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Thesis Shanshan WU-2.pdf (2.14 MB)

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Development of Conjugated Low-coordinate Organophosphorus Materials

WU, Shanshan
http://rave.ohiolink.edu/etdc/view?acc_num=case1396603528

Abstract Details

2014, Doctor of Philosophy, Case Western Reserve University, Chemistry.
Organophosphorus conjugated materials featuring P=C units have been studied in recent years due to their unique optoelectronic properties, which may possibly find use in OLEDs and other optoelectronic devices. Previous study on 1,3-benzoxaphospholes (BOPs) revealed their highly fluorescent nature. In order to facilitate employment of these types of materials into devices, we sought to increase the stability and solubility of benzoxaphospholes by introduction of a sterically demanding tert-butyl group ortho to the low coordinate phosphorus center. In the first part of this work, reaction precursor 3,5-di-tert-butyl-2-phosphinophenol was prepared and characterized. But the presence of a sterically demanding tert-butyl group adjacent to the PH2 renders the molecule more air sensitive than 2-phosphinophenol. Investigations into the stability of this bulky substituted phosphinophenol were conducted. The second part of this presented work is the synthesis and characterization of a group of sterically hindered 1,3-benzoxaphospholes. Those compounds displayed comparable photoluminescence and enhanced stability than the less bulky 1,3-benzoxaphospholes. Furthermore we have been working on the incorporation of BOP units into extended conjugated systems. A series of bisbenzoxaphospholes and a tribenzoxaphosphole were synthesized and characterized. In the third part, an unusual phospha-Fries rearrangement reaction of diethyl (2,3,5-trimethylphenyl)phosphate to yield diethyl (2-hydroxy-4,6-dimethylbenzyl)phosphonate was discovered in the preliminary work. This new phosphonate could be reduced to 3,5-dimethyl-2-phosphanylmethylphenol, which then could be used to make novel six-membered heterocyclic compounds containing a P=C bond. Azaphospholes have been used in coordination chemistry. However, the literature has no examples of luminescent azaphosphole. Due to the rigid structure of carbazole, we have interest in using it as a template to synthesize luminescent carbazole-based azaphospholes. In this work, synthetic strategies for carbazole-based azaphosphole will be explored.
John Protasiewicz (Advisor)
Malcolm Kenney (Committee Chair)
Anthony Pearson (Committee Member)
Genevieve Sauve (Committee Member)
Lei Zhu (Committee Member)
230 p.
Chemistry
Conjugated materials; low-coordinate organophosphorus

Recommended Citations

Citations

  • WU, S. (2014). Development of Conjugated Low-coordinate Organophosphorus Materials [Doctoral dissertation, Case Western Reserve University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=case1396603528

    APA Style (7th edition)

  • WU, Shanshan. Development of Conjugated Low-coordinate Organophosphorus Materials. 2014. Case Western Reserve University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=case1396603528.

    MLA Style (8th edition)

  • WU, Shanshan. "Development of Conjugated Low-coordinate Organophosphorus Materials." Doctoral dissertation, Case Western Reserve University, 2014. http://rave.ohiolink.edu/etdc/view?acc_num=case1396603528

    Chicago Manual of Style (17th edition)

case1396603528
413
© 2014, all rights reserved.
This open access ETD is published by Case Western Reserve University School of Graduate Studies and OhioLINK.