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Title: Synthesis of nitrogen-containing polycyclic aromatic molecules by strain-enhanced 1,3-dipolar cycloaddition
Authors: Zhang, Xinjiang
Keywords: Science::Chemistry::Organic chemistry
Issue Date: 2023
Publisher: Nanyang Technological University
Source: Zhang, X. (2023). Synthesis of nitrogen-containing polycyclic aromatic molecules by strain-enhanced 1,3-dipolar cycloaddition. Doctoral thesis, Nanyang Technological University, Singapore.
Abstract: Nitrogen-containing polycyclic aromatic molecules (NPAMs) have attracted much attention in recent decades for their intriguing structures and properties, as well as potential to work as building blocks for the bottom-up synthesis of nitrogen-containing graphene, carbon nanotubes and fullerenes. The 1,3-dipolar cycloaddition reaction between compounds with unsaturated C-C bonds and π-extended azomethine ylide has proved to be an effective method for synthesizing NPAMs with large π-surface. However, substrate scope and yield of the reaction are limited by the low reactivity of certain unsaturated C-C bonds. In this thesis, we introduce molecular strain in these inactive substrates to promote a strain-enhanced 1,3-dipolar cycloaddition. These reactions give novel NPAMs such as azacorannulenophane and azahexabenzocoronenium with short synthetic route and improved yield. The resulting NPAMs also exhibit unique structural and physical characteristics, which provides more insights into the synthesis and properties of π-extended NPAMs.
DOI: 10.32657/10356/164623
Schools: School of Chemistry, Chemical Engineering and Biotechnology
Rights: This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License (CC BY-NC 4.0).
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:CCEB Theses

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