Skip to Main Content
 

Global Search Box

 
 
 
 

Files

File List


Final Dissertation.pdf (20.07 MB)

ETD Abstract Container

Abstract Header

Photocyclodehydrofluorination (PCDHF) – A synthetic method for fluorinated polynuclear aromatic hydrocarbons

LI, ZHE
http://rave.ohiolink.edu/etdc/view?acc_num=kent1448814689

Abstract Details

2015, PHD, Kent State University, College of Arts and Sciences / Department of Chemistry.
The Mallory type photocyclization involves a series of photoreactions of stilbenes and stilbene-like derivatives which undergo intramolecular cyclization, forming dihydrophenanthrenes and their derivatives under appropriate UV irradiation. In typical Mallory photocyclizations, appropriate oxidants or leaving groups are usually needed to accomplish the overall process. In our research, the fluorine atom functions as an unusual leaving group, introducing a new type of Mallory type photocyclization reaction – the photocyclodehydrofluorination (PCDHF). Fluorinated stilbenes and their derivatives undergo ring closures, which could be a very useful to produce a large range of fluorinated polynuclear aromatic hydrocarbons that possess a phenanthrene (or heterocyclic analogue of phenanthrene) substructure. This PCDHF method could permit the construction of more extensive structures with high crystal cofaciality and close packing of interest as high mobility organic semiconductors. This methodology, when coupled with other complementary approaches to produce highly fluorinated aromatics and the functionalization of existing perfluoroaromatics should become a formidable arsenal to prepare such materials.
Robert Twieg (Advisor)
Scott Bunge (Committee Member)
Paul Sampson (Committee Member)
Liang-Chy Chien (Committee Member)
Brett Ellman (Committee Member)
568 p.
Chemistry; Materials Science; Molecules
photocyclodehydrofluorination; photoreaction; Mallory type photocyclization; fluorine; material; liquid crystal; IR transparency

Recommended Citations

Citations

  • LI, Z. (2015). Photocyclodehydrofluorination (PCDHF) – A synthetic method for fluorinated polynuclear aromatic hydrocarbons [Doctoral dissertation, Kent State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=kent1448814689

    APA Style (7th edition)

  • LI, ZHE. Photocyclodehydrofluorination (PCDHF) – A synthetic method for fluorinated polynuclear aromatic hydrocarbons. 2015. Kent State University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=kent1448814689.

    MLA Style (8th edition)

  • LI, ZHE. "Photocyclodehydrofluorination (PCDHF) – A synthetic method for fluorinated polynuclear aromatic hydrocarbons." Doctoral dissertation, Kent State University, 2015. http://rave.ohiolink.edu/etdc/view?acc_num=kent1448814689

    Chicago Manual of Style (17th edition)

kent1448814689
453
© 2015, all rights reserved.
This open access ETD is published by Kent State University and OhioLINK.