Link to the University of Pittsburgh Homepage
Link to the University Library System Homepage Link to the Contact Us Form

Development of Fluorescein-Based Fluorescent Chemosensors and Convergent Approaches in Solid-Phase Organic Synthesis

Garner, Amanda Lee (2009) Development of Fluorescein-Based Fluorescent Chemosensors and Convergent Approaches in Solid-Phase Organic Synthesis. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

Primary Text

Download (20MB) | Preview


Palladium and platinum are widely used precious metals that play a pivotal role in energy, materials and drugs. Using a common principle of fluorescent sensor design, a highly sensitive fluorescent detection method for these metals has been developed. A key aspect of this method is the amplification of fluorescence signal directly through a catalytic process, which is conceptually new for metal sensors. Using this method, sub-ppb levels of these metals can be detected with potential applications in the pharmaceutical industry, hospitals and pharmacies. As an extensive of this palladium- and platinum-specific fluorescent sensor, determination of the oxidation state of palladium and platinum based on the aromatic Claisen rearrangement is also demonstrated. Using this mechanism, the probe can fluorescently distinguish Pd0 from PdII/IV and Pt0 from PtIV in both organic and aqueous solvents. Ozone exposure is a significant global health problem, especially in urban areas. While ozone in the stratosphere protects the earth from damaging ultraviolet light, tropospheric is toxic resulting in damage to the respiratory tract. In addition, tt has recently been shown that ozone may be produced endogenously in inflammation and antibacterial responses of the immune system; however, these results have sparked controversy due to the use of a non-specific colorimetric probe. A fluorescent sensor capable of unambiguously detecting ozone has been developed. This is the first sensor that is specific for ozone and can be used in both biological and atmospheric samples. Solid-phase organic synthesis is an enabling technology and its automation has profoundly impacted the scientific community and society in general. However, to date, the structural diversity of the molecules that can be synthesized by this technology is limited partly because current solid-phase organic synthesis relies on linear approaches. Described here are efforts toward the development of an enabling resin-to-resin olefin cross-metathesis technology that unites two functionalized alkene fragments to form highly complex small molecules in a convergent manner. It is also demonstrated that olefin cross-metathesis is a synthetically viable method particularly when a traceless longer linker is inserted between solid support and reacting olefins.


Social Networking:
Share |


Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Garner, Amanda Leeamg27@pitt.eduAMG27
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairKoide, Kazunorikoide@pitt.eduKOIDE
Committee MemberDay, Billy Wbday@pitt.eduBDAY
Committee MemberBrummond, Kaykbrummon@pitt.eduKBRUMMON
Committee MemberWeber, Stephen Gsweber@pitt.eduSWEBER
Date: 9 February 2009
Date Type: Completion
Defense Date: 25 September 2008
Approval Date: 9 February 2009
Submission Date: 9 October 2008
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: PhD - Doctor of Philosophy
Thesis Type: Doctoral Dissertation
Refereed: Yes
Uncontrolled Keywords: fluorescence; organic synthesis; ozone; palladium; platinum; sensors; solid-phase
Other ID:, etd-10092008-183311
Date Deposited: 10 Nov 2011 20:02
Last Modified: 15 Nov 2016 13:50


Monthly Views for the past 3 years

Plum Analytics

Actions (login required)

View Item View Item