University of Illinois Urbana-Champaign

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

Reichert, David Edward Caples

This item is only available for download by members of the University of Illinois community. Students, faculty, and staff at the U of I may log in with your NetID and password to view the item. If you are trying to access an Illinois-restricted dissertation or thesis, you can request a copy through your library's Inter-Library Loan office or purchase a copy directly from ProQuest.

Permalink

https://hdl.handle.net/2142/22668

Description

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
Issue Date
1994
Doctoral Committee Chair(s)
Zimmerman, Steven C.
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Language
eng
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$.
Type of Resource
text
Permalink
http://hdl.handle.net/2142/22668
Copyright and License Information
Copyright 1994 Reichert, David Edward Caples

Owning Collections

Graduate Dissertations and Theses at Illinois PRIMARY
Graduate Theses and Dissertations at Illinois
Dissertations and Theses - Chemistry