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Organic Chemistry

Theses/Dissertations

2016

Aromaticity

Articles 1 - 2 of 2

Full-Text Articles in Physical Sciences and Mathematics

Synthesis And Characterization Of Polycyclic Aromatic Hydrocarbon ( Pah )-Porphyrin Hybrids, Ruixiao Gao Oct 2016

Synthesis And Characterization Of Polycyclic Aromatic Hydrocarbon ( Pah )-Porphyrin Hybrids, Ruixiao Gao

Theses and Dissertations

Carbaporphyrins are porphyrin analogs where one or more pyrrole units are replaced with a carbocyclic ring. Benziporphyrins are porphyrin analogues with a 1,3-phenylene unit replacing one of the pyrrole subunits. Because of cross-conjugation, benziporphyrins are not aromatic species. However, protonation of benziporphyrins can afford some aromatic characteristics. Although the synthesis of many examples of monocarbaporphyrins have been successfully executed, no examples of porphyrinoids with pyrene subunits have been prepared. Pyrene-containing porphyrinoids, which have been named as pyreniporphyrins, are theoretically significant molecules that provide insights into the aromaticity and reactivity of porphyrinoid systems.

In this thesis, two projects were conducted to …

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Part I: Photochemical Generation Of Cyclohexyne From A Hydrocarbon Precursor Part Ii: A Triptycenyl Flower, Daniel Maurer Jan 2016

Part I: Photochemical Generation Of Cyclohexyne From A Hydrocarbon Precursor Part Ii: A Triptycenyl Flower, Daniel Maurer

Honors Theses

Part I

Photolysis of phenanthrene-based methylenecyclopropane derivatives have previously been shown to generate alkylidenecarbenes, which readily rearrange to form alkynes. In this work, we show that photolysis of an analogous cyclic alkylidenecarbene precursor at ambi- ent temperature forms cyclohexyne via the putative cyclopentylidenecarbene, and can be trapped by dienes via a Diels-Alder reaction. Cyclohexyne and other strained cycloalkynes are of much interest to theoreticians and experimentalists alike. Results of coupled-cluster and DFT calculations on the potential energy surface of cyclopentylidenecarbene and the corresponding strained cyclohexyne are also presented. The photochemical generation of cy- clopentylidenecarbene, and thus cyclohexyne, from a hydrocarbon …

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