Endre søk
RefereraExporteraLink to record
Permanent link

Direct link
Referera
Referensformat
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Annet format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annet språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf
Synthetic Routes towards 2-thia-7,8-diaza-cyclopenta[l]phenanthrene and 1-thia-7,8-diaza-cyclopenta[l]phenanthrene for Molecular Electronics Applications
Mälardalens högskola, Akademin för hållbar samhälls- och teknikutveckling.
2009 (engelsk)Independent thesis Advanced level (degree of Master (One Year)), 20 poäng / 30 hpOppgave
Abstract [en]

Electric current is known to flow through the π-bonds in oligothiophenes. In order to use them as molecular wires it is important to use a technique where the potential gradients can be generated and maintained in supramolecular networks. A solution to this problem can be the use of metal complexes as junction points within such a network.

 In this project pathways to synthesize 2-thia-7,8-diaza-cyclopenta[l]phenanthrene (1) and 1-thia-7,8-diaza-cyclopenta[l]phenanthrene (2) for use in molecular electronic devices have been investigated. 4-(5-Bromo-thiophen-2-yl)2,2’-bipyridine (3) was prepared via Kröhnke reaction from 3-(5-bromothiophene-2-yl)acrolein and 1-(2-Oxo-2-pyridine-2-yl-ethyl)-pyridinium iodide in an overall yield of 14 %.  

 Several routes towards 2-thia-7,8-diaza-cyclopenta[l]phenanthrene (1) and 1-thia-7,8-diaza-cyclopenta[l]phenanthrene (2) were tested. Since the original planned pathway did not work, lack of time made it impossible to complete the series of experiments that were needed. The synthesis of 2-thia-7,8-diaza-cyclopenta[l]phenanthrene (1) is almost finished. Due to the solvation problems, after the decarboxylation step, the product could not be analyzed by 1H-NMR in a satisfactory manner. The product was sent for analysis.

 A number of experiments towards 1-thia-7,8-diaza-cyclopenta[l]phenanthrene (2) were tested but few of them worked as planned. There is a lot of work left to be done in the synthesis of this compound but the lack of time made it impossible.

 The chemistry that has been achieved is the synthesis of 1,10-phenanthroline-5,6-dione in the synthesis of 2-thia-7,8-diaza-cyclopenta[l]phenanthrene (1). The following Hinsberg thiophene synthesis probably worked but due to solvation problems the product could not be isolated. The final product after hydrolysis and decarboxylation of the remaining ester groups after the Hinsberg thiophene synthesis was tested but the results were difficult to confirm.

 In the synthesis of 1-thia-7,8-diaza-cyclopenta[l]phenanthrene (2) several attempts to make 3,4-diamino-N,N-diethyl-benzamide were made. The attack from the primary amines on the carbonyl carbon made it necessary to protect them. The attempt to synthesize 3,4-bis-acetylamino-N,N-diethyl-benzamide also failed, both the attempt directly from the carboxylic acid and through the acylchloride, even though the amines were protected.  

sted, utgiver, år, opplag, sider
2009. , s. 47
Emneord [en]
organic chemistry, molecular electronics
HSV kategori
Identifikatorer
URN: urn:nbn:se:mdh:diva-7505OAI: oai:DiVA.org:mdh-7505DiVA: diva2:277519
Presentation
(engelsk)
Uppsök
Physics, Chemistry, Mathematics
Veileder
Examiner
Tilgjengelig fra: 2009-11-27 Laget: 2009-11-19 Sist oppdatert: 2009-11-27bibliografisk kontrollert

Open Access i DiVA

fulltekst(1652 kB)1618 nedlastinger
Filinformasjon
Fil FULLTEXT01.pdfFilstørrelse 1652 kBChecksum SHA-512
e148f80e08c1b5ed5f7c9fa849754316e4b14fdfad6eeecb5c752d2e0061e6d0ed09664a142ab8025a9b5c9675d860c5ea2c92b2bc65308e716ac9f69e9f9f9e
Type fulltextMimetype application/pdf

Søk i DiVA

Av forfatter/redaktør
Grandin, Anna
Av organisasjonen

Søk utenfor DiVA

GoogleGoogle Scholar
Totalt: 1618 nedlastinger
Antall nedlastinger er summen av alle nedlastinger av alle fulltekster. Det kan for eksempel være tidligere versjoner som er ikke lenger tilgjengelige

urn-nbn

Altmetric

urn-nbn
Totalt: 899 treff
RefereraExporteraLink to record
Permanent link

Direct link
Referera
Referensformat
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Annet format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annet språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf