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

Kolotuchin, Sergei Valentinovich

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Description

Title

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

Author(s)

Kolotuchin, Sergei Valentinovich

Issue Date

1998

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

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.

Graduation Semester

1998

Type of Resource

text

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