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Studies on the Alternatives to Stilbene Based Precipitons and Further Applications and Designs of Precipitons.

Vaslowski, Gregory (2007) Studies on the Alternatives to Stilbene Based Precipitons and Further Applications and Designs of Precipitons. Master's Thesis, University of Pittsburgh. (Unpublished)

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Precipitons, solubility-based phase tags, can be used in similar fashion to other solution based phase tags without many of the disadvantages. Structures based on azobenzene have been studied as alternatives to stilbene-based precipitons. The double bond between nitrogens in azobenzene can be interconverted between cis and trans by UV irradiation, unlike stilbene which only isomerizes in the cis to trans direction. The analogous nature of azobenzene to stilbene was the basis for the creation and study of possible recyclable alternatives to the studied stilbene orignal. Stilbene-based precipiton reagent tags have also been studied. Previous studies show the effectiveness of precipitons as a substrate tag. To show the precipiton's effectiveness as a reagent scavenger, several carbodiimide-based tags have been synthesized and tested as reagent scavengers. Finally, various sulfoxides tagged with a stilbene-based precipiton have been synthesized in order to demonstrate isolation of small molecules by sublimation from solids. Proof of principle is demonstrated by isomerizing precipiton tagged sulfoxides which are subsequently heated in oil and release several small allyl protected products. These products are isolated and characterized by common methods.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWilcox, Craig Sdaylite@pitt.eduDAYLITE
Committee MemberGrabowski, Joseph Jjoeg@pitt.eduJOEG
Committee MemberNelson, Scott Gsgnelson@pitt.eduSGNELSON
Date: 19 September 2007
Date Type: Completion
Defense Date: 3 August 2007
Approval Date: 19 September 2007
Submission Date: 5 August 2007
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: MS - Master of Science
Thesis Type: Master's Thesis
Refereed: Yes
Uncontrolled Keywords: azo; azobenzene; chemical separations; fluorous; green; organic chemistry; recyclable; scavengers; sythesis; thioureas
Other ID:, etd-08052007-190054
Date Deposited: 10 Nov 2011 19:57
Last Modified: 15 Nov 2016 13:48


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