Award Abstract #0615049
Cucurbit[10]uril

NSF Org:	CHE Division of Chemistry
Initial Amendment Date:	June 2, 2006
Latest Amendment Date:	July 1, 2008
Award Number:	0615049
Award Instrument:	Continuing grant
Program Manager:	Tyrone D. Mitchell CHE Division of Chemistry MPS Directorate for Mathematical & Physical Sciences
Start Date:	June 15, 2006
Expires:	May 31, 2009 (Estimated)
Awarded Amount to Date:	$432390
Investigator(s):	Lyle Isaacs Lisaacs@umd.edu (Principal Investigator)
Sponsor:	University of Maryland College Park 3112 LEE BLDG COLLEGE PARK, MD 20742 301/405-6269
NSF Program(s):	OTHER GLOBAL LEARNING & TRNING, BIMOLECULAR PROCESSES, UNIMOLECULAR PROCESSES
Field Application(s):
Program Reference Code(s):	OTHR,9183,5979,5946,0000
Program Element Code(s):	7731,1944,1942

ABSTRACT

With this new award, the Organic and Macromolecular Chemistry Program supports the work of Professor Lyle D. Isaacs of the Chemistry Department at the University of Maryland, College Park, MD. This research will investigate the use of cucurbit[10]uril (CB[10]), the largest cucurbit[n]uril known, as a molecular container in aqueous solution. In particular, the use of CB[10] as molecular chaperone to control the folding of melamine oligomers into well-defined conformations will be explored. In addition, complexes between CB[10] and cationic (metallo)porphyrins will be prepared and their use in forming termolecular complexes with suitable molecular guests will be investigated. The CB[10]-porphyrin complexes will also be applied as catalysts for oxidation reactions in water. This project will also investigate the possibility of allosteric control of the macromolecular conformation of cationic calixarenes inside CB[10] by the introduction of small molecules.

These experiments will evaluate the potential for cucurbiturils to function as real-world molecular containers for applications such as drug delivery. This project will foster the training of students at all academic levels, including a number from underrepresented groups, as interdisciplinary scientists.

PUBLICATIONS PRODUCED AS A RESULT OF THIS RESEARCH

(Showing: 1 - 9 of 9).

Chakrabarti, S.; Mukhopadhyay, P.; Lin, S.; Isaacs, L..  "Reconfigurable Four Component Molecular Switch Based on pH-Controlled Guest Swapping.,"  Org. Lett.,  v.9,  2007,  p. 2349.

Chen, Y.; She, N.; Meng, X.; Yin, G.; Wu, A.; Isaacs, L..  "Chiral Molecular Clips Control Hierarchical Crystalline Organization.,"  Org. Lett.,  v.9,  2007,  p. 1899.

Huang, W.-H.; Liu, S.; Zavalij, P. Y.; Isaacs, L..  "Nor-Seco-Cucurbit[10]uril Exhibits Homotropic Allosterism.,"  J. Am. Chem. Soc.,  v.128,  2006,  p. 14744.

Huang, W.-H.; Zavalij, P. Y.; Isaacs, L..  "Chiral Recognition Inside a Chiral Cucurbituril.,"  Angew. Chem. Int. Ed.,  v.46,  2007,  p. 7425.

Huang, W.-H.; Zavalij, P. Y.; Isaacs, L..  "Cucurbit[6]uril-Phenylenediammonium Diiodide Decahydrate Inclusion Complex.,"  Acta Crystallogr., Sect. E,  v.E63,  2007,  p. o1060.

Liu, S.; Kim, K.; Isaacs, L..  "Mechanism of the Conversion of Inverted CB[6] to CB[6].,"  J. Org. Chem.,  v.72,  2007,  p. 7425.

Liu, S.; Zavalij, P. Y.; Lam, Y.-F.; Isaacs, L..  "Refolding Foldamers: Triazene-Arylene Oligomers that Change Shape with Chemical Stimuli.,"  J. Am. Chem. Soc.,  v.129,  2007,  p. 11232.

Mukhopadhyay, P.; Zavalij, P. Y.; Isaacs, L..  "High Fidelity Kinetic Self-Sorting in Multi-Component Systems Based on Guests with Multiple,"  J. Am. Chem. Soc.,  v.128,  2006,  p. 14093.

Rekharsky, M. V.; Mori, T.; Yang, C.; Ko, Y. H.; Selvapalam, N.; Kim, H.; Sobransingh, D.; Kaifer, A. E.; Liu, S.; Isaacs, L.; Chen, W.; Gilson, M. K.; Kim, K.; Inoue, Y..  "A Synthetic Host-Guest System Achieves Biotin-Avidin Affinity by Overcoming Enthalpy-Entropy Compensation.,"  Proc. Natl. Acad. Sci. USA,  v.104,  2007,  p. 20737.


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