Title page for ETD etd-11122009-160534

Type of Document Master's Thesis
Author Sandifer, Jace
Author's Email Address jsandi3@lsu.edu
URN etd-11122009-160534
Title Substituted Bis(Beta-Diketones) for Molecular Squares
Degree Master of Science (M.S.)
Department Chemistry
Advisory Committee
Advisor Name Title
Maverick, Andrew Committee Chair
Crowe, William Committee Member
Stanley, George Committee Member
  • Metal-organic macrocycles
Date of Defense 2009-11-09
Availability unrestricted
Our group has been synthesizing porous supramolecular metal-organic molecules using

multidentate β-diketones as ligands. For example, m-phenylenebis(acetylacetone) (m-pbaH2, 1)

and m-phenylenebis(dipropionylmethane) (m-pbprH2, 2) were readily converted to the molecular

squares Cu4(m-pba)4 (6) and Cu4(m-pbpr)4 (7), which bind guests such as 4,4-bpy and C60.1

However, 6 and 7 are only soluble in a few solvents, limiting their use in practical applications.

It is therefore necessary to derivatize the ligand with different functional groups in order to

improve solubility and adjust host-guest properties. Simple alkoxy derivatives should prove

useful in testing this idea as they would be relatively chemically inert and should not interfere

with reactions in their synthesis. Herein, I report synthesis of the ligands 5-MeO-m-pbaH2 (3), 5-

BuO-m-pbaH2 (4), and 2-MeO-m-pbaH2 (5). Ligand 3 was synthesized from 5-methoxy-1,3-

benzendimethanol in a two step reaction and reacted with Cu2+ to form a complex that is soluble

in CH2Cl2 and THF. X-ray analysis of this complex confirms that it is a molecular square with

the formula Cu4(5-MeO-m-pba)4 (square 8). Ligand 4 was synthesized from dimethyl 5-

hydroxyisophthalate in a three step reaction and used for the synthesis of Cu4(5-BuO-m-pba)4

(square 9). Square 9 is soluble in a wide range of solvents including CH2Cl2, CHCl3, THF, and

several benzene derivatives. Ligand 5 was synthesized from 2-methoxyisophthalic acid in a

three step reaction and used for the synthesis of Cu4(2-MeO-m-pba)4 (square 10).

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