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Zimmerman, Steven C. Baloga, Monica Helaine 2011-05-07T13:07:41Z 2011-05-07T13:07:41Z 10000-01-01 1995 Part I. Three molecular tweezers have been synthesized to determine the role of preorganization in the host-guest complexation of these systems. The synthesis of these tweezers was accomplished by the reaction of their respective dibromo-pyrylium salts with an absolute ethanol/aqueous ammonium hydroxide solution followed by a lithium/halogen exchange and addition of dimethoxyacridone chromophores. Tweezers 11-13 have zero, one, and two additional degrees of free rotation, respectively, which lessens the enforced syn cofacial orientation of the diacridine chromophores and the overall rigidity of the system. $\sp1$H NMR binding studies indicate an increase in the association constant (K$\sb{a}$) with the increase in rigidity. The effects of increasing rigidity are additive with $\rm\Delta\Delta G\sp\circ\sb{13\to11}=2\Delta\Delta G\sp\circ\sb{13\to12}$ = 1.8 kcal$\cdot$mol$\sp{-1}$. Thus, the enforced syn orientation of 11 provides no special benefit other than its role in preorganizing the host. In addition, progress towards the synthesis of a water soluble molecular tweezer containing unsubstituted phenanthridinium chromophores is described. Part II. Several classes of guest molecules present a complex three dimensional array of hydrogen bond donor and acceptor groups. In such cases a more empirical approach to host design may be most effective. We describe a rapid synthesis of bis(amidonaphthyridine) receptors by Friedlander condensations using various diketone precursors (i.e. 1,3-diacetyl benzene and 1,1$\sp\prime$-diacetyl ferrocene) and 2,6-diaminopyridine-3-carboxaldehyde (36). Complexation studies are reported including HPLC analysis of these receptors on glucose-bonded stationary phases. Made available in DSpace on 2011-05-07T13:07:41Z (GMT). No. of bitstreams: 2 license.txt: 4922 bytes, checksum: 910b249b4beec47e7ab768910c8f966f (MD5) 9543524.pdf: 4117709 bytes, checksum: 368e4a0881b891c4e568f71acdadbed6 (MD5) Previous issue date: 1995 Item marked as restricted to the 'UIUC Users [automated]' Group (id=2) by Howard Ding (hding2@illinois.edu) on 2011-05-07T14:50:33Z Item is restricted indefinitely. Restriction data tranferred 2014-07-01T11:23:06-05:00 Original Data Group with Access UIUC Users [automated] Release Date: none Reason: ETDs are only available to UIUC Users without author permission ETDs are only available to UIUC Users without author permission U of I Only AAI9543524 (UMI)AAI9543524 http://hdl.handle.net/2142/21404 eng Copyright 1995 Baloga, Monica Helaine Chemistry, Organic Part I. Molecular tweezers: Role of preorganization and synthetic progress toward a water soluble tweezer. Part II. Progress towards an empirical approach to carbohydrate recognition text Chemistry Chemistry University of Illinois at Urbana-Champaign Dissertation Ph.D.