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Mass Spectrometric Study of Visible-Light Triggered Photoredox and Electrolytic Reaction Mechanisms

Zhang, Yuexiang
http://rave.ohiolink.edu/etdc/view?acc_num=ohiou1527760864441781

Abstract Details

2018, Master of Science (MS), Ohio University, Chemistry and Biochemistry (Arts and Sciences).
In this thesis, several research projects were conducted, with the focus on using mass spectrometry. First, an online coupling of laser irradiation with electrospray ionization-mass spectrometry (ESI-MS) was used for capturing the intermediates and studying the mechanism of the photoredox reaction. [3+2] annulation reaction of N-cyclopropylaniline (CPA) and styrene was first investigated. In particular, the reactive CPA radical cation, the reduced photocatalyst Ru(I)(bpz)3+, and the [3+2] annulation product radical cation were all successfully detected and confirmed by high-resolution MS. Furthermore, the key step of the proposed chain reaction, the oxidation of CPA to amine radical cation by-product radical cation was successfully confirmed by using the online electrochemical mass spectrometric method. In addition, encouraged by the successful confirmation of chain process by using the electrochemical method, the idea of replacing the photocatalyst by electrosynthesis was established. Online and offline electrosynthesis of CPA and styrene were carried out and the successful detection of the product peak by MS indicated the feasibility of this approach. Also, an online coupling of laser irradiation with electrospray ionization mass spectrometry (ESI-MS) was also used for detecting the intermediates of the aza-Henry reaction of nitromethane with N-aryl-tetrahydroisoquinolines (THIQ). Some important intermediates like THIQ radical cation and THIQ iminium ion were directly captured. In another project, microdialysis tube coupled with LC column to desalt the protein sample for online DESI-MS detection was investigated. Successful detect of the protein signal from a mobile phase containing phosphate buffer suggest this method can remove the salt of protein sample in matrix buffer to improve the MS signal.
Hao Chen (Advisor)
Shiyong Wu (Committee Member)
Harrington Peter , de B (Committee Member)
78 p.
Chemistry
Mass specvtrometry; Photoredox reaction; Electrolytic reaction; Reaction mechanisms

Recommended Citations

Citations

  • Zhang, Y. (2018). Mass Spectrometric Study of Visible-Light Triggered Photoredox and Electrolytic Reaction Mechanisms [Master's thesis, Ohio University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=ohiou1527760864441781

    APA Style (7th edition)

  • Zhang, Yuexiang. Mass Spectrometric Study of Visible-Light Triggered Photoredox and Electrolytic Reaction Mechanisms . 2018. Ohio University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=ohiou1527760864441781.

    MLA Style (8th edition)

  • Zhang, Yuexiang. "Mass Spectrometric Study of Visible-Light Triggered Photoredox and Electrolytic Reaction Mechanisms ." Master's thesis, Ohio University, 2018. http://rave.ohiolink.edu/etdc/view?acc_num=ohiou1527760864441781

    Chicago Manual of Style (17th edition)

ohiou1527760864441781
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© 2018, all rights reserved.
This open access ETD is published by Ohio University and OhioLINK.