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osu1243445872.pdf (36.91 MB)
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Abstract Header
Structure-Function Studies of Modular Aromatics That Form Molecular Organogels
Author Info
Baddeley, Christopher Peter
Permalink:
http://rave.ohiolink.edu/etdc/view?acc_num=osu1243445872
Abstract Details
Year and Degree
2009, Master of Science, Ohio State University, Chemistry.
Abstract
Three urea-based aromatics 1-3, each with distinct steric and electronic characteristics, have been synthesized and their ability to undergo hierarchical assembly and gel organic solvents investigated. We have found that compound 1 promotes the sol-gel phase transition in primary alcohols (from CH3OH to C10H21OH; CGC < 15 mg/mL), while 2 and 3 do not. IR spectroscopy, X-ray powder diffraction (XRPD), and transmission electron microscopy (TEM) measurements show that 1 organizes into “cylinders” in primary alcohols, using three-centered hydrogen bonds and π-π aromatic interactions. The cylinders further organize into pairs through interdigitation of the methyl groups of the adjacent aromatic rings. Importantly, the lateral packing of the cylinders is enhanced as the bulk solvent polarity increases providing a mechanism for controlling the material’s morphology via the solvophobic effect. Molecular mechanics (Amber) and semiempirical (AM1) calculations suggested similar conformational behavior but distinct electronic properties of 1-3. Thus, π-deficient 2 without the methyl groups and π-rich 3 without aromatic nitrogen fail to promote the sol-gel phase transition in alcohols due to their inability to undergo effective hierarchical assembly, which is necessary for the formation of a 3D fibrillar network. In addition, we have found that the ultrasonication of a supersaturated solution of 1 is necessary for the gelation. Presumably, a fast exchange of the aggregates of 1 is assisted with sonic waves to allow for the effective and “error free” assembly wherein an entangled net of fibers capable of encapsulating solvent molecules is formed.
Committee
Jovica Badjic, PhD (Advisor)
Gideon Fraenkel, PhD (Committee Member)
Pages
87 p.
Subject Headings
Chemistry
Keywords
Gels
;
Gelation
;
Physical Organic
;
ChemistryGels
;
Gelation
;
Physical Organic
;
Chemistry
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Citations
Baddeley, C. P. (2009).
Structure-Function Studies of Modular Aromatics That Form Molecular Organogels
[Master's thesis, Ohio State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=osu1243445872
APA Style (7th edition)
Baddeley, Christopher.
Structure-Function Studies of Modular Aromatics That Form Molecular Organogels.
2009. Ohio State University, Master's thesis.
OhioLINK Electronic Theses and Dissertations Center
, http://rave.ohiolink.edu/etdc/view?acc_num=osu1243445872.
MLA Style (8th edition)
Baddeley, Christopher. "Structure-Function Studies of Modular Aromatics That Form Molecular Organogels." Master's thesis, Ohio State University, 2009. http://rave.ohiolink.edu/etdc/view?acc_num=osu1243445872
Chicago Manual of Style (17th edition)
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Document number:
osu1243445872
Download Count:
615
Copyright Info
© 2009, all rights reserved.
This open access ETD is published by The Ohio State University and OhioLINK.