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Synthesis of Novel Conjugated Materials – Push-Pull Conjugated Diynes and 1,7-Phenanthroline Derivatives

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dc.contributor.advisor Goroff, Nancy S en_US
dc.contributor.author Ang, Xiuzhu en_US
dc.contributor.other Department of Chemistry. en_US
dc.date.accessioned 2017-09-20T16:51:54Z
dc.date.available 2017-09-20T16:51:54Z
dc.date.issued 2015-12-01
dc.identifier.uri http://hdl.handle.net/11401/77082 en_US
dc.description 270 pg. en_US
dc.description.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%. en_US
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 en_US
dc.format.medium Electronic Resource en_US
dc.language.iso en_US en_US
dc.publisher The Graduate School, Stony Brook University: Stony Brook, NY. en_US
dc.subject.lcsh Organic chemistry en_US
dc.subject.other 1,7-phenanthroline derivatives, HBL, Push-pull diynes, Push-pull PDA en_US
dc.title Synthesis of Novel Conjugated Materials – Push-Pull Conjugated Diynes and 1,7-Phenanthroline Derivatives en_US
dc.type Dissertation en_US
dc.mimetype Application/PDF en_US
dc.contributor.committeemember Rudick, Jonathan en_US
dc.contributor.committeemember Lauher, Joseph en_US
dc.contributor.committeemember Yager, Kevin. en_US


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