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Title:Part I: Crystal Engineering Using Trimesic Acid Analogs. Part II: An Extremely Stable Hydrogen-Bonded Hexamer
Author(s):Kolotuchin, Sergei Valentinovich
Doctoral Committee Chair(s):Zimmerman, Steven C.
Department / Program:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Subject(s):Chemistry, Organic
Abstract:Part II. In Part II, the design, synthesis and aggregation of pyrimido(4,5-b) (1,8) -naphthyridine-3H-4-one (1) in solution is reported. The design of self-complementary monomer 1 features a DDA and AAD motif, a low-generation dendrimer which provides suitable solubility in nonpolar organic solvents, and a 2-aminoethyl group which directs the self-assembly process of 1. The synthesis of 1 was accomplished from chloronaphthyridine 6 by a precedented nucleophilic cyclization with N-ethyl guanidine. It was found that 1 forms a hydrogen-bonded aggregate in nonpolar organic solvents, as well as in more competitive solvents such as THF and 10% (v/v) DMSO/chloroform. The results of size exclusion chromatography (SEC) with polystyrene standards, as well as comparisons with covalent dendritic control compounds 11 and 23, suggest that the aggregate is a hexamer.
Issue Date:1998
Description:140 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1998.
Other Identifier(s):(MiAaPQ)AAI9834701
Date Available in IDEALS:2015-09-25
Date Deposited:1998

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