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Title:Hydrogen bond mediated self-assembly: Solid state structures and synthesis of building blocks
Author(s):Fenlon, Edward Emmett
Doctoral Committee Chair(s):Zimmerman, Steven C.
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:Ph.D.
Genre:Dissertation
Subject(s):Chemistry, Organic
Chemistry, Physical
Abstract:The X-ray structure of a trimesic acid$\bullet$pyrene$\bullet$ethanol cocrystal is described. The "chicken-wire" network found in trimesic acid was expanded through ethanol bridging of some of the hydrogen bonded carboxylic acid dimers. The expanded chicken wire networks of the structure do not interpenetrate. The Cambridge Crystallographic Data File (CCDF) was searched to determine the ratio of hydroxy bridge carboxylic acids to standard dimers. Standard dimers represented 93%, singly bridged dimers 1%, and doubly bridged dimers 6% of the total number of hits.
The five step synthesis of bis-guanine 78, potentially capable of forming a helical aggregate with bis-cytosine 88, is described. The X-ray crystal structure of bis-cytosine 88 is presented.
The design and synthesis of 1,7,10-anthyridin-6(7H)-one 123a and pyrido- (3,2-g) -pteridin-4(3H)-one 150, each capable of forming cyclic hydrogen bonded hexamers are described. Several 1,7,10-anthyridines were prepared. The final step in the syntheses was a double ring annulation by a Friedlander-like condensation between 2,6-diaminopyridine-3-carboxaldehyde and methyl 3,5-dioxo-5-amino pentanoate. The synthesis of pyrido- (3,2-g) -pteridin-4(3H)-one 150 required 14 steps and proceeded in 3.3% yield. The convergent step in the synthesis was a Timmis condensation between 6-amino-2-(methylthio)-5-nitroso-pyrimidin-4-one and nitrile 134 to form pterin 146. Preliminary gel permeation chromatography (GPC) studies suggest that 150 forms a discrete aggregate in methylene chloride and tetrahydrofuran.
Issue Date:1995
Type:Text
Language:English
URI:http://hdl.handle.net/2142/21003
Rights Information:Copyright 1995 Fenlon, Edward Emmett
Date Available in IDEALS:2011-05-07
Identifier in Online Catalog:AAI9624344
OCLC Identifier:(UMI)AAI9624344


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