Self-assembly is one of the common features of biological macromolecule, and frequently the super structures are made of self-complementary modules. Here complementarity refers to sizes, shapes and chemical surfaces involved in molecular recognition phenomena. In this proposal we explore the synthesis of self-complementary systems from small molecule modules whose geometry and orientation of recognition surface permits assembly into closed-shell superstructures. In this our premise is that the assembly process is most likely to yield to model systems; molecules that can be synthesized interpreted and manipulated with a high degree of structural certainty. We intend to prepare several simple modules and determine how their assembly into host species is dependent on their recognition surfaces, shapes and the presence of their respective guests. The long-term goals are to transport across membranes with these molecules, and their use as reaction chambers for the catalysis of biorelevant processes. The shorter term goals involve the application of results in two dimensional hydrogen bond arrays to the synthesis of three dimensional structures capable of reversible assembly and inclusion phenomena.
| Hooley, Richard J; Rebek Jr, Julius (2009) Chemistry and catalysis in functional cavitands. Chem Biol 16:255-64 |
| Restorp, Per; Berryman, Orion B; Sather, Aaron C et al. (2009) A synthetic receptor for hydrogen-bonding to fluorines of trifluoroborates. Chem Commun (Camb) :5692-4 |
| Hooley, Richard; Shenoy, Siddhartha; Rebek Jr, Julius (2008) Electronic and Steric Effects in Binding of Deep Cavitands. Org Lett : |
| Lledo, Agusti; Hooley, Richard J; Rebek Jr, Julius (2008) Recognition of guests by water-stabilized cavitand hosts. Org Lett 10:3669-71 |
| Podkoscielny, Dagmara; Hooley, Richard J; Rebek Jr, Julius et al. (2008) Ferrocene derivatives included in a water-soluble cavitand: are they electroinactive? Org Lett 10:2865-8 |
| Restorp, Per; Rebek Jr, Julius (2008) Reaction of isonitriles with carboxylic acids in a cavitand: observation of elusive isoimide intermediates. J Am Chem Soc 130:11850-1 |
| Barrett, Elizabeth S; Dale, Trevor J; Rebek Jr, Julius (2008) Stability, dynamics, and selectivity in the assembly of hydrogen-bonded hexameric capsules. J Am Chem Soc 130:2344-50 |
| Iwasawa, Tetsuo; Wash, Paul; Gibson, Christoph et al. (2007) Reaction of an Introverted Carboxylic Acid with Carbodiimide. Tetrahedron 63:6506-6511 |
| Ajami, Dariush; Rebek Jr, Julius (2007) Adaptations of guest and host in expanded self-assembled capsules. Proc Natl Acad Sci U S A 104:16000-3 |
| Barrett, Elizabeth S; Dale, Trevor J; Rebek Jr, Julius (2007) Assembly and exchange of resorcinarene capsules monitored by fluorescence resonance energy transfer. J Am Chem Soc 129:3818-9 |
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