| dc.identifier.uri | http://hdl.handle.net/11401/77097 | |
| 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 | Thesis | |
| dcterms.abstract | All-carbon materials have been widely investigated because of their potential thermal, electrical and physical properties. Carbyne, which would have all sp hybridized carbons, has received considerable attention. Polydiiododiacetylene (PIDA), which has a carbon backbone and iodine atom substituents, serves as a potential precursor to carbyne. We propose that carbyne could result from complete deiodination of PIDA in the presence of Lewis bases such as triethyl amine, pyridine and pyrrolidine. To avoid aggregation of PIDA or carbyne strands during this process, we aim to prepare PIDA as a polyrotaxane through topochemical polymerization, using a macrocyclic cocrystallizing agent, or " host" , containing pyridine segments. In this work, the structure and synthesis of macrocyclic host have been thoroughly investigated. The conformation of the macrocyclic host was optimized through equilibrium conformer using the AM1 semi-empirical modeling and multiple possible conformations were proposed to predict the macrocyclic rings' sizes. A route was chosen to synthesize the target macrocyclic host, which has four main segments; glycol ether group, pyridyl, alkynyl and oxalyl group. This route includes Sonogashira coupling with 4-pentyn-1-ol, tosylation of hydroxyl, substitution of tosyl group, Staudinger reaction and coupling with ethyl oxalyl chloride. This synthetic route has been pursued and all intermediates were successfully synthesized. | |
| dcterms.available | 2017-09-20T16:51:57Z | |
| dcterms.contributor | Lauher, Joseph | en_US |
| dcterms.contributor | Goroff, Nancy S. | en_US |
| dcterms.contributor | Dreuckhammer, Dale. | en_US |
| dcterms.creator | Chen, Ce | |
| dcterms.dateAccepted | 2017-09-20T16:51:57Z | |
| dcterms.dateSubmitted | 2017-09-20T16:51:57Z | |
| dcterms.description | Department of Chemistry. | en_US |
| dcterms.extent | 83 pg. | en_US |
| dcterms.format | Monograph | |
| dcterms.format | Application/PDF | en_US |
| dcterms.identifier | http://hdl.handle.net/11401/77097 | |
| dcterms.issued | 2014-12-01 | |
| dcterms.language | en_US | |
| dcterms.provenance | Made available in DSpace on 2017-09-20T16:51:57Z (GMT). No. of bitstreams: 1
Chen_grad.sunysb_0771M_11900.pdf: 3009382 bytes, checksum: 7ef3af9fa17a495f82900abdfd75c577 (MD5)
Previous issue date: 1 | en |
| dcterms.publisher | The Graduate School, Stony Brook University: Stony Brook, NY. | |
| dcterms.subject | Carbyne, Polydiiododiacetylene, Topochemical polymerization | |
| dcterms.subject | Chemistry | |
| dcterms.title | Macrocyclic Hosts for Polymerization of Diiodobutadiyne | |
| dcterms.type | Thesis | |
