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University of Oregon

1. White, Brittany. The Synthesis of Functionalized Cycloparaphenylenes as Novel Biocompatible Fluorescent Probes and Organic Materials.

Degree: 2019, University of Oregon

Conjugated macrocycles have emerged as novel structural motifs that modulate the electronic properties of organic molecules because of their strained and contorted structures. Cycloparaphenylenes, known as nanohoops, are a particularly attractive scaffold for the design of new types of carbon nanomaterials because of their size-selective synthesis, radially oriented π-systems and tunable electronic properties. The development of modular syntheses of nanohoops over the past decade should enable the preparation of substituted derivatives that can be tuned for applications in biology and materials science. Chapter I provides a brief overview of conjugated macrocycles recently reported in the literature with a discussion of the structural effects that are responsible for the remarkable properties of this class of molecules. Chapter II highlights a scalable and mild synthetic approach developed in our lab to prepare nanohoop conjugated macrocycles and expands the generality of this methodology with the formal synthesis of natural product Acerogenin E. Chapter III describes the synthesis of cycloparaphenylenes with versatile functional handles and uncovers the reactivity of the strain nanohoop backbone under reaction conditions that promote the formation of radical cations. Chapter IV takes advantage of the functional groups described in chapter III to develop the first example of nanohoops as a new class of biocompatible fluorophores. Chapter V details a novel synthetic approach that enables the incorporation of the linear acene pentacene into the nanohoop backbone and reports our findings on the impact that the macrocyclic structure has on the properties of this organic semiconductor. In summary, the findings discussed in this dissertation provide synthetic strategies for the selective functionalization of nanohoops and highlight this class of molecules as a novel scaffold for the design of new types of carbon nanomaterials. This dissertation includes previously published and unpublished co-authored material. Advisors/Committee Members: Jasti, Ramesh (advisor).

Subjects/Keywords: Biocompatible fluorophores; Nanohoops; Organic materials; Physical organic chemistry; Synthetic chemistry

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

White, B. (2019). The Synthesis of Functionalized Cycloparaphenylenes as Novel Biocompatible Fluorescent Probes and Organic Materials. (Thesis). University of Oregon. Retrieved from http://hdl.handle.net/1794/24521

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16th Edition):

White, Brittany. “The Synthesis of Functionalized Cycloparaphenylenes as Novel Biocompatible Fluorescent Probes and Organic Materials.” 2019. Thesis, University of Oregon. Accessed December 07, 2019. http://hdl.handle.net/1794/24521.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7th Edition):

White, Brittany. “The Synthesis of Functionalized Cycloparaphenylenes as Novel Biocompatible Fluorescent Probes and Organic Materials.” 2019. Web. 07 Dec 2019.

Vancouver:

White B. The Synthesis of Functionalized Cycloparaphenylenes as Novel Biocompatible Fluorescent Probes and Organic Materials. [Internet] [Thesis]. University of Oregon; 2019. [cited 2019 Dec 07]. Available from: http://hdl.handle.net/1794/24521.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

White B. The Synthesis of Functionalized Cycloparaphenylenes as Novel Biocompatible Fluorescent Probes and Organic Materials. [Thesis]. University of Oregon; 2019. Available from: http://hdl.handle.net/1794/24521

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

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