Year: 2005
Type: article
Abstract: This dissertation describes the synthesis and supramolecular chemistry of 7substituted-2,4,9-trithiaadamantanes.The structurally well-defined molecular building block was prepared by a multi-step synthesis from dimethyl malonate or diethyl malonate.A new synthetic method for the formation of a 2,4,9-trithiaadamantane ring system was developed using the combination of Lawesson's reagent and a Lewis acid.The method improved the reaction yields to 35-40%.The ethyl or methyl ester group attached to position 7 of the 2,4,9-trithiaadamantane ring was converted to other functionalities depending upon the applications.These functional groups include a carboxylic acid, an alcohol, an aldehyde, a long chain amide, and alkynes.Additionally, the introduction of a diazomethylcarbonyl group or an azidocarbonyl group produced the photolabile molecular surface anchors.2,4,9-Trithiaadamantan-7-yl-ethyne facilitated the synthesis of molecular wires via the Sonogashira cross coupling reaction with various phenyl halides.1,4-Bis((7-2,4,9-trithiaadamantyl)ethynyl) benzene, 1,4-bis(7-2,4,9trithiaadamantyl) butadiyne, S-{4-[4-[7-2,4,9-trithiaadamantylethynyl]-phenylethynyl]-phenyl} thioacetate and 4-[4-[7-2,4,9-trithiaadamantylethynyl]-phenylethynyl]-pyridine, were prepared.2,4,9-Trithiaadamantane-7-carboxylic acid octadecylamide (TPCONHC 18 ) was used as a ligand for stabilizing gold nanoparticles.Ligand exchange reaction of vi AGKNOWLEDGEMENT I would like to express my special thank to my adviser, Dr.
Author: Chalermchai Khemtong
Institution: University of Akron
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W2619767642