Part I: Crystal Engineering Using Trimesic Acid Analogs. Part II: An Extremely Stable Hydrogen-Bonded Hexamer

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.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2015

Author dc:creator

• Kolotuchin, Sergei Valentinovich

Contributors dc:contributor

• Zimmerman, Steven C.

• Chemistry, Organic

Language dc:language

eng

Identifier

(MiAaPQ)AAI9834701

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/84398