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Title:Studies in molecular recognition. Part I. Expanded molecular tweezers: Design and synthesis of novel receptors. Part II. Molecular self-assembly: Use of carboxylic acids as self-assembly elements
Author(s):Reichert, David Edward Caples
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
Abstract:In Part I, the design, synthetic approaches, and complexation studies of molecular tweezers possessing spacer units $>$7 A are discussed. A general feature of these approaches is the use of the Friedlander reaction to generate the spacer unit. A tweezer utilizing 2,7-dimethoxyacridine as the chromophore with an inter-chromophore distance of 9.7 A was synthesized. This expanded tweezer was found to bind 2,4,5,7-tetranitrofluorenone (TENF) with a K$\sb{\rm a}$ $<$ 10 M$\sp{-1}$. Progress in the synthesis of a water soluble tweezer with an expanded spacer unit is also reported.
In Part II, the design and synthesis of a novel molecular tweezer which utilizes carboxylic acids as self-assembly elements is reported. The key feature of the synthesis was the Suzuki coupling of the bis(boronic acid) derived from 2,12-dibromo-7-(4$ \sp\prime$-methoxyphenyl)-5,6,8,9-tetrahydro-dibenz (c, h) acridine and 5-methylisophthalate triflate. The addition of a solubilizing group and hydrolysis of the methyl esters gave a molecular tweezer with four carboxylic acids which was soluble in organic solvents. Preliminary investigations suggest that the tweezer forms a well-defined aggregate in CH$\sb2$Cl$\sb2$.
Issue Date:1994
Type:Text
Language:English
URI:http://hdl.handle.net/2142/22668
Rights Information:Copyright 1994 Reichert, David Edward Caples
Date Available in IDEALS:2011-05-07
Identifier in Online Catalog:AAI9512525
OCLC Identifier:(UMI)AAI9512525


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