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Synthesis of hyperbranched poly(aryl amine)s via a carbene insertion approach

Blencowe, A., Fagour, W., Blencowe, C., Cosstick, K. and Hayes, W. (2008) Synthesis of hyperbranched poly(aryl amine)s via a carbene insertion approach. Organic & Biomolecular Chemistry, 6 (13). pp. 2327-2333. ISSN 1477-0520

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To link to this article DOI: 10.1039/b804392m

Abstract/Summary

A novel diazirine functionalised aniline derivative, 3-(3-aminophenyl)-3-methyldiazirine 1, was prepared and employed as an AB(2)-type monomer in the synthesis of hyperbranched polymers; thus providing the first instance in which polyamines have been prepared via carbene insertion polymerisation. Photolysis of the monomer 1 in bulk and in solution resulted in the formation of hyperbranched poly(aryl amine)s with degrees of polymerisation (DP) varying from 9 to 26 as determined by gel permeation chromatography (GPC). In solution, an increase in the initial monomer concentration was generally found to result in a decrease in the molecular weight characteristics of the resulting poly(aryl amine) s. Subsequent thermal treatment of the poly(aryl amine) s caused a further increase in the DP values up to a maximum of 31. Nuclear magnetic resonance (NMR) spectroscopic analysis revealed that the increase in molecular weight upon thermal treatment resulted from hydroamination of styrenic species formed in the initial photopolymerisation or activation of diazirine moieties.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:11040
Uncontrolled Keywords:LASER FLASH-PHOTOLYSIS, POLY(PROPYLENE IMINE) DENDRIMERS, EXCITED TRIPLET DIPHENYLCARBENE, GPC-DISTRIBUTION COEFFICIENTS, RING-OPENING POLYMERIZATION, STAR-SHAPED MOLECULES, THERMAL-DECOMPOSITION, MULTIBRANCHING POLYMERIZATION, 1,2-HYDROGEN MIGRATION, DENDRITIC POLYAMINE

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