Synthesis of Novel Conjugated Materials – Push-Pull Conjugated Diynes and 1,7-Phenanthroline Derivatives
Synthesis of Novel Conjugated Materials – Push-Pull Conjugated Diynes and 1,7-Phenanthroline Derivatives
| dc.identifier.uri | http://hdl.handle.net/11401/77082 | |
| dc.description.sponsorship | This work is sponsored by the Stony Brook University Graduate School in compliance with the requirements for completion of degree. | en_US |
| dc.format | Monograph | |
| dc.format.medium | Electronic Resource | en_US |
| dc.language.iso | en_US | |
| dc.publisher | The Graduate School, Stony Brook University: Stony Brook, NY. | |
| dc.type | Dissertation | |
| dcterms.abstract | This thesis is composed of two separate sections, focusing on developing novel conjugated materials. The first section describes attempts towards synthesis of push-pull polydiacetylenes (PDAs), substituted by alternating electron-rich and electron-poor groups. These polymers are expected to have extensive conjugation and low energy band gaps, and therefore potential application in organic photovoltaic cells and nonlinear optics. We targeted push-pull PDAs by solid-state polymerization of appropriate diyne monomers. Oxalamide host molecules containing Lewis acidic or basic side groups are introduced to pre-organize the push-pull diynes in a co-crystal scaffold through Lewis acid-base interactions. Several novel diynes with iodine as electron donor and nitrile or carboxylic acid as electron acceptor have been synthesized. One co-crystal, containing 4-(iodobuta-1,3-diyn-1-yl)benzoic acid as the monomer and bis(pyridyl) oxalamide as the host, has been prepared successfully. The co-crystal has ruby color. Its structure is determined by single-crystal XRD. However, the monomers in the co-crystal do not have appropriate geometry for solid-state polymerization. The second section focuses on developing tunable hole-blocking layers (HBL) in new CIGS-based thin-film solar cells, in collaboration with the Eisaman group at Brookhaven National Laboratory. 1,7-Phenanthroline derivatives are targeted as novel HBL materials for their large energy band gap, tunable energy levels and morphologies. Several aryl/alkyl substituted 1,7-phenanthroline derivatives have been synthesized. 2,8-Dimethyl-1,7-phenanthroline is considered the most promising HBL material among all synthesized compounds for having both large energy band gap and powdery morphology. Both organic and CIGS photovoltaic devices containing 2,8-dimethyl-1,7-phenanthroline as HBL were fabricated in collaboration with the Kymissis group at Columbia University. According to the efficiency measured under AM1.5G illumination, including a HBL can enhance the PCE of the organic device from 0.9 to 5.0%, and the CIGS device from 3.2×10−4 to 0.11%. | |
| dcterms.abstract | This thesis is composed of two separate sections, focusing on developing novel conjugated materials. The first section describes attempts towards synthesis of push-pull polydiacetylenes (PDAs), substituted by alternating electron-rich and electron-poor groups. These polymers are expected to have extensive conjugation and low energy band gaps, and therefore potential application in organic photovoltaic cells and nonlinear optics. We targeted push-pull PDAs by solid-state polymerization of appropriate diyne monomers. Oxalamide host molecules containing Lewis acidic or basic side groups are introduced to pre-organize the push-pull diynes in a co-crystal scaffold through Lewis acid-base interactions. Several novel diynes with iodine as electron donor and nitrile or carboxylic acid as electron acceptor have been synthesized. One co-crystal, containing 4-(iodobuta-1,3-diyn-1-yl)benzoic acid as the monomer and bis(pyridyl) oxalamide as the host, has been prepared successfully. The co-crystal has ruby color. Its structure is determined by single-crystal XRD. However, the monomers in the co-crystal do not have appropriate geometry for solid-state polymerization. The second section focuses on developing tunable hole-blocking layers (HBL) in new CIGS-based thin-film solar cells, in collaboration with the Eisaman group at Brookhaven National Laboratory. 1,7-Phenanthroline derivatives are targeted as novel HBL materials for their large energy band gap, tunable energy levels and morphologies. Several aryl/alkyl substituted 1,7-phenanthroline derivatives have been synthesized. 2,8-Dimethyl-1,7-phenanthroline is considered the most promising HBL material among all synthesized compounds for having both large energy band gap and powdery morphology. Both organic and CIGS photovoltaic devices containing 2,8-dimethyl-1,7-phenanthroline as HBL were fabricated in collaboration with the Kymissis group at Columbia University. According to the efficiency measured under AM1.5G illumination, including a HBL can enhance the PCE of the organic device from 0.9 to 5.0%, and the CIGS device from 3.2×10−4 to 0.11%. | |
| dcterms.available | 2017-09-20T16:51:54Z | |
| dcterms.contributor | Goroff, Nancy S | en_US |
| dcterms.contributor | Rudick, Jonathan | en_US |
| dcterms.contributor | Lauher, Joseph | en_US |
| dcterms.contributor | Yager, Kevin. | en_US |
| dcterms.creator | Ang, Xiuzhu | |
| dcterms.dateAccepted | 2017-09-20T16:51:54Z | |
| dcterms.dateSubmitted | 2017-09-20T16:51:54Z | |
| dcterms.description | Department of Chemistry. | en_US |
| dcterms.extent | 270 pg. | en_US |
| dcterms.format | Application/PDF | en_US |
| dcterms.format | Monograph | |
| dcterms.identifier | http://hdl.handle.net/11401/77082 | |
| dcterms.issued | 2015-12-01 | |
| dcterms.language | en_US | |
| dcterms.provenance | Made available in DSpace on 2017-09-20T16:51:54Z (GMT). No. of bitstreams: 1 Ang_grad.sunysb_0771E_12628.pdf: 9496728 bytes, checksum: b60216f05b2f3b86c7b97a15c2e19498 (MD5) Previous issue date: 1 | en |
| dcterms.publisher | The Graduate School, Stony Brook University: Stony Brook, NY. | |
| dcterms.subject | 1,7-phenanthroline derivatives, HBL, Push-pull diynes, Push-pull PDA | |
| dcterms.subject | Organic chemistry | |
| dcterms.title | Synthesis of Novel Conjugated Materials – Push-Pull Conjugated Diynes and 1,7-Phenanthroline Derivatives | |
| dcterms.title | Synthesis of Novel Conjugated Materials – Push-Pull Conjugated Diynes and 1,7-Phenanthroline Derivatives | |
| dcterms.type | Dissertation |
