrick, G. M., Acta. Crystallogr. A 46, 467 (1990).Google Scholar
10. Sheldrick, G. M., SHELXL93, University of Göttingen (1993).Google Scholar
11. Barbour, L. J., RES2INS, Program for Graphic Representation of SHELXL Instruction Files. University of Missouri-Columbia (1997).Google Scholar
12. C -O bond distances [C-O distances (Å): C(1)-O(1) 1.239(4), C(1)-O(2) 1.235(4), C(15)-O(3) 1.318(4), C(15)-O(4) 1.187(4), C(38)-O(6) 1.327(4), C(38)-O(7) 1.202(4), C(52)-O(8) 1.297(4), C(52)-O(9) 1.218(4)] and angles [O-C-O angles (°): O(1)-C(1)-O(2) 125.6(3), O(3)-C(15)-O(4) 125.1(3), O(6)-C(38)-O(7) 123.5(3), O(8)-C(52)-O(9) 123.6(3)[ suggest that the acid form of 1 exists in 2(1).2(3).Google Scholar
13. Schmidt, G. M. J., Photodimerization in the Solid State, Pure Appl. Chem. 27, 647 (1971).Google Scholar
14. Desiraju, G. R. and Gavezzotti, A., From molecular to crystal structure; polynuclear aromatic hydrocarbons. J. Chem. Soc., Chem. Commun. 621 (1989).Google Scholar