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Dye Molecule-Based Porous Organic Materials

Eder, Grace M
http://rave.ohiolink.edu/etdc/view?acc_num=osu1530012900215452

Abstract Details

2018, Doctor of Philosophy, Ohio State University, Chemistry.
Porous materials are an ever-expanding area of materials science well known for their highly porous structures, which are well suited to hosting a variety of guests from small compounds such as gasses to large complex molecules. Additionally, porous materials can be rationally designed prior to synthesis to incorporate monomers with desired functionalities, which makes them amenable to a variety of applications including gas storage and uptake, sensing, catalysis, and optoelectronics. Our interest has been to bring functional monomers, such as dye molecules, into porous polymers for applications geared toward alternative energy. One class of dye we found intriguing were subphthalocyanines (SubPcs), which have an unusual 3-dimensional shape and excellent optoelectronic properties. SubPcs are often incorporated into organic photovoltaics in the small molecule form, and have achieved good power conversion efficiencies up to 7%. We envisioned that incorporation of a SubPc into a polymer might have useful function in an optoelectronic application. We synthesized a boronate ester linked SubPc-based polymer, fully characterized its structure and tested its ability in optoelectronic applications. The boronate ester linkage has been a mainstay in the field of porous polymers, especially covalent organic frameworks (COFs). Despite its success in the early development of COFs, the boronate ester linkage suffers from a significant drawback of instability to small amounts of water. The field of COFs has been shifting away from the boronate ester linkage in favor of more chemically stable linkages that can still afford crystalline materials. One such linkage has been developed in our laboratory, the benzobisoxazole (BBO) linkage. We have shown the BBO linkage yields crystalline materials with good stability in water. However since the BBO linkage is a relatively new development in the field of COFs not much is known about how this linkage promotes crystallinity in COF materials. We undertook a comprehensive study of the different factors at work during the formation of BBO linked COF materials to gain some insights on this process. With the development of this stable BBO linkage, we wanted to show its utility by incorporating it into a functional material. We targeted a heterogeneous catalysis application to aid in the development of an important reaction, the reduction of CO2 to useful compounds. We decided to incorporate another dye functionality, a porphyrin, to act as a catalytic site for the hydrosilylation of CO2. We created porphyrin-based porous polymers both with, and without a metal ion in the central cavity of the porphyrin, then characterized these materials and evaluated their efficacy in catalyzing the hydrosilylation of CO2 to transform it into more useful chemical feedstocks.
Psaras McGrier (Advisor)
Jovica Badjic (Committee Member)
Jon Parquette (Committee Member)
244 p.
Chemistry; Materials Science; Polymers
dyes; porphyrins; subphthalocyanines; polymers porous; materials; optoelectronic; photovoltaic; catalysis; CO2 conversion; environmental; fuels; alternative energy;

Recommended Citations

Citations

  • Eder, G. M. (2018). Dye Molecule-Based Porous Organic Materials [Doctoral dissertation, Ohio State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=osu1530012900215452

    APA Style (7th edition)

  • Eder, Grace. Dye Molecule-Based Porous Organic Materials. 2018. Ohio State University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=osu1530012900215452.

    MLA Style (8th edition)

  • Eder, Grace. "Dye Molecule-Based Porous Organic Materials." Doctoral dissertation, Ohio State University, 2018. http://rave.ohiolink.edu/etdc/view?acc_num=osu1530012900215452

    Chicago Manual of Style (17th edition)

osu1530012900215452
223
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This open access ETD is published by The Ohio State University and OhioLINK.