Author ORCID Identifier
Semester
Summer
Date of Graduation
2025
Document Type
Dissertation
Degree Type
PhD
College
Eberly College of Arts and Sciences
Department
Chemistry
Committee Chair
Kung Wang
Committee Co-Chair
Brian Popp
Committee Member
Brian Dolinar
Committee Member
Hacer Karatas Bristow
Committee Member
Jianhai Du
Abstract
The development of structurally defined carbon nanostructures has gained significant attention due to their unique electronic, optical, and mechanical properties. Cycloparaphenylenes (CPPs), also known as carbon nanohoops, and carbon nanobelts (CNBs) represent key molecular segments of carbon nanotubes (CNTs), offering a bottom-up approach to precise nanotube construction. This dissertation focuses on the synthesis, structural characterization, and functionalization of CPPs, as well as the development of novel synthetic pathways for CNBs. A series of functionalized CPPs, including [9]-, [12]-, [15]-, and [18]CPPs, were synthesized using a modular approach involving a Diels-Alder adduct formation followed by a Ni(cod)2/bpymediated macrocyclization reaction. The influence of precursor design, catalyst loading, and oxidative aromatization conditions on macrocyclization efficiency and product distribution was systematically investigated. Structural analysis via X-ray crystallography and spectroscopic techniques provided insights into the correlation between molecular conformation and reaction outcomes. In addition to CPP synthesis, novel methodologies for CNB construction were explored, addressing the challenges associated with strain energy and regioselective closure. Strategies leveraging sequential coupling reactions and oxidative cyclization provided access to structurally well-defined CNBs. The methodologies developed in this work not only enhance synthetic accessibility but also contribute to the broader understanding of carbon nanostructure formation. This research advances the field of nanocarbon chemistry by expanding synthetic approaches to CPPs and CNBs, offering new insights into their structural properties, and laying the groundwork for future applications in molecular electronics, optoelectronics, and nanomaterials science.
Recommended Citation
Li, Liu, "Functionalized Carbon Nanohoops: Synthesis, Structural Insights, and Pathways to Carbon Nanobelts" (2025). Graduate Theses, Dissertations, and Problem Reports. 12969.
https://researchrepository.wvu.edu/etd/12969