ORGN 265 |
| The control of [2+2] photoreativity in the solid state is of great interest. In recent years, we have demonstrated that template-directed synthesis in the solid state can be utilized to prepare biologically relevant molecular targets quantitatively and in a stereocontrolled manner1,2. To explore the robustness of our method, we have introduced various functional groups (e.g. electron-donating, electron-accepting) to the pyridine functionality of the reaction precursor (i.e. olefin). In particular, we have synthesized four 4-styrylpyridines and trans-1,2-bis(4-pyridyl)ethylenes with methyl- and chloro-substituents on the ortho position of the pyridyl functionality (Scheme 1). These reaction precursors were successfully utilized to form discrete four-component hydrogen-bonded assemblies with various linear templates (i.e. resorcinol derivatives). Photoreactivity and 1H NMR studies of all assemblies revealed a quantitative conversion of their reaction precursors to the corresponding cyclobutane derivatives and thereby suggests that our synthetic approach is tolerant to structural modifications to the precursor molecules. Ref. (1) Friscic, T; MacGillivray, L. R. Chem. Commun. 2003, 11, 1306-1307. (2) Xiuchun, G; Friscic T; MacGillivray L. R. Angew. Chem. Int. Ed. 2004, 43, 232-236.
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Molecular Recognition and Self Assembly
1:00 PM-4:40 PM, Monday, April 7, 2008 Morial Convention Center -- Rm. R04, Oral
Division of Organic Chemistry |
