Synthesis Of Amphiphilic Polyisoprene Terpenoid(PIPTP) Dendrons And Their Applications In OPEs

This thesis is concerned with the studies on the chemistry of synthesis of a new class of amphiphilic polyisoprene terpenoid (PIPTP) dendrons and the synthesis of "core-shells" molecular wires and their electronic properties. As well as explored the synthesis route of the Janus dendrimer. It consists of the following three parts:First, a review of literature on the synthesis of dendrimer and its derivatives was revealed. Furthermore, the importance of the amphiphilic dendrimer in self-assembly and catalytic and the recent development of the synthesis and expand of novel dendrimers was summarized.In chapter 2, the synthesis of PIPTP dendrons and their application as "shells" in molecular wires was introduced. The halogen-containing dendrimer branches and intermediate monoester or diester fragments were prepared by double-stage convergent method which improved in our group. The skeleton of PIPTP dendrons was built by double-metal alkyl addition reaction as the key steps then by dehydroxylation, hydrogenation or hydrogenolysis reactions. First studies used relatively simple fatty chain dendrimers as a pilot to explore universal route and started from bromobutane to build dendrimer skeleton by Grignard and Kagan methods as key steps respectively. The route of G4 dendron was shorter 7 steps than G3 one similar in the literature, which useful for a large number of sample preparation. Correspondingly, the G4 PIPTP dendron was prepared by 15 steps with a 10% overall yield. These PIPTP dendrons were connected with OPEs as "shells" by Sonogashira coupling reaction as key step. And the dendrimer effect of "core-shells" was proved by UV and fluorescence spectra.In Chapter 3, the synthesis of Janus dendrimer was explored. Commercial propylene glycol was selected as the starting material. Additionally, the similar synthesis method in PIPTP dendrons was used to construct multi-hydroxy substituted dendrimer, and the preliminary properties were investigated.In this paper, the PIPTP dendrons were completed and the novel Janus dendrimer work was explored, besides the unsuccessful synthesis process was summed up. Furthermore, it involved a total of 73 new compounds and solved the whole problem in the preparation of aliphatic chain dendrons. Also, it elaborated the key general synthetic method through the metal alkylation reaction and was extended to other similar dendrimer synthesis, which thus enriched he related such dendrimer synthesis.