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Synthesis and study of perylene-bridge-anchor derivatives for metal oxides semiconductor sensitization
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Fan, Hao. Synthesis and study of perylene-bridge-anchor derivatives for metal oxides semiconductor sensitization. Retrieved from https://doi.org/doi:10.7282/t3-nzt8-z775

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TitleSynthesis and study of perylene-bridge-anchor derivatives for metal oxides semiconductor sensitization
NameFan, Hao (author); Galoppini, Elena (chair); Lockard, Jenny (internal member); Szostak, Michal (internal member); Teplyakov, Andrew V. (outside member); Rutgers University; Graduate School - Newark
Date Created2018
Other Date2018-10 (degree)
SubjectChemistry, Metallic oxides--Synthesis
Extent1 online resource (143 pages) : illustrations
DescriptionElectron transfer at the interface between a photoactive molecule and large-bandgap nanostructured metal oxide (MOn) semiconductors remains at the center of intense research in numerous areas for solar energy conversion. Organic chromophore-bridge-anchor compounds are important to the studies of heterogeneous charge transfer on MOn semiconductors and are widely employed in various photochemistry researches. In this thesis, we report the synthesis of 2,5-di-tert-butylperylene (DTBuPe) and a series of DTBuPe-bridge-anchor compounds, and study their steady state photochemical properties in solutions as well as on nanostructured metal oxide semiconductor films.
The thesis described a practical pathway to synthesize the DTBuPe, and further modification of the DTBuPe framework. Two modification routes were employed; one starting from formylation, which can be followed by reduction, oxidation or other functional group transformation of the aldehyde group. The second route starts from bromination of the framework, followed by various palladium catalyzed cross-coupling reactions. Through these methods, a series of DTBuPe-bridge-anchor derivatives were synthesized.
The spectroscopic properties of DTBuPe-bridge-anchor derivatives in solution and bound to nanostructured semiconductor surfaces were also investigated by absorption and emission spectra. 8,11-di-tert-Butylperylene-3-carboxylic acid (DTBuPe-COOH), 3-(8,11-di-tert-Butylperylen-3-yl)propanoic acid (DTBuPe-Prop-COOH), 4-(8,11-di-tert-Butylperylen-3-yl)benzoic acid (DTBuPe-Ph-COOH) and perylene-3-carboxylic acid (Pe-COOH) were bound to both TiO2 and ZrO2 films and characterized by absorption and emission spectra. A comparison of the properties of DTBuPe-bridge-anchor/TiO2 and perylene/TiO2 is made, and the influence of t-butyl spacing group, as well as different bridge units, is investigated. In addition, perylene was functionalized with an azide group (9-(4-azidophenyl)-2,5-di-tert-Butylperylene (DTBuPe-Ph-N3)) for click chemistry. Copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction of DTBuPe-Ph-N3 was successfully performed in solution and on ZnO nanostructured surfaces which was functionalized with propiolic acid in a stepwise functionalization process. The sensitized ZnO surface was characterized by SEM, XPS and TA. The morphology of ZnO nanorod was preserved and strong electronic coupling between sensitizer and semiconductor film was obtained.
NotePh.D.
NoteIncludes bibliographical references
Noteby Hao Fan
Genretheses, ETD doctoral
Persistent URLhttps://doi.org/doi:10.7282/t3-nzt8-z775
Languageeng
CollectionGraduate School - Newark Electronic Theses and Dissertations
Organization NameRutgers, The State University of New Jersey
RightsThe author owns the copyright to this work.
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