Hydrazine reacts with phthalic anhydride to give a mixture of cyclic hydrazide and N-aminophthalimide. However, the N-aminoimide is exclusively formed in high yield by the reaction of 1,8-naphthalic anhydride with hydrazine. N-aminoimides act as amines and react further with cyclic anhydrides to yield stable bisimides containing an N-N linkage. The syntheses of several bis(N-aminoimide)s from the corresponding bisanhydrides which contain the naphthalic anhydride moiety have been described. Novel high molecular weight polyimides have been synthesized by the reaction of these bis(N-aminoimide)s with cyclic dianhydrides. Most of the polymers are amorphous and are soluble in solvents such as chloroform, o-dichlorobenzene, N-methylpyrrolidinone and m-cresol. Only those polyimides having less flexible groups in their structure or containing a significant amount of perylene units show some degree of crystallinity. / All of the polymers show remarkably high glass transition temperatures, as high as 455$ sp circ$C. Their 5% weight loss by thermogravimetric analysis in an atmosphere of air or nitrogen are all above 440$ sp circ$C. Most of these polymers are highly fluorescent. Their emission spectra are in the visible region and show some evidence for an excited energy transfer and molecular aggregation.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.28451 |
| Date | January 1994 |
| Creators | Ghassemi, Hossein |
| Contributors | Hay, A. S. (advisor) |
| Publisher | McGill University |
| Source Sets | Library and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada |
| Language | English |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Format | application/pdf |
| Coverage | Doctor of Philosophy (Department of Chemistry.) |
| Rights | All items in eScholarship@McGill are protected by copyright with all rights reserved unless otherwise indicated. |
| Relation | alephsysno: 001425395, proquestno: NN00093, Theses scanned by UMI/ProQuest. |
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